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
$530 nightly
The price is $630 total per night from Aug 30 to Aug 31
$630 total
Aug 30 - Aug 31
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 ...
Trump International Hotel & Tower Chicago
401 N Wabash Ave Chicago IL
Fully refundableReserve now, pay when you stay
$469 nightly
The price is $557 total per night from Aug 16 to Aug 17
$557 total
Aug 16 - Aug 17
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 ...
The Langham, Chicago
330 North Wabash Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$531 nightly
The price is $631 total per night from Aug 30 to Aug 31
$631 total
Aug 30 - Aug 31
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! (1,004 reviews)
"This Hotel was amazing and within walking distance from everything. The farthest we had to walk was a mile but it didnt even fill like a mile with all the things to do and see. This is the only hotel that I have ever stayed in that cleans room twice a day. You will not be disappointed, very pricey ..."
Reviewed on Aug 6, 2026
The Peninsula Chicago
108 East Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
$625 nightly
The price is $743 total per night from Aug 23 to Aug 24
$743 total
Aug 23 - Aug 24
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)
"Best hotel in Chicago. Great location."
Reviewed on Aug 5, 2026
Waldorf Astoria Chicago
11 E. Walton Street Chicago IL
Fully refundableReserve now, pay when you stay
$536 nightly
The price is $637 total per night from Aug 23 to Aug 24
$637 total
Aug 23 - Aug 24
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 ...
The Ritz-Carlton, Chicago
160 E Pearson Street Chicago IL
Fully refundableReserve now, pay when you stay
$476 nightly
The price is $566 total per night from Aug 23 to Aug 24
$566 total
Aug 23 - Aug 24
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, ...
Nobu Hotel Chicago
155 N. Peoria Street Chicago IL
Fully refundableReserve now, pay when you stay
$436 nightly
The price is $518 total per night from Aug 30 to Aug 31
$518 total
Aug 30 - Aug 31
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 ...
Park Hyatt Chicago
800 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$554 nightly
The price is $658 total per night from Aug 23 to Aug 24
$658 total
Aug 23 - Aug 24
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, ...
The St. Regis Chicago
401 East Upper Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
$563 nightly
The price is $669 total per night from Aug 23 to Aug 24
$669 total
Aug 23 - Aug 24
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 ...
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
Hyatt Regency McCormick Place Chicago
4 out of 5
Posted 1 hour ago
Travelocity Verified Review
"It was fine"
A verified traveler stayed at Hyatt Regency McCormick Place Chicago
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