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5 Star Hotels in Southwest Side, Chicago

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Check availability on Southwest Side 5 Star Hotels

Tonight
4 Oct - 5 Oct
Tomorrow
5 Oct - 6 Oct
Next weekend
9 Oct - 11 Oct
In two weeks
16 Oct - 18 Oct

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 modern bar area with a central bar and multiple stools, surrounded by a high ceiling with a decorative light fixture.
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.

1. Four Seasons Hotel Chicago

Four Seasons Hotel Chicago
Downtown Chicago
United States
Teresa
€570
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 floor-to-ceiling windows offering a city view.
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.

2. Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago
Downtown Chicago
United States
Mark
€487
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 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.
A modern dining area with round tables, comfortable chairs, and a dessert display.

3. The Langham, Chicago

The Langham, Chicago
Downtown Chicago
United States
Saramae
€575
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
€660
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.
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.
A bar area with a long counter, multiple stools, and a seating area with a booth.
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
Luis
€570
includes taxes & fees
1 Nov - 2 Nov
Waldorf Astoria Chicago
A modern indoor swimming pool with a clear blue water surface, a wooden ceiling, and a wall with a floral pattern.
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.
A modern hotel room with a large window offering a city view, a wooden desk with a laptop, and a small seating area.

6. Nobu Hotel Chicago

Nobu Hotel Chicago
Downtown Chicago
United States
Abhay
€503
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 hotel room with a large bed, a seating area, a TV, and a view of the city and ocean.
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
€593
includes taxes & fees
1 Nov - 2 Nov
Park Hyatt Chicago
A modern indoor space with a glass ceiling, marble flooring, and contemporary furniture.
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 bar area with a central bar, multiple seating options, and a large chandelier.

8. The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago
Downtown Chicago
United States
Fred
€503
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 entrance with a prominent "STREGIS" sign, large glass windows, and a well-lit facade.

9. The St. Regis Chicago

The St. Regis Chicago
Downtown Chicago
United States
Xiomara
€661
includes taxes & fees
29 Oct - 30 Oct
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.
River Hotel

River Hotel

75 East Wacker Drive Chicago IL
€176
1 Nov - 2 Nov
includes taxes & fees
River Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL
€151
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
€193
25 Oct - 26 Oct
includes taxes & fees
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio 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.

Learn more about Southwest Side

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

Top Southwest Side Hotel Reviews

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