Explore top 2025 5 Star Hotels in Woodlawn
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Top Woodlawn 5 Star hotels

Four Seasons Hotel Chicago
120 East Delaware Place, Chicago, IL
Fully refundableReserve now, pay when you stay
$445 nightly
The price is $522 total per night from Dec 7 to Dec 8
$522 total
Dec 7 - Dec 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 ...
9.4/10 Exceptional! (998 reviews)
staff very professional
Reviewed on Nov 9, 2025

The Langham, Chicago
330 North Wabash Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$457 nightly
The price is $536 total per night from Dec 11 to Dec 12
$536 total
Dec 11 - Dec 12
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, ...
9.6/10 Exceptional! (1,004 reviews)
Everything was great.
Reviewed on Nov 11, 2025

The Peninsula Chicago
108 East Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
$443 nightly
The price is $520 total per night from Dec 8 to Dec 9
$520 total
Dec 8 - Dec 9
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. ...
9.6/10 Exceptional! (1,002 reviews)
Historic hotel, located in a quiet neighborhood in the heart of the city, within walking distance of everything.
Reviewed on Nov 14, 2025

Trump International Hotel & Tower Chicago
401 N Wabash Ave Chicago IL
Fully refundableReserve now, pay when you stay
$394 nightly
The price is $462 total per night from Dec 7 to Dec 8
$462 total
Dec 7 - Dec 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 ...
9.4/10 Exceptional! (1,772 reviews)
It was absolutely wonderful. We were upgraded to a suite which was pretty sweet (no pun intended)! At night the surrounding view of the lake along the lakeside of the hotel was spectacular. The Rebar on the mezzanine floor with a live musician playing a saxophone on a Saturday, was a cozy and lively ...
Reviewed on Nov 14, 2025

Waldorf Astoria Chicago
11 E. Walton Street Chicago IL
Fully refundableReserve now, pay when you stay
$431 nightly
The price is $505 total per night from Dec 18 to Dec 19
$505 total
Dec 18 - Dec 19
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 ...
9.2/10 Wonderful! (1,000 reviews)
Beautiful place and service
Reviewed on Oct 29, 2025

Park Hyatt Chicago
800 N Michigan Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
$465 nightly
The price is $546 total per night from Dec 7 to Dec 8
$546 total
Dec 7 - Dec 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, ...
9.4/10 Exceptional! (999 reviews)
the stay was wonderful. Hospitality along with the room was great. thank you!
Reviewed on Nov 4, 2025

Nobu Hotel Chicago
155 N. Peoria Street Chicago IL
Fully refundableReserve now, pay when you stay
$314 nightly
The price is $369 total per night from Nov 25 to Nov 26
$369 total
Nov 25 - Nov 26
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 ...
9.2/10 Wonderful! (747 reviews)
Nice room, professional staff, nice welcome, perfect location
Reviewed on Nov 9, 2025

The Ritz-Carlton, Chicago
160 E Pearson Street, Chicago, IL
Fully refundableReserve now, pay when you stay
$402 nightly
The price is $472 total per night from Dec 17 to Dec 18
$472 total
Dec 17 - Dec 18
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, ...
9/10 Wonderful! (1,001 reviews)
Great breakfast a la carte menu, perfect bar setting, room was spotless, and service in accordance to the Ritz Brand.
Reviewed on Nov 14, 2025

The St. Regis Chicago
401 East Upper Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
$446 nightly
The price is $524 total per night from Dec 15 to Dec 16
$524 total
Dec 15 - Dec 16
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 ...
9/10 Wonderful! (79 reviews)
Room was wonderful
Reviewed on Nov 6, 2025

Art Villa
467 N Armour St Chicago IL
$534 nightly
The price is $660 total per night from Dec 18 to Dec 19
$660 total
Dec 18 - Dec 19
Total with taxes and fees
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
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.
Recent Woodlawn hotel reviews by fellow wanderers
citizenM Chicago Downtown
5 out of 5
Posted 1 day ago
Travelocity Verified Review
"El hotel está muy bien ubicado, es limpio y bonito. El staff es muy servicial y amable."
A verified traveler stayed at citizenM Chicago Downtown
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