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

$435 nightly

$511 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! (1,000 reviews)

I got the club suite and everything was beautiful and perfect. It was very clean and the walk in closet was awesome.

Reviewed on Apr 1, 2026

The Peninsula Chicago

108 East Superior Street Chicago IL

Fully refundableReserve now, pay when you stay

$525 nightly

$616 total

Apr 5 - Apr 6

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)

Awesome staff and over the top wonderful staff

Reviewed on Mar 30, 2026

Four Seasons Hotel Chicago

120 East Delaware Place Chicago IL

Fully refundableReserve now, pay when you stay

$400 nightly

$470 total

Apr 12 - Apr 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! (1,001 reviews)

Perfect!

Reviewed on Apr 3, 2026

Trump International Hotel & Tower Chicago

401 N Wabash Ave Chicago IL

Fully refundableReserve now, pay when you stay

$371 nightly

$436 total

Apr 12 - Apr 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 ...

9.4/10 Exceptional! (1,849 reviews)

Curtis who works front desk is 10/10 phenomenal everytime we are here he assists us and makes us feel so welcomed!

Reviewed on Apr 4, 2026

Park Hyatt Chicago

800 N Michigan Ave Chicago IL

Fully refundableReserve now, pay when you stay

$438 nightly

$514 total

Apr 7 - Apr 8

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! (1,001 reviews)

Amazing hotel. Excellent staff.

Reviewed on Mar 30, 2026

Waldorf Astoria Chicago

11 E. Walton Street Chicago IL

Fully refundableReserve now, pay when you stay

$471 nightly

$553 total

Apr 12 - Apr 13

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! (1,001 reviews)

It is really a beautiful hotel .. one of the best , I have ever stayed at

Reviewed on Mar 24, 2026

Nobu Hotel Chicago

155 N. Peoria Street Chicago IL

Fully refundableReserve now, pay when you stay

$339 nightly

$398 total

Apr 5 - Apr 6

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! (812 reviews)

We stayed for 2 nights. Our room was not cleaned. When asked housekeeping about cleaning our room we were told that as it was after 3 they will do a light clean up. The worst was that they did not replace our dirty coffee cups. This is very disappointing! Never expected this out of Nobu. I have never ...

Reviewed on Mar 30, 2026

The Ritz-Carlton, Chicago

160 E Pearson Street Chicago IL

Fully refundableReserve now, pay when you stay

$396 nightly

$465 total

Apr 12 - Apr 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 business center, ...

9.2/10 Wonderful! (1,000 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

$495 nightly

$581 total

Apr 5 - Apr 6

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! (104 reviews)

The hotel was extremely clean but the room itself reminded me of a nice condo, not a luxury hotel. Our room looked right into an apartment building with no view of the water. The restaurants, which were excellent, were highly overpriced, more so than at other nice restaurants in the city. We could ...

Reviewed on Mar 12, 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.

Recent Southwest Side hotel reviews by fellow wanderers

Hilton Chicago/Magnificent Mile Suites

5 out of 5

Posted 1 hour ago

Travelocity Verified Review

"Wonderful stay"

A verified traveler stayed at Hilton Chicago/Magnificent Mile Suites

Hilton Chicago

4 out of 5

Posted 14 hours ago

Travelocity Verified Review

"The hotel is very nice overall! We loved the games area in the lobby! Maybe it’s just that they’re extremely short staffed for the size of the place, but when disappointments keep happening you start to feel let down. Expect long lines at the front desk for check in or anything else. We couldn't get a response about getting an extra blanket for the room and they only have an automated system to help you with guest service. We also had to wait a couple hours for our luggage to get to the room after we arrived which was inconvenient. Also, heads up - we weren’t made aware at check in that the pool/hot tub area closes at 9:45 pm and that you need a reservation after 2:30 pm so we weren’t able to use either when we were there. That was a bummer for the kids since that’s why we booked this hotel!"

A verified traveler stayed at Hilton Chicago