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Find 5 Star Hotels in Southwest Side, IL from ￥25,499

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Check availability on Southwest Side 5 Star Hotels

Tonight
Aug 29 - Aug 30
Tomorrow
Aug 30 - Aug 31
Next weekend
Sep 4 - Sep 6
In two weeks
Sep 11 - Sep 13

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.
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.
A couple walking through a spacious lobby with marble flooring, large white floral arrangements, and a modern staircase in the background.

1. Four Seasons Hotel Chicago

Four Seasons Hotel Chicago
Downtown Chicago
United States
August
￥89,650
￥106,585 total
includes taxes & fees
Sep 7 - Sep 8
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
￥81,046
￥96,355 total
includes taxes & fees
Sep 7 - Sep 8
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 modern dining area with round tables, comfortable chairs, and a dessert display.
A swimming pool with a ceiling of lights, large windows, and potted plants.

3. The Langham, Chicago

The Langham, Chicago
Downtown Chicago
United States
Michael
￥100,056
￥118,959 total
includes taxes & fees
Sep 7 - Sep 8
The Langham, Chicago
A high-rise hotel with multiple floors, large windows, and a prominent Tiffany & Co. store on the ground level.
A modern indoor pool area with large windows, potted palm plants, and lounge chairs.
A modern bar area with a checkered floor, bar stools, and a bartender.
A rooftop bar with seating and a view of the city skyline at night.

4. The Peninsula Chicago

The Peninsula Chicago
Downtown Chicago
United States
Angela
￥97,892
￥116,383 total
includes taxes & fees
Sep 7 - Sep 8
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 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
￥93,212
￥110,821 total
includes taxes & fees
Sep 7 - Sep 8
Waldorf Astoria Chicago
A modern indoor space with a glass ceiling, marble flooring, and contemporary furniture.
A modern lobby with a central seating area, large windows, and a decorative ceiling feature.
A rooftop lounge with outdoor seating, a fire pit, and a large reflective sculpture.
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
￥76,203
￥90,598 total
includes taxes & fees
Sep 27 - Sep 28
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 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.

7. Nobu Hotel Chicago

Nobu Hotel Chicago
Downtown Chicago
Canada
Jordan
￥69,263
￥86,348 total
includes taxes & fees
Aug 30 - Aug 31
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.

8. Park Hyatt Chicago

Park Hyatt Chicago
Downtown Chicago
United States
Jennifer
￥88,609
￥105,348 total
includes taxes & fees
Sep 7 - Sep 8
Park Hyatt Chicago
A restaurant with tables and chairs arranged in a corridor, large windows, and hanging lamps.
A dining area with wicker chairs and tables, overlooking a marina with boats and a Ferris wheel.
A rooftop pool area with city views, two lounge chairs, and a small table with a vase.
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
￥103,098
￥122,575 total
includes taxes & fees
Sep 21 - Sep 22
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
￥40,448
￥47,481 total
Sep 19 - Sep 20
includes taxes & fees
8.4/10 Very Good! (2,457 reviews)
Hilton Chicago O'Hare Airport
Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

2233 S Martin Luther King Dr Chicago IL
￥33,459
￥44,481 total
Aug 30 - Aug 31
includes taxes & fees
9.2/10 Wonderful! (1,333 reviews)
Hyatt Regency McCormick Place Chicago
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL
￥21,447
￥25,499 total
Aug 31 - Sep 1
includes taxes & fees
8/10 Very Good! (2,122 reviews)
The Chicago Hotel Collection Ambassador Gold Coast
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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

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