Explore top 2026 5 Star Hotels in Southwest Side

Name: The St. Regis Chicago
Price range: $798 total

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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

$557 total

Jul 12 - Jul 13

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! (1,918 reviews)

"Clean rooms staff were friendly and location was central. Beautiful bar and cities scenic view was perfect"

Reviewed on Jul 4, 2026

The Langham, Chicago

330 North Wabash Avenue Chicago IL

Fully refundableReserve now, pay when you stay

$500 nightly

$595 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 luxury hotel. Traveling on business? Take advantage of the 24-hour business center, ...

9.8/10 Exceptional! (1,002 reviews)

"Everything was mostly great. Except it was a bit overpriced (especially the spa) and minibar person kept adding stuff I didn't use to my bill. Also they don't tell you what perks you have depending on your reservation. You have to ask. Also I stayed in a junior suite for 8 days and they wouldn't ..."

Reviewed on Jul 2, 2026

Four Seasons Hotel Chicago

120 East Delaware Place Chicago IL

Fully refundableReserve now, pay when you stay

$530 nightly

$630 total

Jul 12 - Jul 13

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! (1,003 reviews)

"Excellent hotel. We love staying there whenever we visit Chicago."

Reviewed on Jul 3, 2026

The Peninsula Chicago

108 East Superior Street Chicago IL

Fully refundableReserve now, pay when you stay

$625 nightly

$743 total

Jul 12 - Jul 13

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! (1,001 reviews)

"This beautiful hotel never fails to live up to their reputation. Old school quality and service never disappoints."

Reviewed on Jul 3, 2026

Waldorf Astoria Chicago

11 E. Walton Street Chicago IL

Fully refundableReserve now, pay when you stay

$570 nightly

$678 total

Jul 19 - Jul 20

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! (1,000 reviews)

"Beautiful property with great location in Chicago. Can’t wait to stay again."

Reviewed on Jun 28, 2026

The Ritz-Carlton, Chicago

160 E Pearson Street Chicago IL

Fully refundableReserve now, pay when you stay

$575 nightly

$684 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, ...

9.2/10 Wonderful! (1,001 reviews)

"My wife and I had a reservation for the club level and up graded to a suite at ck in . It was NOT an upgrade . We shared a wall with the lounge kitchen . The smells constantly filled our room AND the cleaning crew started in the lounge at 1 AM making it hard to sleep until they finished cleaning ..."

Reviewed on Jun 30, 2026

Park Hyatt Chicago

800 N Michigan Ave Chicago IL

Fully refundableReserve now, pay when you stay

$587 nightly

$698 total

Jul 8 - Jul 9

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! (1,002 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

$437 nightly

$520 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! (882 reviews)

"The staff was friendly and helpful. They let us check in early, and I got an upgraded room. Very nice property, I would stay here again."

Reviewed on Jul 2, 2026

The St. Regis Chicago

401 East Upper Wacker Drive Chicago IL

Fully refundableReserve now, pay when you stay

$671 nightly

$798 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. Traveling on business? Take advantage of the free WiFi in public ...

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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.

Five Star Hotels in Southwest Side

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 five 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

The Chicago Hotel Collection - Magnificent Mile

4 out of 5

Posted 7 hours ago

Travelocity Verified Review

"The hotel and room were clean but there were a few areas of peeling wallpaper and paintwork that could be addressed. Staff at reception were very helpful but some at the breakfast buffet were not so. Better communication of what is/is not included in your rate would be an improvement. Great location as just 5 minutes from Michigan avenue."

A verified traveler stayed at The Chicago Hotel Collection - Magnificent Mile