Search for Cheap Deals on
5 Star Hotels in Woodlawn

Build your package with 2 more options
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!

Featured 5 Star Woodlawn Hotels

Four Seasons Hotel Chicago
5 out of 5
Fully refundableReserve now, pay when you stay
  • 21 min drive from Jackson Park
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
Get rates
Opens in a new windowFour Seasons Hotel Chicago
The Langham, Chicago
5 out of 5
Fully refundableReserve now, pay when you stay
  • 19 min drive from Jackson Park
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
Get rates
Opens in a new windowThe Langham, Chicago
The Peninsula Chicago
5 out of 5
Fully refundableReserve now, pay when you stay
  • 20 min drive from Jackson Park
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the property condition ...
Get rates
Opens in a new windowThe Peninsula Chicago
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Trump International Hotel & Tower Chicago
5 out of 5
Fully refundableReserve now, pay when you stay
  • 19 min drive from Jackson Park
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
Get rates
Opens in a new windowTrump International Hotel & Tower Chicago
Waldorf Astoria Chicago
5 out of 5
Fully refundableReserve now, pay when you stay
  • 21 min drive from Jackson Park
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
Get rates
Opens in a new windowWaldorf Astoria Chicago
Park Hyatt Chicago
5 out of 5
Fully refundableReserve now, pay when you stay
  • 20 min drive from Jackson Park
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
Get rates
Opens in a new windowPark Hyatt Chicago
Nobu Hotel Chicago
5 out of 5
Fully refundableReserve now, pay when you stay
  • 19 min drive from Jackson Park
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property ...
Get rates
Opens in a new windowNobu Hotel Chicago
The Ritz-Carlton, Chicago
5 out of 5
Fully refundableReserve now, pay when you stay
  • 20 min drive from Jackson Park
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. ...
Get rates
Opens in a new windowThe Ritz-Carlton, Chicago
The St. Regis Chicago
5 out of 5
Fully refundableReserve now, pay when you stay
  • 19 min drive from Jackson Park
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
Get rates
Opens in a new windowThe St. Regis Chicago
Art Villa
5 out of 5
  • 20 min drive from Jackson Park
Book a stay at this luxury aparthotel in Chicago. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions United Center and Chicago Riverwalk ...
Get rates
Opens in a new windowArt Villa
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.