Explore top 2026 5 Star Hotels in Southwest Side

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Top Southwest Side 5 Star hotels

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
120 East Delaware Place Chicago IL
$525 nightly
The price is $624 total per night from Nov 1 to Nov 2
$624 total
Nov 1 - Nov 2
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! (1,004 reviews)
"Was amazing experience we want to go back"

Reviewed on Oct 5, 2026

Opens in a new windowFour Seasons Hotel Chicago
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
401 N Wabash Ave Chicago IL
$461 nightly
The price is $548 total per night from Nov 1 to Nov 2
$548 total
Nov 1 - Nov 2
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! (2,045 reviews)
"Hands down the best hotel in Chicago!"

Reviewed on Oct 5, 2026

Opens in a new windowTrump International Hotel & Tower Chicago
The Langham, Chicago

The Langham, Chicago

5 out of 5
330 North Wabash Avenue Chicago IL
$536 nightly
The price is $637 total per night from Nov 1 to Nov 2
$637 total
Nov 1 - Nov 2
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)
"Our room was exceptionally clean with all the amenities. And we were especially impressed by the staff - everyone was friendly and anxious to help. A most enjoyable stay. We look forward to the next! 46676"

Reviewed on Oct 3, 2026

Opens in a new windowThe Langham, Chicago
The Peninsula Chicago

The Peninsula Chicago

5 out of 5
108 East Superior Street Chicago IL
$625 nightly
The price is $743 total per night from Nov 1 to Nov 2
$743 total
Nov 1 - Nov 2
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. ...
Opens in a new windowThe Peninsula Chicago
Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
11 E. Walton Street Chicago IL
$553 nightly
The price is $658 total per night from Nov 1 to Nov 2
$658 total
Nov 1 - Nov 2
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)
"Treated myself to a little local getaway for my birthday, and it was exactly what I needed. Demi was the best, Alyssa gave the most amazing massages, the food was delicious, and everything was so comfortable. Such a perfect birthday treat! 💕✨"

Reviewed on Oct 5, 2026

Opens in a new windowWaldorf Astoria Chicago
Nobu Hotel Chicago

Nobu Hotel Chicago

5 out of 5
155 N. Peoria Street Chicago IL
$476 nightly
The price is $566 total per night from Nov 1 to Nov 2
$566 total
Nov 1 - Nov 2
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 ...
Opens in a new windowNobu Hotel Chicago
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
800 N Michigan Ave Chicago IL
$543 nightly
The price is $645 total per night from Nov 1 to Nov 2
$645 total
Nov 1 - Nov 2
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, ...
Opens in a new windowPark Hyatt Chicago
The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago

5 out of 5
160 E Pearson Street Chicago IL
$476 nightly
The price is $566 total per night from Nov 1 to Nov 2
$566 total
Nov 1 - Nov 2
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)
"The hotel was beautiful, the room was comfortable, and the staff was welcoming and attentive. Everything was clean and well maintained, and the location made it easy to get around the city. Overall, it was a really nice stay and I’d definitely consider coming back."

Reviewed on Sep 24, 2026

Opens in a new windowThe Ritz-Carlton, Chicago
The St. Regis Chicago

The St. Regis Chicago

5 out of 5
401 East Upper Wacker Drive Chicago IL
$626 nightly
The price is $744 total per night from Oct 29 to Oct 30
$744 total
Oct 29 - Oct 30
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 ...
Opens in a new windowThe St. Regis Chicago
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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

River Hotel

River Hotel

5 out of 5
Posted 5 hours ago
Travelocity Verified Review
"Wonderful experience. So close to the river walk and activities. Staff was so helpful and attentive and property was clean and comfy! Highly recommend!"
A verified traveler stayed at River Hotel
River Hotel

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