Chicago Hotels from S$224 - Top Hotel & deals for the perfect getaway

A river with a yellow boat, surrounded by tall buildings and a bridge.

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Where to stay in Chicago?

Properties are selected based on real traveller reviews and popularity among guests who’ve booked a night in Chicago on Hotels.com. These Chicago hotels consistently deliver on quality, location and traveller experience. Last updated on 28 September 2026.

A marble-floored lobby with double doors and elevators, each marked with a 'CQ' sign.

A man in a suit sitting by a window with a vase of red flowers.

A hotel room with a grey sofa, a bed with a white mattress, a wooden dresser, and a large window with curtains.

A conference room with a long table, chairs, and a vase.

1. River Hotel

Downtown Chicago

S$282

includes taxes & fees

25 Oct - 26 Oct

A spacious lobby with a central sofa, multiple seating areas, and a decorative ceiling.

A cityscape with various buildings, including a prominent skyscraper and a classical building with arched windows.

A grand ballroom with ornate ceiling decorations, multiple chandeliers, and a central table with a white tablecloth.

A spacious bar area with a central bar, multiple seating options including bar stools and tables, and a well-lit ceiling with recessed lighting.

2. Congress Plaza Hotel

Downtown Chicago

S$227

includes taxes & fees

26 Oct - 27 Oct

A spacious lobby with a central coffee table, sofas, and a large mirror.

A spacious lobby with high ceilings, large arched windows, and a grand staircase.

A balcony with a table set for a meal, featuring a charcuterie board and two glasses of wine, overlooking a cityscape.

A spacious lounge area with leather sofas, round tables, and comfortable chairs, featuring a wooden ceiling and elegant decor.

3. The Chicago Hotel Collection Ambassador Gold Coast

Downtown Chicago

S$272

includes taxes & fees

14 Oct - 15 Oct

The Riu Plaza Chicago Hotel facade with a grand entrance, large windows, and a modern architectural design.

A modern hotel lobby with a central seating area, a reception desk, and a decorative wall with a unique design.

A spacious lobby with a marble floor, a reception desk, and a glass partition.

A couple dining at a table with a city view, surrounded by chairs and a variety of dishes.

4. Hotel Riu Plaza Chicago

Downtown Chicago

S$395

includes taxes & fees

25 Oct - 26 Oct

An outdoor rooftop lounge with seating, a fire feature, and a view of the city skyline at night.

A modern lounge area with leather sofas, wooden coffee tables, and ambient lighting.

A modern lobby with a wooden ceiling, leather sofas, and a coffee bar.

A rooftop venue with white chairs and a sofa, draped with white fabric and floral arrangements, overlooking a cityscape.

5. The Chicago Hotel Collection - Magnificent Mile

Downtown Chicago

S$245

includes taxes & fees

25 Oct - 26 Oct

A spacious hotel lobby with a bar area, dining tables, and a central seating area.

A hotel with a classic facade, multiple flags, and a prominent entrance.

A modern living room with a fireplace, leather armchairs, a sofa, and a coffee table.

6. The Allegro Royal Sonesta Hotel Chicago Loop

Downtown Chicago

S$329

includes taxes & fees

25 Oct - 26 Oct

A room with two chairs and a small table, a large window with a city view at night.

A bar area with a long counter, multiple stools, and a television screen.

A modern bar area with a circular seating arrangement, a staircase leading to an upper level, and a view of the city through large windows.

A modern living room with a sectional sofa, a round ottoman, a dining area with chairs and a table, and a large mirror on the wall.

7. Eurostars Magnificent Mile

Downtown Chicago

S$321

includes taxes & fees

29 Oct - 30 Oct

A person relaxing on a sofa with a laptop, a glass of red wine, and a small table with a vase of flowers and a telephone.

A bar area with a long counter, multiple shelves of bottles, and four bar stools.

A room with a bed against a window overlooking a cityscape. There is a small table with a book, a vase with flowers, and a cup.

A modern hotel lobby with leather sofas, a coffee table, and a floor lamp.

8. L7 Chicago by LOTTE

Downtown Chicago

S$440

includes taxes & fees

1 Oct - 2 Oct

A spacious bar area with high ceilings and large windows, offering views of a cityscape.

A hotel room with a bed, a sofa with cushions, a large window with a view of a cityscape and water.

A bar with a circular liquor display, seating with stools, and a city view through large windows.

A multi-level hotel lobby with a glass elevator, a seating area, and a dining space.

9. Hyatt Regency Chicago

Downtown Chicago

S$525

includes taxes & fees

24 Oct - 25 Oct

A large, historic building with a central courtyard surrounded by trees.

A marina with numerous boats docked, surrounded by a cityscape with high-rise buildings and a stadium.

A modern hotel lobby with a curved white sofa, two side tables with lamps, a black coffee table, and a large chandelier.

A restaurant interior with wooden tables and chairs, a carpeted floor, and framed pictures on the walls.

10. Hilton Chicago

Downtown Chicago

S$281

includes taxes & fees

24 Oct - 25 Oct

A luxurious hotel lobby with a plush sofa set, a large wooden bookshelf, and a central decorative pillar.

A warmly lit library with bookshelves, a central reading area with sofas and a table, and a chandelier.

A reception area with a wooden counter, shelves with various items, and a decorative wall hanging.

A bar area with a staircase leading up to it, surrounded by potted plants.

11. Freehand Chicago

Downtown Chicago

S$300

includes taxes & fees

7 Oct - 8 Oct

A cityscape at dusk with high-rise buildings, including a Hilton hotel.

A dining table set for a meal with a floral centerpiece, surrounded by chairs, in a room with a cityscape view.

A hotel room with a sofa, armchair, a flat-screen TV, a bed, and a view of the city and ocean.

A hotel room with a bed, a desk, a television, a sofa, and a large window with a city view.

12. Hilton Chicago/Magnificent Mile Suites

Downtown Chicago

S$265

includes taxes & fees

25 Oct - 26 Oct

A building with a sign reading "111" and "III West Adams Street" indicating a pub and restaurant.

A hotel room with a large window, a bed, and a suitcase.

