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Compare and book 5 Star hotels in Far Southwest Side, Chicago

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Check availability on Far Southwest Side 5 Star Hotels

Tonight
24 Aug - 25 Aug
Tomorrow
25 Aug - 26 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sept - 6 Sept

Our top choices for Far Southwest Side 5-star hotels

A person sitting by a window with a view of a cityscape, including a tall tower.
A modern bar area with a central bar and multiple stools, surrounded by a high ceiling with a decorative light fixture.
A couple walking through a spacious lobby with marble flooring, large white floral arrangements, and a modern staircase in the background.
An indoor swimming pool with a skylight, a lifeguard chair, and a potted plant.

1. Four Seasons Hotel Chicago

Four Seasons Hotel Chicago
Downtown Chicago
United States
August
£484
includes taxes & fees
7 Sept - 8 Sept
Four Seasons Hotel Chicago
A cityscape with a river, a bridge, and a dining area with tables and chairs.
A modern hotel room with large windows, white furniture, and a view of tall buildings.
A high-rise hotel with a prominent 'TRUMP' sign, reflecting in the water, surrounded by other tall buildings.
A pool area with a view of a cityscape, a lounge with wicker furniture, and a person relaxing in the pool.

2. Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago
Downtown Chicago
United States
Jorge
£408
includes taxes & fees
31 Aug - 1 Sept
Trump International Hotel & Tower Chicago
A modern hotel lobby with a reception desk, seating area, and large windows offering city views.
A modern hotel room with a large window offering a city view, three armchairs arranged around a central coffee table, and a decorative hanging plant.
A swimming pool with a ceiling of lights, large windows, and potted plants.
A spacious lobby with a modern sofa, armchairs, and a coffee table. A large window offers a view of the cityscape.

3. The Langham, Chicago

The Langham, Chicago
Downtown Chicago
United States
Dolores
£491
includes taxes & fees
7 Sept - 8 Sept
The Langham, Chicago
A high-rise hotel with multiple floors, large windows, and a prominent Tiffany & Co. store on the ground level.
A rooftop bar with seating and a view of the city skyline at night.
A spacious hotel lobby with multiple seating areas, a grand staircase, and large windows offering views of the city.
A modern indoor pool area with large windows, potted palm plants, and lounge chairs.

4. The Peninsula Chicago

The Peninsula Chicago
Downtown Chicago
United States
Justin
£532
includes taxes & fees
30 Aug - 31 Aug
The Peninsula Chicago
A black luxury car parked in front of a hotel entrance with a glass canopy decorated with festive ornaments.
A bar area with a long counter, multiple stools, and a seating area with a booth.
A couple dining on a balcony with a cityscape view.
A bar area with a polished marble floor, bar stools, a counter with bottles, and a decorative lamp.

5. Waldorf Astoria Chicago

Waldorf Astoria Chicago
Downtown Chicago
United States
Jim
£500
includes taxes & fees
31 Aug - 1 Sept
Waldorf Astoria Chicago
A modern indoor space with a glass ceiling, marble flooring, and contemporary furniture.
A spacious lobby with a central seating area, a reception desk, and a large chandelier.
A modern lobby with a central seating area, large windows, and a decorative ceiling feature.
A modern bar area with a central bar, multiple seating options, and a large chandelier.

6. The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago
Downtown Chicago
United States
Eric
£518
includes taxes & fees
30 Aug - 31 Aug
The Ritz-Carlton, Chicago
A modern indoor swimming pool with a clear blue water surface, a wooden ceiling, and a wall with a floral pattern.
A modern hotel room with a large window offering a city view, a wooden desk with a laptop, and a small seating area.
A rooftop terrace with a view of a city skyline at dusk.
A modern lobby with a sofa, a coffee table, and a vase of flowers.

7. Nobu Hotel Chicago

Nobu Hotel Chicago
Downtown Chicago
Canada
Jordan
£400
includes taxes & fees
7 Sept - 8 Sept
Nobu Hotel Chicago
A couple dining at a table with a view of a cityscape and a sunset.
A woman sitting by a window with a city view, holding a cup and saucer.
A rooftop terrace with a dining table, chairs, and a view of the cityscape, including the Water Tower Place building.
A modern living room with a sofa, chairs, a coffee table, and a TV. A large window offers a view of a cityscape and a tower.

8. Park Hyatt Chicago

Park Hyatt Chicago
Downtown Chicago
United States
Jennifer
£482
includes taxes & fees
30 Aug - 31 Aug
Park Hyatt Chicago
A restaurant with tables and chairs arranged in a corridor, large windows, and hanging lamps.
A modern hotel entrance with a prominent "STREGIS" sign, large glass windows, and a well-lit facade.
A rooftop pool area with city views, two lounge chairs, and a small table with a vase.
A modern hotel lobby with a large seating area, a view of the city, and a green accent wall.

9. The St. Regis Chicago

The St. Regis Chicago
Downtown Chicago
United States
Princess
£545
includes taxes & fees
7 Sept - 8 Sept
The St. Regis Chicago
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Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Far Southwest Side.
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includes taxes & fees
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includes taxes & fees
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The Chicago Hotel Collection Ambassador Gold Coast

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1 Sept - 2 Sept
includes taxes & fees
8/10 Very good! (2,084 reviews)
The Chicago Hotel Collection Ambassador Gold Coast
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