Explore top 2026 5 Star Hotels in Southwest Side

Name: Art Villa
Rating: 10

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Top Southwest Side 5 Star hotels

The Langham, Chicago

330 North Wabash Avenue Chicago IL

Fully refundableReserve now, pay when you stay

$450 nightly

$528 total

Apr 26 - Apr 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! (1,006 reviews)

The Langham far exceeded my expectations I had. The level of service start to finish was truly 5 stars. I cannot recommend staying there enough.

Reviewed on Apr 7, 2026

The Peninsula Chicago

108 East Superior Street Chicago IL

Fully refundableReserve now, pay when you stay

$525 nightly

$616 total

Apr 12 - Apr 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! (1,004 reviews)

A beautiful hotel with high end amenities. Stayed for a vacation weekend and it was everything we needed!

Reviewed on Apr 6, 2026

Four Seasons Hotel Chicago

120 East Delaware Place Chicago IL

Fully refundableReserve now, pay when you stay

$410 nightly

$481 total

Apr 26 - Apr 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! (1,000 reviews)

Beautiful and in walking distance to so many shops and cafes! We had a great stay.

Reviewed on Apr 6, 2026

Trump International Hotel & Tower Chicago

401 N Wabash Ave Chicago IL

Fully refundableReserve now, pay when you stay

$371 nightly

$436 total

Apr 19 - Apr 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! (1,848 reviews)

Beautiful facility, excellent service, professional staff, delicious food!

Reviewed on Apr 7, 2026

Park Hyatt Chicago

800 N Michigan Ave Chicago IL

Fully refundableReserve now, pay when you stay

$438 nightly

$514 total

Apr 12 - Apr 13

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! (1,000 reviews)

Service is amazing. They will do anything to make your stay better.

Reviewed on Apr 5, 2026

Waldorf Astoria Chicago

11 E. Walton Street Chicago IL

Fully refundableReserve now, pay when you stay

$453 nightly

$532 total

Apr 19 - Apr 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)

Top of the line customer service! I can’t express how deeply I am impressed with your hotel, the feel, the specialness of it all! My first time there, has left me with a lasting impression I will never forget! Classy and it smelled like Paris! Love everything about the hotel. Wish I could have stayed ...

Reviewed on Apr 6, 2026

Nobu Hotel Chicago

155 N. Peoria Street Chicago IL

Fully refundableReserve now, pay when you stay

$339 nightly

$398 total

Apr 19 - Apr 20

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! (814 reviews)

Comfy bed, lovely room, welcoming staff, good amenities

Reviewed on Apr 8, 2026

The Ritz-Carlton, Chicago

160 E Pearson Street Chicago IL

Fully refundableReserve now, pay when you stay

$396 nightly

$465 total

Apr 19 - Apr 20

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)

Enjoyed a very comfortable stay.

Reviewed on Mar 30, 2026

The St. Regis Chicago

401 East Upper Wacker Drive Chicago IL

Fully refundableReserve now, pay when you stay

$536 nightly

$629 total

Apr 24 - Apr 25

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 ...

9.2/10 Wonderful! (105 reviews)

Great hotel, large pool - although I wish it was a bit warmer for my liking. The hot sauna though was a nice addition ( there is no hut tub in the pool area). Large gym was also great- unbelievable views of Lake Michigan and Navy Pier!

Reviewed on Apr 6, 2026

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

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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.