A modern living room with a fireplace, leather sofas, and a wooden floor.

A restaurant interior with brick walls, wooden tables and chairs, and a bar area.

13. Club Quarters Hotel, Central Loop, Chicago

Downtown Chicago

S$225

includes taxes & fees

25 Oct - 26 Oct

A rooftop terrace with outdoor seating, a view of the city skyline, and a river.

A modern hotel room with a large bed, a desk, a sofa, and a view of the city.

A modern hotel room with a desk, a sofa, a coffee machine, a TV, and a unique wall art piece.

A modern living room with a sofa, coffee table, and ottoman, a fireplace, and a large window with a city view.

14. LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

S$420

includes taxes & fees

25 Oct - 26 Oct

A dining area with a table set for four, large windows offering a cityscape view at dusk.

A modern interior with a central fireplace, seating area, and wall-mounted lighting.

A high-rise hotel room with large windows offering a city view, round tables set for dining, and elegant decor with flowers and candles.

A rooftop terrace with outdoor seating and a fire pit, overlooking a cityscape with tall buildings.

15. The Royal Sonesta Chicago Downtown

Downtown Chicago

S$404

includes taxes & fees

29 Oct - 30 Oct

The Intercontinental hotel facade with a large American flag and a floral display.

A bar area with a high bar counter, multiple stools, and a seating area with booths and tables.

A person sitting by a window with a cityscape view.

A swimming pool area with a glass-bottomed pool, a high ceiling with hanging lights, and a staircase with people sitting on it.

16. InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago

S$444

includes taxes & fees

25 Oct - 26 Oct

A balcony with a table and chairs, a bottle of wine, and a glass of wine.

A hotel lobby with a revolving door, a reception desk, and a waiting area with seating.

A high-rise building with multiple floors, large windows, and balconies.

A modern living room with a sofa, a coffee table, a laptop, and a city view through large windows.

17. Kasa Magnificent Mile Chicago

Downtown Chicago

A hotel room with a large window, a bed, a desk, a chair, and a lamp.

A tall, modern hotel with a brick facade and numerous windows.

18. Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Downtown Chicago

S$267

includes taxes & fees

27 Oct - 28 Oct

A modern building with a colorful facade and a red circular seating area.

A modern interior with wooden shelves, colorful chairs, and hanging plants.

A modern bar area with a checkered floor, wooden ceiling, and various bar equipment.

A modern hotel room with a large window offering a city view, a contemporary light fixture, and a clean, minimalist design.

19. citizenM Chicago Downtown

Downtown Chicago

S$313

includes taxes & fees

25 Oct - 26 Oct

A modern rooftop lounge with white seating, a glass ceiling, and city views.

A rooftop bar with a city skyline view, wooden flooring, and bar stools.

A modern building with a unique architectural design, featuring a mix of glass and concrete materials.

A modern hotel room with a cityscape view, a bed, a desk, a coffee machine, and a purple sofa.

20. The Godfrey Hotel Chicago

Downtown Chicago

S$408

includes taxes & fees

4 Oct - 5 Oct

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A multi-story building with a brick facade, a well-maintained lawn, and a black metal fence.

A staircase with red carpet, wooden paneling on the walls, and a bar area with stools.

A cozy lounge area with leather sofas, a central coffee table, and a fireplace.

A bar area with a dark blue brick wall, wooden slats, and a counter with two chairs.

The Majestic Hotel

Lakeview

S$29 off

S$258

for 1 room

includes taxes & fees

A hotel room with a large window offering a city view, two armchairs, a bed, and a lamp.

A hotel room with a sofa, two armchairs, a coffee table, a TV, and a city view.

A hotel hallway with a patterned carpet, framed artwork on the walls, and a skylight ceiling.

Jaslin Hotel

Chinatown

S$16 off

S$302

for 1 room

includes taxes & fees

A hotel room with a bed, a desk, a television, and a window with a view of buildings.

A well-appointed lounge area with a fireplace, leather armchairs, and a checkered floor.

A dining area with four tables and chairs, each with a small plant. There are two framed artworks on the walls.

The Willows Hotel

Lakeview

S$28 off

S$255

for 1 room

includes taxes & fees

A courtyard with a fire pit, outdoor seating, and a building with a balcony.

A modern indoor swimming pool with clear blue water, surrounded by tiled flooring and equipped with multiple lounge chairs and tables.

A self-service snack and beverage kiosk with a microwave, refrigerated section, and a variety of snacks and drinks.

A spacious lobby with a modern chandelier, seating areas, and a large wall-mounted artwork.

Courtyard by Marriott Chicago Midway Airport

Bedford Park

S$282

for 1 room

includes taxes & fees

A modern interior with a sofa, a coffee table, and a wall of wine bottles.

A cozy bar area with a wooden counter, cushioned seating, and a brick wall backdrop.

A bedroom with a brick wall, a bed with white bedding, a nightstand with a lamp, and a framed sign that reads "NO LIGHTS! IN WRIGLEYVILLE".

The Chicago Hotel Collection entrance with a marquee sign and two red buttons on the wall.

The Chicago Hotel Collection - Wrigleyville

Lakeview

S$58 off

S$282

for 1 room

includes taxes & fees

A hotel bathroom with a large mirror, a sink, and a vanity.

A gym with various exercise equipment, including treadmills and weight machines.

A hotel with a classic facade, large windows, and a prominent entrance.

A bakery display with pastries and a coffee shop sign in the background.

Sports Illustrated Resorts Chicago

Downtown Chicago

S$90 off

S$567

for 1 room

includes taxes & fees

A bar area with a counter, menu boards, and a unique seating arrangement with numbered stools.

A reception area with a counter, seating, and lockers.

A modern room with bunk beds, a sofa, a round coffee table, and a view of the city through large windows.

A modern hotel room with bunk beds, a kitchen area, and a seating space with a round table.

The Chicago Hotel Collection River North

Downtown Chicago

S$295

for 1 room

includes taxes & fees

A couple sitting on a blue couch with a table in front of them, holding drinks and a pizza.

A hotel room with two beds, a window with curtains, a bedside table with a lamp, and a small ottoman.

