Explore top 2026 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
$400 nightly
The price is $470 total per night from Mar 1 to Mar 2
$470 total
Mar 1 - Mar 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 ...
9.2/10 Wonderful! (1,000 reviews)
Wonderful!
Reviewed on Feb 9, 2026
The Langham, Chicago
330 North Wabash Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$431 nightly
The price is $506 total per night from Mar 15 to Mar 16
$506 total
Mar 15 - Mar 16
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! (1,002 reviews)
Best service in Chicago — whether desk service, room service, etc. Stunning property. Amazing bathtubs.
Reviewed on Feb 12, 2026
The Peninsula Chicago
108 East Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
$525 nightly
The price is $616 total per night from Mar 1 to Mar 2
$616 total
Mar 1 - Mar 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. ...
9.6/10 Exceptional! (1,000 reviews)
Nice upgrade and amazing service
Reviewed on Feb 9, 2026
Trump International Hotel & Tower Chicago
401 N Wabash Ave Chicago IL
Fully refundableReserve now, pay when you stay
$371 nightly
The price is $436 total per night from Feb 23 to Feb 24
$436 total
Feb 23 - Feb 24
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! (1,844 reviews)
Fantastic!
Reviewed on Feb 12, 2026
Waldorf Astoria Chicago
11 E. Walton Street Chicago IL
Fully refundableReserve now, pay when you stay
$430 nightly
The price is $504 total per night from Mar 15 to Mar 16
$504 total
Mar 15 - Mar 16
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)
We loved our stay here! The staff was beyond attentive making our stay so special for our celebration! What an amazing hotel.
Reviewed on Feb 10, 2026
Park Hyatt Chicago
800 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$421 nightly
The price is $494 total per night from Feb 22 to Feb 23
$494 total
Feb 22 - Feb 23
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! (1,000 reviews)
Everything and everyone were excellent.
Reviewed on Feb 16, 2026
Nobu Hotel Chicago
155 N. Peoria Street Chicago IL
Fully refundableReserve now, pay when you stay
$291 nightly
The price is $342 total per night from Feb 27 to Feb 28
$342 total
Feb 27 - Feb 28
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! (789 reviews)
Customer service is great
Reviewed on Feb 17, 2026
The Ritz-Carlton, Chicago
160 E Pearson Street Chicago IL
Fully refundableReserve now, pay when you stay
$396 nightly
The price is $465 total per night from Mar 5 to Mar 6
$465 total
Mar 5 - Mar 6
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 room was spotless, the staff was incredibly courteous. I don't want to say anywhere else in Chicago
Reviewed on Feb 7, 2026
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 Mar 4 to Mar 5
$524 total
Mar 4 - Mar 5
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! (96 reviews)
The staff was exceptional, and the amenities, coupled with the stunning views of the river or city, make this a fantastic choice. The on-site restaurants provide convenient access to food. My only minor complaint is the absence of a mini fridge in the room to keep some drinks cool. I would definitely ...
Reviewed on Jan 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
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
Hilton Chicago
5 out of 5
Posted 1 day ago
Travelocity Verified Review
"The room was great and had a view over Grant Park. All the staff was courteous and helpful. The location is perfect if you want to site see. All within walking distance of the museums, the bean and navy pier. "
A verified traveler stayed at Hilton Chicago
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