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5 Stars Hotels in Southwest Side, Chicago from CA $295

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Check availability on Southwest Side 5 Star Hotels

Tonight
Sep 13 - Sep 14
Tomorrow
Sep 14 - Sep 15
Next weekend
Sep 18 - Sep 20
In two weeks
Sep 25 - Sep 27

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 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
Teresa
CA $915
CA $1,088 total
includes taxes & fees
Oct 4 - Oct 5
Four Seasons Hotel Chicago
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

Trump International Hotel & Tower Chicago
Downtown Chicago
United States
Jorge
CA $702
CA $835 total
includes taxes & fees
Sep 20 - Sep 21
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 spacious lobby with a modern sofa, armchairs, and a coffee table. A large window offers a view of the cityscape.

3. The Langham, Chicago

The Langham, Chicago
Downtown Chicago
United States
Saramae
CA $1,014
CA $1,206 total
includes taxes & fees
Oct 4 - Oct 5
The Langham, Chicago
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

The Peninsula Chicago
Downtown Chicago
United States
Angela
CA $1,040
CA $1,237 total
includes taxes & fees
Sep 20 - Sep 21
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
Jolanta Ewa
CA $884
CA $1,051 total
includes taxes & fees
Sep 20 - Sep 21
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 modern hotel room with a large window offering a city view, a wooden desk with a laptop, and a small seating area.
A modern lobby with a sofa, a coffee table, and a vase of flowers.
A modern hotel room with a large window, a wooden desk, a bathroom with a mirror, and a view of the cityscape.

6. Nobu Hotel Chicago

Nobu Hotel Chicago
Downtown Chicago
Canada
Jordan
CA $746
CA $922 total
includes taxes & fees
Oct 4 - Oct 5
Nobu Hotel 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 spacious lobby with a central seating area, a reception desk, and a large chandelier.

7. The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago
Downtown Chicago
Mexico
Andres
CA $895
CA $1,064 total
includes taxes & fees
Sep 20 - Sep 21
The Ritz-Carlton, 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 woman sitting by a window with a city view, holding a cup and saucer.
A rooftop terrace with a dining table, chairs, and a view of the cityscape, including the Water Tower Place building.

8. Park Hyatt Chicago

Park Hyatt Chicago
Downtown Chicago
United States
Catherine
CA $949
CA $1,128 total
includes taxes & fees
Sep 20 - Sep 21
Park Hyatt Chicago
A restaurant with tables and chairs arranged in a corridor, large windows, and hanging lamps.
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 rooftop pool area with city views, two lounge chairs, and a small table with a vase.

9. The St. Regis Chicago

The St. Regis Chicago
Downtown Chicago
United States
Xiomara
CA $931
CA $1,107 total
includes taxes & fees
Oct 4 - Oct 5
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.
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL
CA $248
CA $295 total
Oct 13 - Oct 14
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL
CA $383
CA $449 total
Sep 19 - Sep 20
includes taxes & fees
8.6/10 Excellent! (2,481 reviews)
Hilton Chicago O'Hare Airport
Hilton Chicago

Hilton Chicago

720 S Michigan Ave Chicago IL
CA $306
CA $405 total
Sep 25 - Sep 26
includes taxes & fees
Hilton Chicago
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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

Find out more about Southwest Side

Luxury is the name of the game at the best 5 Stars hotels in Southwest Side. If you want to vacation like a true VIP, these are the places to go; from spacious resorts to boutique-inspired hot spots, the top Southwest Side 5 Stars hotels are dedicated to immersing you in the ultimate experience. Want to relax with a serene treatment at a designer spa? These properties offer them.

Interested in tasting delicious dishes from top chefs? The gourmet restaurants at the 5 Stars Southwest Side hotels have you covered. You’ll even find first-class hotels near the city’s must-see attractions and most upscale entertainment districts. Plus, when you book your trip with Expedia.ca, you’ll get access to fantastic rates and seasonal discounts, so you can take advantage of a cheap deal on 5 Stars hotels Southwest Side without giving up even an inch of quality. Everything your heart desires (and a few perks designed to make it skip a beat): That’s what’s on offer when you plan a trip to the hotels with 5 Stars in Southwest Side.

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