A laundry area with a washing machine, a dryer, and an ice dispenser.

A person sitting on a blue couch with a dog beside them, holding a glass of wine, and a pizza on a wooden board on a table.

Hotel Saint Clair- Magnificent Mile

Downtown Chicago

S$150 off

S$450

for 1 room

includes taxes & fees

A building with a stone facade and large glass windows.

A room with a white wardrobe, a grey sofa, and a mirror on the wall.

A room with a large window, a patterned armchair, and a view of a cityscape with buildings and a street.

A hotel room with a large bed, two bedside tables with lamps, a chair, and a city view through large windows.

Ohio House Motel

Downtown Chicago

S$407

for 1 room

includes taxes & fees

Freehand Chicago

Downtown Chicago

S$66 off

S$397

for 1 room

includes taxes & fees

A hotel room with a large bed, a desk, a chair, a nightstand, a lamp, and a mirror.

Chicago Lake Shore Hotel

Kenwood

S$254

for 1 room

includes taxes & fees

A modern hotel lobby with a reception desk, marble flooring, and elegant chandeliers.

A modern living room with a dark sofa set, a glass coffee table, and a decorative chandelier.

A man and a woman walking down a marble staircase in a hotel lobby with a chandelier and a sign indicating an exit.

A modern bar area with a bar counter, multiple stools, and a chandelier.

Silversmith Hotel Chicago Downtown

Downtown Chicago

S$59 off

S$571

for 1 room

includes taxes & fees

A modern kitchen with a large island, bar stools, and a city view.

A modern dining area with a wooden table and chairs, a central sink, and large windows.

A modern living room with a grey sectional sofa, a round coffee table, and a glass desk with a chair. Large windows offer a city view.

A spacious living area with a large sofa, a dining table, and a TV mounted on the wall.

Level Chicago – Old Town

Downtown Chicago

S$502

for 1 room

includes taxes & fees

A restaurant interior with brick walls, hanging spherical light fixtures, and a visible kitchen area.

A room with a diamond-patterned bookshelf filled with books, a wooden floor, and a lamp.

A bar area with multiple shelves of bottles, a bar counter, and three bar stools.

A modern living room with a brick wall mural, a green sofa, leather chairs, and a wooden coffee table.

Arlo Chicago

Downtown Chicago

S$764

for 1 room

includes taxes & fees

A historic building with a prominent casino sign, surrounded by modern skyscrapers.

A hotel room with two beds, a dining table with chairs, a city view, and a minibar.

A person pouring a drink into a glass with ice and an orange slice garnish.

A modern interior with a round table, four chairs, a vase with flowers, and a view of the street through large windows.

Hotel Felix River North/Magnificent Mile

Downtown Chicago

S$604

for 1 room

includes taxes & fees

Congress Plaza Hotel

Downtown Chicago

S$303

for 1 room

includes taxes & fees

Jaslin Hotel

Chinatown

S$250

for 1 room

includes taxes & fees

A swimming pool with a lifeguard station, chairs, and a clock on the wall.

A vending machine stocked with snacks and beverages, located in a corner of a room with wooden paneling.

A hotel lobby with a large dining table, several chairs, a small coffee table, and a fireplace.

Fairfield Inn and Suites by Marriott Chicago Midway Airport

Bedford Park

S$201

for 1 room

includes taxes & fees

A modern building with the name 'SENIORAL' prominently displayed on the facade.

A bar area with stools, a counter with bottles, and a wall with a leafy design.

A modern kitchen with a large island, bar stools, and a view of the city skyline.

A balcony with a glass railing, a table, and four chairs.

Sentral Michigan Avenue

Downtown Chicago

S$470

for 1 room

includes taxes & fees

The Chicago Hotel Collection - Magnificent Mile

Downtown Chicago

S$50 off

S$454

for 1 room

includes taxes & fees

Ohio House Motel

Downtown Chicago

S$390

for 1 room

includes taxes & fees

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Downtown Chicago

S$469

for 1 room

includes taxes & fees

An outdoor seating area with modern furniture, surrounded by tall buildings.

A hotel lobby with sofas, a reception desk, a staircase, and a view of the outside.

A modern kitchen with a central island, stainless steel appliances, and a view of the city.

Kasa Lake Shore Chicago

Downtown Chicago

S$45 off

S$438

for 1 room

includes taxes & fees

The Majestic Hotel

Lakeview

S$39 off

S$350

for 1 room

includes taxes & fees

A bar area with a long counter, bar stools, and a mirrored wall.

A luxurious lobby with a grand fireplace, elegant seating arrangements, and classic wood paneling.

A luxurious bathroom with a large oval bathtub, a chandelier, and two large mirrors with floral arrangements.

A restaurant with wooden flooring, long tables, and chairs with patterned upholstery.

The Whitehall Hotel, BW Premier Collection

Downtown Chicago

S$75 off

S$462

for 1 room

includes taxes & fees

The Willows Hotel

Lakeview

S$36 off

S$323

for 1 room

includes taxes & fees

A hallway with a bench, a door, and a wall-mounted light fixture.

A dining area with a fireplace, a wooden table, and chairs. There is a kitchen area with cabinets and appliances.

A reception area with a counter, a floral wall mural, and a door in the background.

A kitchen with a microwave, coffee makers, and a shelf with glassware and dishes.

City Suites Hotel

Lakeview

S$39 off

S$350

for 1 room

includes taxes & fees

Courtyard by Marriott Chicago Midway Airport

Bedford Park

S$309

for 1 room

includes taxes & fees

A bathroom with a glass-tiled wall, a sink, and a shower area.

A cozy interior with a wooden staircase, a seating area with chairs and a table, and shelves with various items.

A building with a large window, a bench, and a sign that reads "RAY'S BUCKTOWN BED & BREAKFAST".

A room with wooden flooring, a bookshelf filled with books and decorative items, two chairs, and a table with various objects.

