Explore top 2026 5 Star Hotels in Southwest Side
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Top Southwest Side 5 Star hotels
Four Seasons Hotel Chicago
120 East Delaware Place Chicago IL
Fully refundableReserve now, pay when you stay
$420 nightly
The price is $493 total per night from Jan 11 to Jan 12
$493 total
Jan 11 - Jan 12
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 ...
9.2/10 Wonderful! (998 reviews)
Staff, amenities, special touches for kids
Reviewed on Dec 29, 2025
The Langham, Chicago
330 North Wabash Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$413 nightly
The price is $485 total per night from Feb 1 to Feb 2
$485 total
Feb 1 - Feb 2
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! (1,003 reviews)
Best hotel in Chicago. We’ve been to around 25.
Reviewed on Dec 28, 2025
The Peninsula Chicago
108 East Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
$475 nightly
The price is $558 total per night from Jan 4 to Jan 5
$558 total
Jan 4 - Jan 5
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! (1,017 reviews)
Emil was a fabulous server at the Lobby Restaurant. I think that’s his name. Tall guy. Becca at front desk also fantastic. The lady who checked us in not so good.
Reviewed on Dec 29, 2025
Trump International Hotel & Tower Chicago
401 N Wabash Ave Chicago IL
Fully refundableReserve now, pay when you stay
$319 nightly
The price is $374 total per night from Jan 11 to Jan 12
$374 total
Jan 11 - Jan 12
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! (1,810 reviews)
Check in was smooth. Each Trump team member was welcoming, knowledgeable and efficient. My room was upgraded on a complementary basis. The room was well equipped, large, had a great view of the city and was clean and comfortable. The fitness center was was exceptionally equipped and spacious.The ...
Reviewed on Dec 28, 2025
Waldorf Astoria Chicago
11 E. Walton Street Chicago IL
Fully refundableReserve now, pay when you stay
$380 nightly
The price is $446 total per night from Feb 1 to Feb 2
$446 total
Feb 1 - Feb 2
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! (1,003 reviews)
Super comfortable bed, and the deep bathtub alone is worth the stay!
Reviewed on Dec 26, 2025
Park Hyatt Chicago
800 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$387 nightly
The price is $454 total per night from Jan 5 to Jan 6
$454 total
Jan 5 - Jan 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! (999 reviews)
Great
Reviewed on Dec 17, 2025
Nobu Hotel Chicago
155 N. Peoria Street Chicago IL
Fully refundableReserve now, pay when you stay
$319 nightly
The price is $374 total per night from Jan 4 to Jan 5
$374 total
Jan 4 - Jan 5
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! (769 reviews)
Staff were excellent, room was large and spotless. Would definitely return to Nobu Chicago
Reviewed on Dec 29, 2025
The Ritz-Carlton, Chicago
160 E Pearson Street Chicago IL
Fully refundableReserve now, pay when you stay
$386 nightly
The price is $453 total per night from Feb 1 to Feb 2
$453 total
Feb 1 - Feb 2
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! (1,002 reviews)
I have nothing but great things to say about my stay. I’ve stayed at another five-star hotel in the same area, and the level of service here far surpassed my previous experience. I would absolutely recommend this hotel.
Reviewed on Dec 27, 2025
The St. Regis Chicago
401 East Upper Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
$446 nightly
The price is $524 total per night from Feb 1 to Feb 2
$524 total
Feb 1 - Feb 2
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! (86 reviews)
All the anove
Reviewed on Dec 15, 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
Hilton Chicago
5 out of 5
Posted 4 hours ago
Travelocity Verified Review
"Yes it was a great stay"
A verified traveler from Greensboro stayed at Hilton Chicago
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