Search for Cheap Deals on
5 Star Hotels in Woodlawn

Photo by Richard Remington

You choose what matters — star rating, location, amenities.

We pick the perfect hotel, packed with all your must-haves.

Your hotel is revealed right after booking, and you save up to 60%!

Featured 5 Star Woodlawn Hotels

Trump International Hotel & Tower Chicago
5 out of 5
Fully refundableReserve now, pay when you stay
  • 19 min drive from Jackson Park
The price is $462 per night from Nov 24 to Nov 25
$462
includes taxes & fees
Nov 24 - Nov 25
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
Trump International Hotel & Tower Chicago
The Peninsula Chicago
5 out of 5
Fully refundableReserve now, pay when you stay
  • 20 min drive from Jackson Park
The price is $616 per night from Nov 24 to Nov 25
$616
includes taxes & fees
Nov 24 - Nov 25
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the property condition ...
The Peninsula Chicago
The Langham, Chicago
5 out of 5
Fully refundableReserve now, pay when you stay
  • 19 min drive from Jackson Park
The price is $536 per night from Dec 8 to Dec 9
$536
includes taxes & fees
Dec 8 - Dec 9
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
The Langham, Chicago
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Waldorf Astoria Chicago
5 out of 5
Fully refundableReserve now, pay when you stay
  • 21 min drive from Jackson Park
The price is $436 per night from Dec 15 to Dec 16
$436
includes taxes & fees
Dec 15 - Dec 16
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
Waldorf Astoria Chicago
Nobu Hotel Chicago
5 out of 5
Fully refundableReserve now, pay when you stay
  • 19 min drive from Jackson Park
The price is $369 per night from Dec 15 to Dec 16
$369
includes taxes & fees
Dec 15 - Dec 16
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property ...
Nobu Hotel Chicago
Four Seasons Hotel Chicago
5 out of 5
Fully refundableReserve now, pay when you stay
  • 21 min drive from Jackson Park
The price is $517 per night from Dec 1 to Dec 2
$517
includes taxes & fees
Dec 1 - Dec 2
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the property ...
Four Seasons Hotel Chicago
Park Hyatt Chicago
5 out of 5
Fully refundableReserve now, pay when you stay
  • 20 min drive from Jackson Park
The price is $484 per night from Dec 8 to Dec 9
$484
includes taxes & fees
Dec 8 - Dec 9
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
Park Hyatt Chicago
The Ritz-Carlton, Chicago
5 out of 5
Fully refundableReserve now, pay when you stay
  • 20 min drive from Jackson Park
The price is $453 per night from Dec 15 to Dec 16
$453
includes taxes & fees
Dec 15 - Dec 16
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. ...
The Ritz-Carlton, Chicago
The St. Regis Chicago
5 out of 5
Fully refundableReserve now, pay when you stay
  • 19 min drive from Jackson Park
The price is $545 per night from Dec 15 to Dec 16
$545
includes taxes & fees
Dec 15 - Dec 16
Stay at this 5-star luxury hotel in Chicago. Enjoy a full-service spa, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
The St. Regis Chicago
Don't see what you're looking for?
See all available properties in Woodlawn
View all properties
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.