Ray's Bucktown B&B

Bucktown

S$30 off

S$266

for 1 room

includes taxes & fees

The Chicago Hotel Collection River North

Downtown Chicago

S$33 off

S$293

for 1 room

includes taxes & fees

Sports Illustrated Resorts Chicago

Downtown Chicago

S$2,024

for 2 nights, 1 room

S$1,012 per night

includes taxes & fees

Courtyard by Marriott Chicago Midway Airport

Bedford Park

S$778

for 2 nights, 1 room

S$389 per night

includes taxes & fees

A multi-story hotel with a prominent sign reading "Crowne Plaza."

A modern restaurant with round tables and booths, a high ceiling with exposed beams, and a brick accent wall with the text "RVE DELTA".

A spacious lobby with a seating area, a reception desk, and a large screen.

A spacious lobby with high wooden pillars, a seating area with sofas and a bench, a fire feature, and a modern design.

Crowne Plaza Chicago West Loop by IHG

Downtown Chicago

S$1,700

for 2 nights, 1 room

S$850 per night

includes taxes & fees

A modern dining area with round tables and chairs, large windows, and a view of a cityscape.

A hotel room with a large bed, a chair, a window with a city view, and a bathroom area with a toilet and a sink.

A modern high-rise building with a curved glass facade, surrounded by other tall buildings.

A person in a white robe sitting by a window with a view of modern high-rise buildings.

Sofitel Chicago Magnificent Mile

Downtown Chicago

S$577 off

S$2,382

for 2 nights, 1 room

S$1,191 per night

includes taxes & fees

A modern bar area with a marble countertop, leather bar stools, a chandelier, and a wall-mounted TV.

A hotel lobby with a curved floor design, a glass entrance, and a large mural on the wall.

A modern lobby with a sofa, armchairs, and a table. A large window offers a view of the street.

A modern hotel with a glass facade, multiple floors, and a prominent entrance with a purple-lit canopy.

Ivy Boutique Hotel

Downtown Chicago

S$250 off

S$2,252

for 2 nights, 1 room

S$1,126 per night

includes taxes & fees

Hotel Felix River North/Magnificent Mile

Downtown Chicago

S$1,943

for 2 nights, 1 room

S$972 per night

includes taxes & fees

A modern hotel lobby with a sofa, coffee table, and a reception desk.

A hotel room with a bed, a TV on a wooden dresser, a window with a view of a cityscape, and a lamp on the nightstand.

A reception desk with a geometric wall art, a vase with flowers, and a digital screen displaying a mobile check-in message.

A hotel room with a sofa, a desk, a chair, a bed, a TV, and a large window offering a city view.

Renaissance Chicago O'Hare Suites Hotel

O'Hare

S$193 off

S$1,094

for 2 nights, 1 room

S$547 per night

includes taxes & fees

Freehand Chicago

Downtown Chicago

S$319 off

S$1,927

for 2 nights, 1 room

S$963 per night

includes taxes & fees

The Godfrey Hotel Chicago

Downtown Chicago

S$266 off

S$2,401

for 2 nights, 1 room

S$1,200 per night

includes taxes & fees

Eurostars Magnificent Mile

Downtown Chicago

S$2,464

for 2 nights, 1 room

S$1,232 per night

includes taxes & fees

A street view with a row of parked cars, a building with a sign reading "SONDE," and another sign that says "Diamonds On Parade."

A restaurant with outdoor seating and a sign for 'PIZANO'S PIZZA & PASTA'.

A neatly arranged hotel room with a large bed, a nightstand, a lamp, and a window with a view of buildings.

A modern kitchen with a dining area featuring two teal chairs, a round table, and a framed artwork on the wall.

LIVN - Millennium Park Downtown Chicago

Downtown Chicago

S$324 off

S$2,914

for 2 nights, 1 room

S$1,457 per night

includes taxes & fees

A cozy room with a sofa, a dining table, and a window with a view of buildings.

A modern hotel lobby with a dark wood console, a large mirror, and a view of the city through large windows.

A cozy seating area with a round table and two chairs, a brick wall, and a window with a view of buildings.

A lobby with two brown leather chairs, a marble table, and a large potted plant.

LIVN - West Loop Chicago

Downtown Chicago

S$281 off

S$2,532

for 2 nights, 1 room

S$1,266 per night

includes taxes & fees

Ohio House Motel

Downtown Chicago

S$130 off

S$2,034

for 2 nights, 1 room

S$1,017 per night

includes taxes & fees

A street view with outdoor seating, a building with a sign, and tall skyscrapers in the background.

A hotel entrance with a marquee sign, outdoor seating, and a well-lit facade.

A bar with three wooden shelves filled with bottles and glasses.

A lobby with a checkered floor, seating area, and a glass entrance.

The Talbott, Autograph Collection

Downtown Chicago

S$432 off

S$2,541

for 2 nights, 1 room

S$1,271 per night

includes taxes & fees

A modern kitchen with a stove, dishwasher, and a dining area with a round table and chairs.

A modern living room with a large window, a flat-screen TV, a grey armchair, a green sofa, and a small side table.

A modern building with a sign reading "TOUS les JOUS" and a tree with yellow leaves in front.

The Neighborhood Hotel-Little Italy

Near West Side

S$2,409

for 2 nights, 1 room

S$1,204 per night

includes taxes & fees

Check out pet-friendly hotels in Chicago

Hilton Chicago

Downtown Chicago

S$281

includes taxes & fees

24 Oct - 25 Oct

The Chicago Hotel Collection Ambassador Gold Coast

Downtown Chicago

S$272

includes taxes & fees

14 Oct - 15 Oct

A spacious room with a fireplace, a seating area with a sofa, a dining table with chairs, and a vending machine labeled "TREATS".

A hotel reception desk with a wooden finish and a large welcome sign above it.

A gym with treadmills, a bench, kettlebells, and weight machines.

A hotel room with two beds, a television, a desk, and a chair.

Hampton Inn by Hilton Chicago-Midway Airport

Bedford Park

S$213

includes taxes & fees

26 Oct - 27 Oct

The Claridge House building with a sign, American and another flag, and outdoor seating with umbrellas.

A modern kitchen with a central island, bar stools, a chandelier, and a large flat-screen TV.

A modern hotel room with a large bed, a chair, a small table, and a window with a view.

