Explore top 2025 5 Star Hotels in Southwest Side
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Top Southwest Side 5 Star hotels
Trump International Hotel & Tower Chicago
401 N Wabash Ave, Chicago, IL
$461 nightly
The price is $541 total per night from Oct 19 to Oct 20
$541 total
Oct 19 - Oct 20
Total with taxes and fees
A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly ...
9.4/10 Exceptional! (1,737 reviews)
"The hotel was above the expectations and river view was fabulous also staff were incredibly awesome specially the front dest employee Natalia she was helpful, smiling and welcoming."
Reviewed on Sep 24, 2025
The Langham, Chicago
330 North Wabash Avenue, Chicago, IL
$557 nightly
The price is $654 total per night from Oct 26 to Oct 27
$654 total
Oct 26 - Oct 27
Total with taxes and fees
A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, ...
9.6/10 Exceptional! (1,010 reviews)
"Y"
Reviewed on Sep 21, 2025
The Peninsula Chicago
108 East Superior Street, Chicago, IL
$675 nightly
The price is $792 total per night from Oct 5 to Oct 6
$792 total
Oct 5 - Oct 6
Total with taxes and fees
A full-service spa, 2 restaurants, and an indoor pool are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities and babysitting. ...
9.6/10 Exceptional! (1,013 reviews)
"Excellent hotel, my only complaint would be the Peninsula food service. We ate at the Shanghai Terrace our first night on site and honestly the food was only 2 stars. Specifically the appetizers were minuscule, and 90% pastry dough. Whatever filling was supposed to be inside all the dough largely ..."
Reviewed on Sep 27, 2025
Four Seasons Hotel Chicago
120 East Delaware Place, Chicago, IL
$590 nightly
The price is $693 total per night from Oct 26 to Oct 27
$693 total
Oct 26 - Oct 27
Total with taxes and fees
A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business ...
9.4/10 Exceptional! (1,005 reviews)
"Was very clean, although the toilet wasn’t flushing properly overall a great experience"
Reviewed on Sep 18, 2025
Waldorf Astoria Chicago
11 E. Walton Street, Chicago, IL
Fully refundableReserve now, pay when you stay
$602 nightly
The price is $706 total per night from Oct 13 to Oct 14
$706 total
Oct 13 - Oct 14
Total with taxes and fees
A full-service spa, a gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center, free WiFi ...
9.2/10 Wonderful! (1,006 reviews)
"Simply love this hotel"
Reviewed on Sep 18, 2025
Park Hyatt Chicago
800 N Michigan Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
$710 nightly
The price is $833 total per night from Oct 5 to Oct 6
$833 total
Oct 5 - Oct 6
Total with taxes and fees
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, ...
9.4/10 Exceptional! (1,001 reviews)
"Got pick pocketed in the elevator. I really like this hotel. Plan to return."
Reviewed on Sep 8, 2025
Nobu Hotel Chicago
155 N. Peoria Street, Chicago, IL
$525 nightly
The price is $616 total per night from Oct 30 to Oct 31
$616 total
Oct 30 - Oct 31
Total with taxes and fees
This luxury hotel includes 2 restaurants, an indoor pool, and a gym. Enjoy the steam room and perks like free WiFi. There's a bar/lounge on site, and a 24-hour ...
9.2/10 Wonderful! (729 reviews)
"Well appointed rooms with great service. The restaurant is decent too; there are also abundant dining options nearby that are open even on Labor Day."
Reviewed on Sep 25, 2025
The Ritz-Carlton, Chicago
160 E Pearson Street, Chicago, IL
Fully refundableReserve now, pay when you stay
$625 nightly
The price is $734 total per night from Oct 5 to Oct 6
$734 total
Oct 5 - Oct 6
Total with taxes and fees
A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center, ...
9/10 Wonderful! (1,006 reviews)
"Be prepared to be treated like you are the most important guest at the hotel. The staff here is incredibly professional, helpful and service oriented. Every single one."
Reviewed on Sep 15, 2025
The St. Regis Chicago
401 East Upper Wacker Drive, Chicago, IL
$625 nightly
The price is $734 total per night from Oct 5 to Oct 6
$734 total
Oct 5 - Oct 6
Total with taxes and fees
A full-service spa, 2 restaurants, and an indoor pool are all featured at this luxury hotel. Traveling on business? Take advantage of the free WiFi in public ...
9/10 Wonderful! (77 reviews)
"Clean room, amazing view"
Reviewed on Sep 7, 2025
Art Villa
467 N Armour St, Chicago, IL
A full-service spa and a hot tub are featured at this luxury aparthotel. Enjoy the a rooftop terrace and perks like free self parking and a free airport shuttle. ...
10/10 Exceptional! (2 reviews)
Reviewed on Aug 12, 2025
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.
Southwest Side Resorts & 5 Star Hotels
Looking for your own little slice of heaven during your next trip? Check out all the best 5-star hotels in Southwest Side to make sure your trip is as extravagantly comfortable as you expect.
Whether you plan on staying in your room the whole time or getting out and enjoying the city, you’ll be living the life while staying at your luxury accommodation. With so many amenities at your beck and call, you might try to turn your stay into a staycation!
Many of the 5-star hotels have award-winning restaurants you can dine at, as well as plush bedding and a concierge service to take care of your every need. Most also offer pools and modern fitness centers, not to mention high-speed Wi-Fi.
For your next trip, book a hotel that can be your own little hideaway, whether you’re in town for business or leisure. Southwest Side 5-star hotels provide you with all the comforts and amenities you expect from a sophisticated hotel, with a staff that’s happy to ensure you have everything you need to feel at home.
Whether you’re a first-time guest, or you’ve stayed in 5-star hotels in Southwest Side before, you’ll have no shortage of options to choose from on your next trip when you book with Travelocity. Browse our vast selection and find great deals on luxury lodging.
Recent Southwest Side hotel reviews by fellow wanderers
citizenM Chicago Downtown
5 out of 5
Posted 9 hours ago
Travelocity Verified Review
"This hotel is right off of Michigan Ave with many restaurants, stores, and museums. Excellent location."
A verified traveler stayed at citizenM Chicago Downtown
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