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5 Stars Hotels in Southwest Side, Chicago from CA $294

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Check availability on Southwest Side 5 Star Hotels

Tonight
Sep 10 - Sep 11
Tomorrow
Sep 11 - Sep 12
This weekend
Sep 11 - Sep 13
Next weekend
Sep 18 - Sep 20

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

Four Seasons Hotel Chicago
Downtown Chicago
United States
Teresa
CA $911
CA $1,083 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 high-rise hotel with a prominent 'TRUMP' sign, reflecting in the water, surrounded by other tall buildings.
A modern hotel room with large floor-to-ceiling windows offering a city view.
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
Otilia
CA $699
CA $831 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 swimming pool with a ceiling of lights, large windows, and potted plants.
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

The Langham, Chicago
Downtown Chicago
United States
Michael
CA $955
CA $1,136 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 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.

4. The Peninsula Chicago

The Peninsula Chicago
Downtown Chicago
United States
Angela
CA $982
CA $1,167 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.
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.
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.

5. Waldorf Astoria Chicago

Waldorf Astoria Chicago
Downtown Chicago
United States
Jolanta Ewa
CA $836
CA $995 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 rooftop terrace with a view of a city skyline at dusk.
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.

6. Nobu Hotel Chicago

Nobu Hotel Chicago
Downtown Chicago
Canada
Jordan
CA $617
CA $768 total
includes taxes & fees
Sep 13 - Sep 14
Nobu Hotel Chicago
A modern indoor space with a glass ceiling, marble flooring, and contemporary furniture.
A modern bar area with a central bar, multiple seating options, and a large chandelier.
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.

7. The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago
Downtown Chicago
United States
Eric
CA $712
CA $847 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 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.

8. Park Hyatt Chicago

Park Hyatt Chicago
Downtown Chicago
United States
Catherine
CA $925
CA $1,100 total
includes taxes & fees
Oct 4 - Oct 5
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
United States
Xiomara
CA $926
CA $1,101 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 $247
CA $294 total
Sep 21 - Sep 22
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 $360
CA $422 total
Sep 11 - Sep 12
includes taxes & fees
8.4/10 Very good! (2,495 reviews)
Hilton Chicago O'Hare Airport
Hilton Chicago

Hilton Chicago

720 S Michigan Ave Chicago IL
CA $344
CA $449 total
Sep 11 - Sep 12
includes taxes & fees
8.6/10 Excellent! (3,168 reviews)
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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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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