Explore top 2026 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
Fully refundableReserve now, pay when you stay
$469 nightly
The price is $557 total per night from Aug 9 to Aug 10
$557 total
Aug 9 - Aug 10
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 ...
9.6/10 Exceptional! (1,934 reviews)
"We loved our "upgraded" room with the beautiful view of the river, Lake Michigan and the Saturday night fireworks! This was thanks to Michael, our concierge or check-in man at the front desk. It took us a little while to figure out all the lighting but that was a small thing. The coffee at your restaurant ..."
Reviewed on Jul 14, 2026
The Langham, Chicago
330 North Wabash Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$505 nightly
The price is $600 total per night from Aug 9 to Aug 10
$600 total
Aug 9 - Aug 10
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, ...
9.8/10 Exceptional! (1,014 reviews)
"The Langham was one of my favorite hotels I've ever stayed at. The shower was incredible, the bed felt like heaven and the overall room set-up was amazing. I especially loved the vanity! I also highly recommend the hotel restaurant for breakfast. I had breakfast there every day of my stay and it ..."
Reviewed on Jul 13, 2026
Four Seasons Hotel Chicago
120 East Delaware Place Chicago IL
Fully refundableReserve now, pay when you stay
$530 nightly
The price is $630 total per night from Aug 9 to Aug 10
$630 total
Aug 9 - Aug 10
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! (1,011 reviews)
"Liked the layout of our suite and that the hotel was right inside the shopping Mall & Bloomingdales."
Reviewed on Jul 13, 2026
The Peninsula Chicago
108 East Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
$625 nightly
The price is $743 total per night from Jul 19 to Jul 20
$743 total
Jul 19 - Jul 20
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. ...
9.8/10 Exceptional! (1,008 reviews)
"Who said you can’t work and play at the same time? Certainly not me. Chicago is a city that feels like home, no matter how much time passes. This trip has been all about balance... blending high-level work with the kind of downtime only The Peninsula can provide. It’s been a perfect backdrop for ..."
Reviewed on Jul 13, 2026
Waldorf Astoria Chicago
11 E. Walton Street Chicago IL
Fully refundableReserve now, pay when you stay
$513 nightly
The price is $609 total per night from Aug 9 to Aug 10
$609 total
Aug 9 - Aug 10
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 ...
9.4/10 Exceptional! (1,003 reviews)
"Very nice room with terrace. Great Staff"
Reviewed on Jul 5, 2026
The Ritz-Carlton, Chicago
160 E Pearson Street Chicago IL
Fully refundableReserve now, pay when you stay
$546 nightly
The price is $649 total per night from Jul 26 to Jul 27
$649 total
Jul 26 - Jul 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 business center, ...
Park Hyatt Chicago
800 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$554 nightly
The price is $658 total per night from Aug 9 to Aug 10
$658 total
Aug 9 - Aug 10
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, ...
9.6/10 Exceptional! (1,006 reviews)
"Arrived 4:30PM, room not ready. Left bags with Bell Desk and went to a business dinner. Returned at 8pm, Bell Desk could not find my bags. Arrived an hour later, they had put them in the wrong room. No offer of any kind to remedy or try to remedy, just “sorry”. Shameful."
Reviewed on Jul 3, 2026
Nobu Hotel Chicago
155 N. Peoria Street Chicago IL
Fully refundableReserve now, pay when you stay
$475 nightly
The price is $565 total per night from Jul 26 to Jul 27
$565 total
Jul 26 - Jul 27
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 ...
9.4/10 Exceptional! (885 reviews)
"Stunning hotel with really attentive staff, located in the heart of Chicago's West Loop neighborhood. You are surrounded by a ton of award-winning restaurants, shopping and also close to public transit. Rooms are spacious and are themed in a minimalistic Japanese onsen-style esthetic. We loved our ..."
Reviewed on Jul 6, 2026
The St. Regis Chicago
401 East Upper Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
$707 nightly
The price is $841 total per night from Aug 9 to Aug 10
$841 total
Aug 9 - Aug 10
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 ...
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
Hotel Riu Plaza Chicago
5 out of 5
Posted 2 hours ago
Travelocity Verified Review
"The breakfast buffet was amazing. Did not expect that size and quality of selections and also well-organized and well-staffed. The rooftop lounge was beautiful and inviting. You can go there even if you don’t order anything but we enjoyed a dessert and drinks. The view was so cool with the see-through ledge you can walk onto. Perfect location to enjoy Magnificent Mile just down the street and so many other places to enjoy within walking distance. 100% recommend and will return!"
A verified traveler stayed at Hotel Riu Plaza Chicago
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