A bar area with a long counter, multiple stools, and a modern chandelier.

Claridge House Chicago, Tapestry Collection by Hilton

Downtown Chicago

S$260

includes taxes & fees

25 Oct - 26 Oct

A view through a glass door to an outdoor patio area with tables and chairs, a potted plant, and a clear sky.

A modern lounge area with a stone fireplace, comfortable seating, and artwork on the walls.

A snack kiosk with refrigerated display cases labeled 'SNACKS TO GO' and 'CHILL OUT.'

A modern hotel lobby with seating areas, a dining section, and a wall with a motivational quote.

Hampton Inn Chicago North-Loyola Station

Rogers Park

S$200

includes taxes & fees

28 Oct - 29 Oct

River Hotel

Downtown Chicago

S$282

includes taxes & fees

25 Oct - 26 Oct

A person pouring champagne into a glass near a window overlooking a cityscape with a Ferris wheel.

A rooftop terrace with a view of a beach and a Ferris wheel, featuring lounge chairs and a colorful mural.

A modern hotel lobby with a marble floor, seating areas, and a ceiling with a sky-like projection.

A modern hotel room with a large window offering a view of the sea and a cityscape. There is a seating area with a sofa and a small table.

The Wade

Downtown Chicago

S$226

includes taxes & fees

25 Oct - 26 Oct

Club Quarters Hotel, Central Loop, Chicago

Downtown Chicago

S$225

includes taxes & fees

25 Oct - 26 Oct

Fairfield Inn and Suites by Marriott Chicago Midway Airport

Bedford Park

S$169

includes taxes & fees

25 Oct - 26 Oct

Kasa Lake Shore Chicago

Downtown Chicago

S$348

includes taxes & fees

30 Sept - 1 Oct

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You can also stay at hotels with a pool in Chicago

Hilton Chicago

Downtown Chicago

S$281

includes taxes & fees

24 Oct - 25 Oct

The Wade

Downtown Chicago

S$226

includes taxes & fees

25 Oct - 26 Oct

A multi-story building with a Starbucks Coffee on the ground floor, emergency exit signs, and a Hyatt Center sign.

An indoor swimming pool with lounge chairs and exercise equipment.

A modern workspace with two Apple iMacs, a desk with a keyboard, and a bookshelf filled with books and decorative items.

A bar area with a modern design, featuring a long counter and multiple seating options.

Hyatt Centric Chicago Magnificent Mile

Downtown Chicago

S$416

includes taxes & fees

1 Oct - 2 Oct

A modern hotel with a glass facade, multiple floors, and a prominent sign.

A person pouring a drink from a tap into a glass.

An outdoor rooftop lounge with seating, planters, and a view of surrounding high-rise buildings.

A modern dining area with a central island, chairs, pendant lights, and a decorative wall with a motivational quote.

Hampton Inn Chicago West Loop Fulton Market Area

Downtown Chicago

S$345

includes taxes & fees

25 Oct - 26 Oct

A modern lobby with a grey sofa, checkered ottomans, and a coffee table. There are black chairs, a blue sofa, and a TV on a stand.

A modern indoor swimming pool with blue seating and a view of the city through large windows.

A modern high-rise hotel with multiple floors, large windows, and a well-lit entrance area.

A modern hotel room with a bed, a sofa, a coffee table with flowers, a TV, and a large window with a city view.

Aloft by Marriott Chicago Mag Mile

Downtown Chicago

S$330

includes taxes & fees

25 Oct - 26 Oct

A hotel room with a large window offering a city view, a bed, a desk, and a chair.

A reception area with a modern design, featuring a large window, a reception desk, and artwork on the wall.

A bar area with a granite countertop, bar stools, and a variety of bottles and glasses.

Courtyard by Marriott Chicago Magnificent Mile

Downtown Chicago

S$326

includes taxes & fees

25 Oct - 26 Oct

A breakfast setting with a plate of toast, a bowl of fruit, a cup of coffee, and a newspaper on a table by a window with a city view.

A modern interior with a bar area, seating, and large windows offering a city view.

A bar area with a circular bar, stools, and a well-stocked shelf of bottles.

A building facade with a dark entrance, two wall-mounted lights, and a sign reading "The Robey Chicago".

The Robey, Chicago, a Member of Design Hotels

West Town

S$363

includes taxes & fees

25 Oct - 26 Oct

A modern hotel with a glass facade, multiple floors, and a visible entrance.

A gym with cardio machines, weight benches, and a large window offering a city view.

A reception area with a modern design, including a reception desk, a decorative wall, and a display case with snacks.

A modern hotel room with a large window, a desk with a lamp, a sofa, and a chair.

Hyatt Place Chicago/Downtown - The Loop

Downtown Chicago

S$322

includes taxes & fees

25 Oct - 26 Oct

A swimming pool with lounge chairs and umbrellas, surrounded by tall buildings.

Transparent igloo-like structures with seating inside, set on a wooden deck with snow on the ground, surrounded by tall buildings.

A modern lobby with a seating area, a bar, and a green wall.

A cozy room with a patterned carpet, a wooden table, and a green sofa with a white throw blanket.

DoubleTree by Hilton Chicago - Magnificent Mile

Downtown Chicago

S$296

includes taxes & fees

25 Oct - 26 Oct

A rooftop terrace with lounge chairs and tables, offering a city skyline view.

A hotel room with a large bed, two armchairs, a wooden dresser, a desk with a chair, a flat-screen TV, and framed pictures on the wall.

A modern bar area with a stainless steel bar counter, multiple stools, a refrigerated display, and a large window offering a view of the city.

A hotel lobby with a reception desk, seating area, and a view of the city.

Best Western River North Hotel

Downtown Chicago

S$244

includes taxes & fees

25 Oct - 26 Oct

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Go beyond your typical stay in Chicago

Our prices for hotels in Chicago are cheapest in February

Top neighbourhoods in Chicago

A river with yellow boats, a bridge, and tall buildings.

A nighttime cityscape with illuminated buildings and a bridge over a river.

A nighttime cityscape with illuminated skyscrapers and a river.

A river with a bridge, modern buildings, and a historic tower.

