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Compare and book 5 Star hotels in Southwest Side, Chicago

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Check availability on Southwest Side 5 Star Hotels

Tonight
26 Oct - 27 Oct
Tomorrow
27 Oct - 28 Oct
This weekend
30 Oct - 1 Nov
Next weekend
6 Nov - 8 Nov

Our top choices for Southwest Side 5-star hotels

A person sitting by a window with a view of a cityscape, including a tall tower.
A group of people on a boat with a city skyline in the background.
An indoor swimming pool with a skylight, a lifeguard chair, and a potted plant.
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
ryan
£440
includes taxes & fees
22 Nov - 23 Nov
Four Seasons Hotel Chicago
A high-rise hotel with a prominent 'TRUMP' sign, reflecting in the water, surrounded by other tall buildings.
A modern hotel room with large windows, white furniture, and a view of tall buildings.
A cityscape with a river, a bridge, and a dining area with tables and chairs.
A modern hotel room with large floor-to-ceiling windows offering a city view.

2. Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago
Downtown Chicago
United States
Cecille
£410
includes taxes & fees
1 Nov - 2 Nov
Trump International Hotel & Tower 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.

3. The Peninsula Chicago

The Peninsula Chicago
Downtown Chicago
United States
Vincent Haley
£556
includes taxes & fees
15 Nov - 16 Nov
The Peninsula Chicago
A modern hotel lobby with a reception desk, seating area, and large windows offering city views.
A spacious lobby with a modern sofa, armchairs, and a coffee table. A large window offers a view of the cityscape.
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 modern dining area with round tables, comfortable chairs, and a dessert display.

4. The Langham, Chicago

The Langham, Chicago
Downtown Chicago
United States
Saramae
£464
includes taxes & fees
22 Nov - 23 Nov
The Langham, Chicago
A hotel entrance with a fountain, a car, and a person standing by the entrance.
A couple dining on a balcony with a cityscape view.
A bar area with a long counter, multiple stools, and a seating area with a booth.
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
£434
includes taxes & fees
22 Nov - 23 Nov
Waldorf Astoria Chicago
A rooftop lounge with outdoor seating, a fire pit, and a large reflective sculpture.
A modern lobby with a central seating area, large windows, and a decorative ceiling feature.
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.

6. The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago
Downtown Chicago
United States
Krikour
£343
includes taxes & fees
24 Nov - 25 Nov
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, a wooden desk, a bathroom with a mirror, and a view of the cityscape.
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
United States
Abhay
£301
includes taxes & fees
26 Nov - 27 Nov
Nobu Hotel Chicago
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 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.

8. Park Hyatt Chicago

Park Hyatt Chicago
Downtown Chicago
United States
Tom
£412
includes taxes & fees
22 Nov - 23 Nov
Park Hyatt Chicago
A modern hotel lobby with a large seating area, a view of the city, and a green accent wall.
A modern hotel entrance with a prominent "STREGIS" sign, large glass windows, and a well-lit facade.
A dining area with wicker chairs and tables, overlooking a marina with boats and a Ferris wheel.
A restaurant with tables and chairs arranged in a corridor, large windows, and hanging lamps.

9. The St. Regis Chicago

The St. Regis Chicago
Downtown Chicago
United States
Alise
£476
includes taxes & fees
22 Nov - 23 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 Southwest Side.
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL
£186
22 Nov - 23 Nov
includes taxes & fees
8.6/10 Excellent! (2,573 reviews)
Hilton Chicago O'Hare Airport
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

172 W Adams St Chicago IL
£106
22 Nov - 23 Nov
includes taxes & fees
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
River Hotel

River Hotel

75 East Wacker Drive Chicago IL
£103
22 Nov - 23 Nov
includes taxes & fees
8.8/10 Excellent! (5,569 reviews)
River Hotel
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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Explore attractions like Balzekas Museum of Lithuanian Culture and Ephraim Bajar Cultural Center as you discover things to see and do in Southwest Side.

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An airport with multiple runways, parked airplanes, and a large terminal building.
Photo by by Midway Intl Airport

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