The Best 5 Star Hotels in Southwest Side, IL from AED 527 | Expedia

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Check availability on Southwest Side 5 Star Hotels

Tonight

19 Oct - 20 Oct

Tomorrow

20 Oct - 21 Oct

This weekend

23 Oct - 25 Oct

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

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

Downtown Chicago

United States

Edda

AED 1,928

AED 2,293 total

includes taxes & fees

15 Nov - 16 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 modern hotel room with large windows, white furniture, and a view of tall buildings.

A modern hotel room with large floor-to-ceiling windows offering a city view.

2. Trump International Hotel & Tower Chicago

Downtown Chicago

United States

Cecille

AED 1,694

AED 2,014 total

includes taxes & fees

1 Nov - 2 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 modern dining area with round tables, comfortable chairs, and a dessert display.

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.

3. The Langham, Chicago

Downtown Chicago

United States

Saramae

AED 1,917

AED 2,280 total

includes taxes & fees

15 Nov - 16 Nov

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

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.

A rooftop bar with seating and a view of the city skyline at night.

4. The Peninsula Chicago

Downtown Chicago

United States

Melinda

AED 2,296

AED 2,729 total

includes taxes & fees

1 Nov - 2 Nov

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

A couple dining on a balcony with a cityscape view.

5. Waldorf Astoria Chicago

Downtown Chicago

United States

Luis

AED 1,936

AED 2,301 total

includes taxes & fees

15 Nov - 16 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.

6. Nobu Hotel Chicago

Downtown Chicago

United States

Abhay

AED 1,670

AED 2,078 total

includes taxes & fees

15 Nov - 16 Nov

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.

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.

7. Park Hyatt Chicago

Downtown Chicago

United States

Tom

AED 2,000

AED 2,378 total

includes taxes & fees

15 Nov - 16 Nov

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 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.

8. The Ritz-Carlton, Chicago

Downtown Chicago

United States

Krikour

AED 1,858

AED 2,209 total

includes taxes & fees

1 Nov - 2 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.

River Hotel

River Hotel

75 East Wacker Drive Chicago IL

AED 559

AED 664 total

1 Nov - 2 Nov

includes taxes & fees

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

AED 443

AED 527 total

11 Nov - 12 Nov

includes taxes & fees

8/10 Very Good! (2,530 reviews)

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

172 W Adams St Chicago IL

AED 621

AED 738 total

1 Nov - 2 Nov

includes taxes & fees

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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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