An airplane exhibit labeled "Concourse A" in an airport terminal.

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Check availability on Southwest Side Luxury Hotels

Tonight
29 Sept - 30 Sept
Tomorrow
30 Sept - 1 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

Our top choices for Southwest Side luxury hotels

An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.
A spacious outdoor dining area with large windows overlooking the sea, featuring multiple tables and stools.
A modern living room with a large window overlooking a body of water, a tripod, and a sofa.
A view from a room with a large window overlooking a cityscape at night, featuring a river and illuminated buildings.

1. Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
S$457
includes taxes & fees
29 Oct - 30 Oct
Sable at Navy Pier Chicago, Curio Collection by Hilton
A large, historic building with a central courtyard surrounded by trees.
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.
A marina with numerous boats docked, surrounded by a cityscape with high-rise buildings and a stadium.

2. Hilton Chicago

Hilton Chicago
Downtown Chicago
S$289
includes taxes & fees
30 Oct - 31 Oct
Hilton Chicago
A spacious bar area with high ceilings and large windows, offering views of a cityscape.
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.
A cityscape with modern high-rise buildings, a river, and a boat.

3. Hyatt Regency Chicago

Hyatt Regency Chicago
Downtown Chicago
S$407
includes taxes & fees
31 Oct - 1 Nov
Hyatt Regency Chicago
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 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 restaurant with high ceilings, wooden flooring, and a central chandelier. Tables are set with wine glasses and red cushions.
A modern hotel lobby with leather sofas, a coffee table, and a floor lamp.

4. L7 Chicago by LOTTE

L7 Chicago by LOTTE
Downtown Chicago
S$377
includes taxes & fees
31 Oct - 1 Nov
L7 Chicago by LOTTE
A modern reception area with a marble reception desk, a sofa, armchairs, and a coffee table.
A luxurious hotel lobby with marble columns, a polished floor, and ornate chandeliers.
A couple in white robes sitting in a bathtub with candles and a bottle of champagne.
A grand hotel lobby with a high ceiling, a large chandelier, and a staircase leading to an upper floor.

5. JW Marriott Chicago

JW Marriott Chicago
Downtown Chicago
  • Spa indulgence awaits in city centre Chicago where luxurious treatments and premium dining create memorable moments.
S$431
includes taxes & fees
30 Oct - 31 Oct
JW Marriott Chicago
An outdoor seating area with a glass table, orange cushions, and potted plants.
A modern living room with a fireplace, large windows, and a flat-screen TV mounted on the wall.
A modern building with a large glass facade and a river in front.
A modern hotel lobby with a bar area, seating arrangements, and decorative lighting.

6. Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk
Downtown Chicago
S$409
includes taxes & fees
31 Oct - 1 Nov
Sheraton Grand Chicago Riverwalk
A high-rise hotel with a prominent Marriott sign, surrounded by other tall buildings and a busy street.
A hotel room with a large bed, a desk, a chair, and a TV. There are large windows with curtains, and a city view.
A modern bar area with a central island, bar stools, and a television screen displaying a news program.
A modern gym with treadmills, weight machines, and a curved ceiling.

7. Chicago Marriott Downtown Magnificent Mile

Chicago Marriott Downtown Magnificent Mile
Downtown Chicago
S$416
includes taxes & fees
31 Oct - 1 Nov
Chicago Marriott Downtown Magnificent Mile
A modern kitchen with a marble island, fruit bowls, and a city view.
A modern lounge area with a central bar, seating arrangements, and a decorative chandelier.
A Fairmont hotel with a prominent entrance, large windows, and a sculpture on the facade.
A modern hotel room with a city view, a seating area with two sofas and a coffee table, and a dining area with a table and chairs.

8. Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park
Downtown Chicago
S$303
includes taxes & fees
31 Oct - 1 Nov
Fairmont Chicago at Millennium Park
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 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.
A modern bar area with high stools, a bar counter, and shelves of liquor bottles.

9. The Wade

The Wade
Downtown Chicago
  • Luxurious lakeside retreat in city centre Chicago offers pillowtop beds, designer toiletries, and stunning views near Michigan Avenue.
S$226
includes taxes & fees
25 Oct - 26 Oct
The Wade
An outdoor seating area with tables and chairs, surrounded by city buildings and a view of the urban skyline.
A bar area with a long counter, metal bar stools, hanging pendant lights, and a variety of bottles on shelves.
A modern interior with a spacious layout, a large window offering a city view, and a variety of seating options.
An indoor swimming pool with a skylight, lounge chairs, and potted plants.

10. Renaissance Chicago Downtown Hotel

Renaissance Chicago Downtown Hotel
Downtown Chicago
S$522
includes taxes & fees
31 Oct - 1 Nov
Renaissance Chicago Downtown Hotel
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Top Southwest Side Hotel Reviews

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent
"Muy bueno todo . Excelente ubicaciรณn"
Julio 4-night trip
Posted 1 hour ago
The Chicago Hotel Collection - Magnificent Mile
River Hotel

River Hotel

8/10 Good
"The rooms were clean and beds were comfortable. The staff were very helpful and friendly"
Richard 2-night trip
Posted 2 hours ago
River Hotel
L7 Chicago by LOTTE

L7 Chicago by LOTTE

8/10 Good
"Nice bed in our king room. Location was perfect for us for all we had planned and coming in the CTA from midway . Disappointed no bar just the one next door at the restaurant that wasnโ€™t open late at all . We flew in very early in morning hoped to get into a room early even if we had to pay extra but the check in person was no help at all in regards to check in early or any of our questions . Our family came in the next morning same time and this time a different check in person actually offered them to check in early ! We had nowhere to go so we walked a lot of the city waiting to check in . I think we walked 13 miles . Our room ,once we got it ,was nice tho we didnโ€™t get the city view just the view across to a building and parking . Location was definitely the highlight of this hotel ."
sandra 2-night trip
Posted 2 hours ago
L7 Chicago by LOTTE
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

10/10 Excellent
"Great"
justin 3-night trip
Posted 2 hours ago
The Royal Sonesta Chicago Downtown
Central Loop Hotel

Central Loop Hotel

10/10 Excellent
"Clean room"
Gordon 1-night trip
Posted 3 hours ago
Central Loop Hotel
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

10/10 Excellent
"The only improvement would be lighting above the desk."
Kevin 1-night trip
Posted 4 hours ago
Club Quarters Hotel, Central Loop, Chicago
Hilton Chicago

Hilton Chicago

10/10 Excellent
"Very good stay the hotel was clean and the bed was comfortable, close to all the good spots as well. Iโ€™d stay here again in the future"
Gordon 2-night trip
Posted 6 hours ago
Hilton Chicago
Hampton Inn Chicago Downtown/Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile

10/10 Excellent
"Traveling cross country and stayed at several hotel. This one was on point, from entering the hotel, smelling clean, the staff checking in was great, and the room was clean. I had an awesome stay."
Jose 2-night trip
Posted 7 hours ago
Hampton Inn Chicago Downtown/Magnificent Mile
The Wade

The Wade

10/10 Excellent
"Everything great and everyone e great"
Holly 4-night trip
Posted 8 hours ago
The Wade

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