5 Stars Hotels in Southwest Side: Special Rates & Discounts | Expedia

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Check availability on Southwest Side 5 Star Hotels

Tonight

26 Oct - 27 Oct

Tomorrow

27 Oct - 28 Oct

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Next weekend

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 group of people on a boat with a city skyline in the background.

1. Four Seasons Hotel Chicago

Downtown Chicago

United States

ryan

HK$3,882

HK$4,615 total

includes taxes & fees

22 Nov - 23 Nov

A cityscape with a river, a bridge, and a dining area with tables and chairs.

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.

A modern hotel room with large windows, white furniture, and a view of tall buildings.

2. Trump International Hotel & Tower Chicago

Downtown Chicago

United States

Cecille

HK$3,617

HK$4,301 total

includes taxes & fees

1 Nov - 2 Nov

A high-rise hotel with multiple floors, large windows, and a prominent Tiffany & Co. store on the ground level.

A modern bar area with a checkered floor, bar stools, and a bartender.

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.

3. The Peninsula Chicago

Downtown Chicago

United States

Vincent Haley

HK$4,902

HK$5,827 total

includes taxes & fees

15 Nov - 16 Nov

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 swimming pool with a ceiling of lights, large windows, and potted plants.

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.

4. The Langham, Chicago

Downtown Chicago

United States

Saramae

HK$4,094

HK$4,867 total

includes taxes & fees

22 Nov - 23 Nov

A black luxury car parked in front of a hotel entrance with a glass canopy decorated with festive ornaments.

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.

A bar area with a polished marble floor, bar stools, a counter with bottles, and a decorative lamp.

5. Waldorf Astoria Chicago

Downtown Chicago

United States

Luis

HK$3,833

HK$4,557 total

includes taxes & fees

22 Nov - 23 Nov

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

Downtown Chicago

United States

Krikour

HK$3,029

HK$3,601 total

includes taxes & fees

24 Nov - 25 Nov

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 modern lobby with a sofa, a coffee table, and a vase of flowers.

A rooftop terrace with a view of a city skyline at dusk.

7. Nobu Hotel Chicago

Downtown Chicago

United States

Abhay

HK$2,489

HK$3,155 total

includes taxes & fees

26 Nov - 27 Nov

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

Downtown Chicago

United States

Tom

HK$3,635

HK$4,322 total

includes taxes & fees

22 Nov - 23 Nov

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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

HK$1,660

HK$1,949 total

22 Nov - 23 Nov

includes taxes & fees

8.6/10 Excellent! (2,577 reviews)

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

172 W Adams St Chicago IL

HK$933

HK$1,110 total

22 Nov - 23 Nov

includes taxes & fees

River Hotel

River Hotel

75 East Wacker Drive Chicago IL

HK$910

HK$1,082 total

22 Nov - 23 Nov

includes taxes & fees

8.8/10 Excellent! (5,573 reviews)

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Pool Spa Hot tub Breakfast included Waterpark

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.

See all hotels in Southwest Side

An airport with multiple runways, parked airplanes, and a large terminal building.

Top Southwest Side Hotel Reviews

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