A river with a yellow boat and a white yacht. In the background, there are tall buildings and a bridge.

The Loop

The Loop electrifies with skyscraper energy and cultural powerhouses that'll make your neck hurt from looking up. Snap selfies with "The Bean" in Millennium Park or lose track of time at the Art Institute's world-class art collection. The Chicago Symphony Orchestra delivers spine-tingling performances while the rumbling "L" trains create the neighborhood's signature urban soundtrack. Getting around couldn't be easier with multiple train and metro stations connecting you to everywhere worth going. Dining options range from quick lunch spots to upscale steakhouses catering to the business crowd. Hotels tend towards the luxurious side, perfect for travellers who appreciate city centre convenience with a side of architectural wow-factor.

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A large, historic building with a central tower and multiple windows, located near a body of water.

A city street with a train passing overhead, cars, pedestrians, and a red brick building.

A nighttime cityscape with illuminated buildings, a river, and a bridge.

A modern building with illuminated signage, surrounded by urban skyscrapers and a curved road with light trails.

A coastal cityscape with a long beach, dense urban buildings, and a clear blue sea.

River North

River North buzzes with Chicago's most vibrant nightlife and foodie scene. Art lovers can explore America's largest gallery concentration outside Manhattan, with everything from contemporary pieces to photography exhibits. The Chicago River offers scenic strolls while Merchandise Mart and swanky shops keep retail therapy within reach. You won't lack things to do in this playground for grown-ups. Upscale hotels and boutique properties dominate the accommodation scene, many with rooftop bars and river views. Getting around is a breeze with three metro stations (Merchandise Mart, Chicago, and Grand) connecting you to the whole city. The neighborhood's grid layout makes walking a pleasure despite the bustling crowds.

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A busy urban street at dusk with tall buildings, a historic tower, and pedestrians.

A city intersection with tall buildings, including a historic building labeled "Water Tower Place."

A cityscape with tall buildings, including a historic tower and modern skyscrapers.

A historic building with a fountain in the foreground.

A cityscape at night with illuminated buildings, a large Christmas tree, and a statue.

Magnificent Mile

Magnificent Mile dazzles with its canyon of glitzy skyscrapers and luxury flagship stores that make window shopping an Olympic sport. The historic Water Tower stands proudly among modern retail palaces, while Chicago's stunning riverfront beckons just steps away. From rooftop cocktail lounges to celebrity chef restaurants, this stretch delivers big-city energy with a side of architectural wonder. Getting around couldn't be easier with frequent buses, nearby train stations, and super-walkable wide pavements. High-end hotels dominate the accommodation scene, putting you right in the heart of Chicago's shopping paradise. Expect a polished, international atmosphere where tourists and business travellers mingle amid the retail magic.

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A cityscape with modern skyscrapers and a curved highway.

A cityscape with a mix of modern and older buildings, including a prominent red building with many windows and balconies.

A cityscape with a mix of modern and older buildings, a busy highway, and a large parking lot.

A city skyline with modern skyscrapers, a parking lot, and a distinctive building with a geometric facade.

A cityscape with a prominent skyscraper, a dense urban area, and a clear sky.

West Loop

West Loop has transformed from an industrial zone into Chicago's culinary playground. Former warehouses now house art galleries and design studios, while "Restaurant Row" sizzles with celebrity chef hotspots and craft breweries. Visitors can explore converted lofts, browse boutique shops, or relax in Mary Bartelme Park between food adventures. Getting around is a breeze with three transit stations including Racine and Clinton on the Green Line. Most attractions sit within easy walking distance along wide pavements and bike lanes. Accommodation options feature industrial-chic hotels with exposed brick and modern amenities, perfectly matching the neighborhood's creative energy.

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A river with a city skyline in the background, surrounded by green trees and grass.

A city skyline with a river, green spaces, and a baseball field.

A city skyline with tall buildings, a frozen lake, and leafless trees in a park.

A city skyline with high-rise buildings, a calm river reflecting the structures, and a park with trees and a walking path.

Lincoln Park

Lincoln Park is where Chicago shows off its outdoorsy side with a splash of sophistication. The 1,200-acre park offers everything from a free zoo with 1,000 animals to serene lily pools and a tropical plant conservatory. Locals and visitors alike hit the lakefront trails for morning jogs or grab a volleyball game at North Avenue Beach. Tree-lined streets with gorgeous brownstones give you that authentic Chicago area feel. Restaurants range from upscale bistros to trendy gastropubs, with most spots requiring dinner reservations. Getting around couldn't be easier with three metro stations and plenty of bus routes criss-crossing the area. Shop the boutiques along Armitage Avenue or catch live performances at nearby theatres for the full Lincoln Park experience.

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Top landmarks in Chicago

An aerial view of a baseball stadium surrounded by urban buildings.

Wrigley Field

9.0/10 (11,704 reviews)

Why not catch an event at Wrigley Field, a major stadium in Lakeview. Let yourself be amazed at the art galleries in the area – your cultural tour starts here. If you think Wrigley Field is cool, you might also like United Center and Aragon Ballroom, both located nearby.

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A modern glass building with a curved roof, surrounded by a landscaped garden and a water feature.

McCormick Place

8.8/10 (9,822 reviews)

McCormick Place is worth a pic or two when discovering Near South Side. Hotels.com travellers also like the art galleries, museums and monuments in the area.

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A large stadium surrounded by a cityscape with modern buildings.

Soldier Field

8.8/10 (7,063 reviews)

Imagine soaking up the atmosphere at Soldier Field, a major stadium in Near South Side. Hotels.com travellers also like the art galleries, museums and monuments in the area. If you think Soldier Field is cool, you might also like United Center and Wintrust Arena, both located nearby.

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A Ferris wheel and a carousel at a fairground.

Navy Pier

9.0/10 (24,140 reviews)

If you want to give your credit card some exercise, head out to Navy Pier, a popular place for shoppers in Downtown Chicago. Why not take a stroll along the riverfront and watch the sunset while you're here?

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A large metallic sphere sculpture in a public square surrounded by tall buildings.

