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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
10 Oct - 11 Oct
Tomorrow
11 Oct - 12 Oct
Next weekend
16 Oct - 18 Oct
In two weeks
23 Oct - 25 Oct

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 couple walking through a spacious lobby with marble flooring, large white floral arrangements, and a modern staircase in the background.
A group of people on a boat with a city skyline in the background.
A modern bar area with a central bar and multiple stools, surrounded by a high ceiling with a decorative light fixture.

1. Four Seasons Hotel Chicago

Four Seasons Hotel Chicago
Downtown Chicago
United States
Edda
£467
includes taxes & fees
1 Nov - 2 Nov
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 pool area with a view of a cityscape, a lounge with wicker furniture, and a person relaxing in the pool.
A high-rise hotel with a prominent 'TRUMP' sign, reflecting in the water, surrounded by other tall buildings.

2. Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago
Downtown Chicago
United States
Cecille
£415
includes taxes & fees
1 Nov - 2 Nov
Trump International Hotel & Tower Chicago
A modern hotel lobby with a reception desk, seating area, and large windows offering city views.
A modern dining area with round tables, comfortable chairs, and a dessert display.
A spacious lobby with a modern sofa, armchairs, and a coffee table. A large window offers a view of the cityscape.
A swimming pool with a ceiling of lights, large windows, and potted plants.

3. The Langham, Chicago

The Langham, Chicago
Downtown Chicago
United States
Saramae
£469
includes taxes & fees
1 Nov - 2 Nov
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 bar area with a checkered floor, bar stools, and a bartender.

4. The Peninsula Chicago

The Peninsula Chicago
Downtown Chicago
United States
Levi
£562
includes taxes & fees
1 Nov - 2 Nov
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 polished marble floor, bar stools, a counter with bottles, and a decorative lamp.
A couple dining on a balcony with a cityscape view.
An indoor swimming pool with a modern design, a reception area with a sign for Waldorf Astoria Chicago, and a seating area with two people.

5. Waldorf Astoria Chicago

Waldorf Astoria Chicago
Downtown Chicago
United States
Luis
£486
includes taxes & fees
1 Nov - 2 Nov
Waldorf Astoria Chicago
A spacious dining area with high ceilings, large windows, and a modern chandelier.
A rooftop terrace with a view of a city skyline at dusk.
A modern hotel room with a large window, a wooden desk, a bathroom with a mirror, and a view of the cityscape.
A modern indoor swimming pool with a clear blue water surface, a wooden ceiling, and a wall with a floral pattern.

6. Nobu Hotel Chicago

Nobu Hotel Chicago
Downtown Chicago
United States
Abhay
£428
includes taxes & fees
1 Nov - 2 Nov
Nobu Hotel Chicago
A couple dining at a table with a view of a cityscape and a sunset.
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.
A rooftop terrace with a dining table, chairs, and a view of the cityscape, including the Water Tower Place building.
A woman sitting by a window with a city view, holding a cup and saucer.

7. Park Hyatt Chicago

Park Hyatt Chicago
Downtown Chicago
United States
Tom
£481
includes taxes & fees
1 Nov - 2 Nov
Park Hyatt 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 bar area with a central bar, multiple seating options, and a large chandelier.
A rooftop lounge with outdoor seating, a fire pit, and a large reflective sculpture.

8. The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago
Downtown Chicago
United States
Fred
£428
includes taxes & fees
1 Nov - 2 Nov
The Ritz-Carlton, Chicago
A restaurant with tables and chairs arranged in a corridor, large windows, and hanging lamps.
A rooftop pool area with city views, two lounge chairs, and a small table with a vase.
A dining area with wicker chairs and tables, overlooking a marina with boats and a Ferris wheel.
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
Xiomara
£522
includes taxes & fees
8 Nov - 9 Nov
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.
River Hotel

River Hotel

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£137
25 Oct - 26 Oct
includes taxes & fees
River Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

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£128
1 Nov - 2 Nov
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

172 W Adams St Chicago IL
£179
25 Oct - 26 Oct
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
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