Explore top 2026 5 Star Hotels in Southwest Side

Name: The St. Regis Chicago
Price range: $766 total
Rating: 9.4

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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

$555 nightly

$660 total

Sep 7 - Sep 8

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 ...

Trump International Hotel & Tower Chicago

401 N Wabash Ave Chicago IL

Fully refundableReserve now, pay when you stay

$506 nightly

$602 total

Sep 7 - Sep 8

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! (1,988 reviews)

"隔音效果差"

Reviewed on Aug 27, 2026

The Langham, Chicago

330 North Wabash Avenue Chicago IL

Fully refundableReserve now, pay when you stay

$620 nightly

$737 total

Aug 30 - Aug 31

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, ...

The Peninsula Chicago

108 East Superior Street Chicago IL

Fully refundableReserve now, pay when you stay

$625 nightly

$743 total

Aug 30 - Aug 31

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! (1,000 reviews)

"The service and the staff iare incredible, do professional!! So many details! My husband and I were so happy!!"

Reviewed on Aug 25, 2026

Waldorf Astoria Chicago

11 E. Walton Street Chicago IL

Fully refundableReserve now, pay when you stay

$582 nightly

$692 total

Sep 7 - Sep 8

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 ...

The Ritz-Carlton, Chicago

160 E Pearson Street Chicago IL

Fully refundableReserve now, pay when you stay

$476 nightly

$566 total

Sep 27 - Sep 28

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, ...

Nobu Hotel Chicago

155 N. Peoria Street Chicago IL

Fully refundableReserve now, pay when you stay

$454 nightly

$539 total

Aug 30 - Aug 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 ...

9.4/10 Exceptional! (919 reviews)

"Loved everything! Check in was super fast! Arrived by 10:30am and room wasn’t available. I had reservations for 12pm, the receptionist gave my daughter and I the option to use the wellness center to freshen up and change, and I absolutely loved it. The amenities were all great! Our room was ready ..."

Reviewed on Aug 27, 2026

Park Hyatt Chicago

800 N Michigan Ave Chicago IL

Fully refundableReserve now, pay when you stay

$565 nightly

$672 total

Aug 31 - Sep 1

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, ...

The St. Regis Chicago

401 East Upper Wacker Drive Chicago IL

Fully refundableReserve now, pay when you stay

$644 nightly

$766 total

Sep 21 - Sep 22

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 ...

9.4/10 Exceptional! (129 reviews)

"One night at The St. Regis Chicago ✨ Beautiful views, incredible service, and the perfect little luxury escape in the heart of the city. Short stay, but absolutely worth it. 🤍"

Reviewed on Aug 15, 2026

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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.