Millennium Park

9.4/10 (30,446 reviews)

Millennium Park is worth a pic or two when discovering Downtown Chicago. Why not take a stroll along the riverfront and watch the sunset while you're here?

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A cityscape at night with illuminated buildings, a river, and a bridge.

Chicago Riverwalk

9.6/10 (13,574 reviews)

Chicago Riverwalk is worth a pic or two when discovering Downtown Chicago. Why not take a stroll along the riverfront and watch the sunset while you're here?

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A city street at night with illuminated buildings, a snow-covered sidewalk, and light trails from moving vehicles.

Michigan Avenue

9.4/10 (15,813 reviews)

If you want to give your credit card some exercise, head out to Michigan Avenue, a popular place for shoppers in Downtown Chicago. Why not take a stroll along the riverfront and watch the sunset while you're here? It's also full of great shops and restaurants, so you can spend the afternoon having a wander. Splash some more cash at Shops at North Bridge, Water Tower Place and 900 North Michigan Shops.

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A large, modern building with a curved facade and multiple vertical windows.

United Center

8.8/10 (4,269 reviews)

Why not catch an event at United Center, a major stadium in Near West Side. Let yourself be amazed at the museums and art galleries in the area too. If you think United Center is cool, you might also like Soldier Field and Wrigley Field, both located nearby.

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Chicago and related destinations

Towering skyscrapers create a skyline that seems to rise straight from Lake Michigan's blue waters. The Art Institute houses masterpieces while Millennium Park's reflective 'Bean' sculpture distorts the city in delightful ways. Navy Pier offers carnival-like fun with a giant Ferris wheel providing spectacular views. Wrigley Field remains gloriously old-school, where ivy-covered walls and hand-turned scoreboards transport baseball fans to another era. Deep-dish pizza at local institutions sparks fierce debates about whose crust reigns supreme. The Chicago River's architecture boat tours reveal how the city rebuilt itself after the Great Fire. Field Museum's Sue, the world's most complete T-Rex, stares down visitors with 65-million-year-old intensity.

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Check out reviews of Chicago hotels guests love

A restaurant with booths and tables, a television on the wall, and a view of the street outside.

A modern hotel lobby with a long blue sofa, numbered cushions, and hanging planters.

A bar area with a long counter, multiple liquor bottles, and a variety of glasses.

Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

10/10 Exceptional

Rahul

L7 Chicago by LOTTE

Downtown Chicago

10/10 Exceptional

Sungwon

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

10/10 Exceptional

Nora Emma Oribello

A hotel lobby with a bar area, a chandelier, and a reception desk.

A hotel lobby with leather seating, a flat-screen TV, and large windows with a view of the cityscape.

A high-rise building with a clock tower, large windows, and a busy street with vehicles.

A view through a circular window of a cityscape with modern buildings and a body of water in the distance.

Residence Inn Chicago Downtown/Loop

Downtown Chicago

10/10 Exceptional

Francis

Frequently Asked Questions

Can I book a refundable accommodation option in Chicago?

If you want the flexibility to change your plans to Chicago, most hotels offer refundable* rates that you can book. You can find these properties by searching our site and using the "fully refundable" filter to narrow down the results.

Where can I stay in Chicago if I want a holiday rental instead of a hotel?

If you want a good alternative to a hotel, look over our selection of 426 holiday homes. In addition, there are 1942 apartments and 236 condos.

What will the weather in Chicago be like during my visit?

July and August are typically the warmest months in Chicago, when the average temperature is 21°C. January and February are the coldest months, when the average temperature is -1°C. June and May are the months with the most rain.

Why should I book my Chicago hotel with Hotels.com?

There are lots of reasons to book your Chicago trip with us: our free cancellations on selected hotels* gives you flexibility, our Price Guarantee ensures that you always get the lowest price, and you can earn rewards on every booking.

Find out more about Chicago

Chicago: A Tapestry of Skyscrapers, Culture and Riverfront Wonders

Chicago, the Windy City, is a captivating urban destination renowned for its stunning skyline and rich cultural tapestry. Marvel at architectural wonders such as the Willis Tower and the historic Chicago Riverwalk, where you can take leisurely strolls along the water. Delve into the city’s vibrant arts scene at the Art Institute of Chicago and enjoy the lush greenery of Millennium Park. Indulge in the culinary delight of deep-dish pizza and immerse yourself in the lively jazz and blues heritage. With a blend of iconic landmarks and diverse neighbourhoods, Chicago promises an unforgettable experience for every traveller.

Discover great hotels near Chicago

Chicago offers a diverse range of hotel accommodations, from luxury high-rises with stunning skyline views to charming boutique hotels in historic districts. Many options are conveniently located near major attractions, restaurants, and public transport, making it easy to explore the city's vibrant culture and rich history. Here are some of the best hotels near Chicago that our travelers love:

The Shamrockopens in new window: This budget-friendly motel provides a comfortable stay with essential amenities that cater to the needs of leisure travellers. Enjoy entertainment options like various television formats and streaming services, ensuring you can unwind after a day of exploration. The property is conveniently located near a variety of attractions, making it easy to discover the surrounding area. Review sentiments highlight the cleanliness of the rooms, adding to the overall positive experience for guests seeking simplicity and value during their travels.
Harvey House Bed & Breakfastopens in new window: This elegant 4.0-star hotel exudes charm, offering a remarkable experience for discerning travellers. With a guest rating of 9.8, it features a delightful breakfast service and a snack bar to keep you refreshed throughout the day. The property is well-connected, making it an ideal base for those looking to explore the vibrant city. Guests rave about the spotless rooms and the warm, welcoming atmosphere, ensuring a memorable stay focused on comfort and convenience.
Carleton of Oak Parkopens in new window: This boutique 3.0-star hotel is a perfect choice for leisure travellers looking for a unique and artistic lodging experience. With a guest rating of 9.2, the property showcases distinctive decor that sets it apart from typical hotel offerings. The atmosphere here is charming and inviting, making it an excellent retreat after a day of sightseeing. Positive sentiments from reviews highlight the cleanliness and the overall value, ensuring that guests enjoy a stylish and comfortable stay in a thoughtfully designed environment.

Where to stay in Chicago

Stay in Elmwood Park, Magnificent Mile, or The Loop when visiting Chicago. Elmwood Park offers a family-friendly atmosphere with dining and wildlife experiences. The Magnificent Mile dazzles with skyscrapers, shopping, and scenic views along the river. The Loop is a cultural hub, rich in art and entertainment. For first-time visitors, the Magnificent Mile is ideal for its vibrant urban experience.

Magnificent Mileopens in new window: The Magnificent Mile is a vibrant area in Chicago that offers an exciting blend of urban charm and architectural beauty. Known for its stunning skyscrapers and lively atmosphere, this iconic stretch along Michigan Avenue is perfect for shoppers and culture enthusiasts alike. You can explore an array of high-end shops, enjoy delightful dining options, and take in scenic views of the Chicago River and Lake Michigan. Key attractions include the Navy Pier, a bustling hub for entertainment and events, and Grant Park, a beautiful green space that hosts numerous festivals. Staying here means you’re in the heart of the city, where everything is just a short walk away.
The Loopopens in new window: The Loop is Chicago's bustling business district and a cultural hotspot with a unique blend of historic and modern architecture. It's an excellent choice for those who appreciate art and theatre, as this area is home to several museums and cultural institutions. Explore famous sites like Millennium Park, where you can see the iconic Cloud Gate sculpture, or catch a show at one of the many theatres nearby. The Loop also offers a variety of shopping and dining options, making it easy to enjoy the city's local flavours. With its convenient public transport connections, The Loop provides easy access to the rest of Chicago.
Elmwood Parkopens in new window: Elmwood Park is a charming, family-friendly suburb that offers a quieter escape from the hustle and bustle of downtown Chicago. With its lush parks and green spaces, it's a great place for birdwatching and enjoying nature. The area has a nice range of dining options that cater to families, along with some local shopping spots. Elmwood Park's relaxed vibe is perfect for those seeking a more laid-back stay while still being close to the city’s attractions. The community's welcoming atmosphere makes it an ideal destination for family gatherings and leisurely strolls.

Things to do in Chicago

Chicago is a vibrant metropolis where stunning skyscrapers rise alongside serene lakes and lush parks. Stroll along the scenic riverwalk, indulge in theatre performances, and explore dynamic art scenes. With beaches for sunbathing and inviting green spaces for picnics, it's a delightful blend of urban energy and natural beauty.

The 606opens in new window – The 606 is a esplanade that offers a pleasant walk among modern skyscrapers and interesting architecture. Enjoy a stroll along this elevated route and take in the mix of museums, monuments and the nearby river views that create a vivid urban tapestry.
Griffin Museum of Science and Industryopens in new window – At the Griffin Museum of Science and Industry, you can delve into a world of scientific discovery. The museum’s engaging exhibits are set against a backdrop of striking architecture, with nearby skyscrapers and monuments adding to the appeal of this landmark location.
Jackson Parkopens in new window – Jackson Park presents a charming urbanPark experience where you can relax and explore well-maintained green spaces. The park is surrounded by impressive skyscrapers and notable monuments, making it a pleasant spot to enjoy a leisurely walk while absorbing the urban landscape.
Field Museum of Natural Historyopens in new window – The Field Museum of Natural History invites you to explore fascinating exhibits that showcase the natural world. This iconic naturalHistoryMuseum is set among towering architecture and is close to remarkable monuments, offering a blend of education and scenic views near the river.
Michigan Avenueopens in new window – Michigan Avenue is a vibrant street where the city’s architectural splendour comes to life. As you wander along this bustling thoroughfare, you will encounter an array of iconic skyscrapers and monuments, with several museums adding cultural richness to your urban journey.

4 tips for savvy savings when booking a hotel in Chicago

Book for the cheapest times: The most affordable time to visit Chicago is during January, February, and December, when hotel prices tend to be lower. For those on a budget, a stay of at least 2 to 3 days is recommended to fully appreciate the city's iconic landmarks and rich cultural heritage. Visitors can explore stunning skyscrapers, remarkable architecture, and a variety of theatres and museums, as well as vibrant art scenes and scenic river views. This timeframe offers great value for money, allowing you to immerse yourself in Chicago's historical and cultural attractions while keeping expenses manageable.
Look for last-minute deals on Hotels.com: To uncover last-minute deals to Chicago on Hotels.com, begin by exploring the Dealsopens in new window or Last-Minute Deals sections, where you may discover discounted hotel options as your travel date approaches. Additionally, enabling email alerts or push notifications will help you stay informed about flash sales and special promotions. With the Smart Shopping tool available via the app, you could find it easier to compare hotel prices and amenities, ensuring you're the first to know if rooms become available or if prices drop, allowing you to seize any opportunities for a spontaneous getaway.
Be flexible with dates: Prices may fluctuate due to various factors, including the hotel's location, star rating, and the time of year. Therefore, being flexible with your travel dates could help you find a more economical option for your stay in a Chicago hotel. If you're in search of something a bit different, boutique hotels often provide a more personalised experience and may offer better value. When you book through Hotels.com, we will inform you whether the price for your chosen dates is above or below the average. If the price appears to be on the higher side, we will suggest alternative dates that could potentially offer you a more appealing rate.
Consider your location: Hotels situated near the city centre generally tend to be more expensive, but thanks to Chicago's superb public transport system, you may discover a more affordable independent hotel located further out that remains well connected. For those keen to explore alternative, less crowded neighbourhoods or even lesser-known nearby towns, there is often excellent value for money to be found. Opting for these alternative destinations could provide a more authentic and budget-friendly experience.

Best time to go to Chicago

Chicago experiences its lowest average temperature in January, at 25.7°F (-3.5°C), while July is the hottest month, with an average temperature of 73.4°F (23.0°C). June is typically the wettest month. If you’re looking to soak up the lively atmosphere in Chicago, April, June, and July are the peak months to visit, bustling with fellow travelers. During this peak period, the weather is mostly sunny, with light rainfall. However, if you prefer a more relaxed experience, October to December are perfect for a quieter getaway, marked by light rainfall and mostly sunny to mostly cloudy conditions.