Chicago Adventure Vacations

Book a Adventure Hotel + Flight or Car together to unlock savings

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    Save up to ¥45,448 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Top Adventure vacation packages in Chicago

Price found within the past 48 hours. Click for updated prices.
Hotel Chicago Downtown, Autograph Collection by Marriott
Swissotel - Chicago
The Peninsula Chicago
Pendry Chicago
The Westin Chicago River North
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5* Adventure vacations in Chicago

Price found within the past 48 hours. Click for updated prices.
The Peninsula Chicago
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4 Night Adventure vacations in Chicago

Price found within the past 48 hours. Click for updated prices.
Hotel Chicago Downtown, Autograph Collection by Marriott
Swissotel - Chicago
Hyatt Place Chicago/River North
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See all available trips from Tokyo to Chicago
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Top Adventure Chicago Hotels

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
  • 12 min drive from Wrigley Field
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...
8.4/10 Very Good! (2,121 reviews)
W

Reviewed on Dec 2, 2025

Palmer House a Hilton Hotel
Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

4 out of 5
2233 S Martin Luther King Dr Chicago IL
  • 16 min drive from Wrigley Field
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
9/10 Wonderful! (1,035 reviews)
Would visit again

Reviewed on Nov 21, 2025

Hyatt Regency McCormick Place Chicago
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
151 East Wacker Dr Chicago IL
  • 11 min drive from Wrigley Field
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
9.2/10 Wonderful! (3,414 reviews)
I had a first time to visit Chicago with my family. We walked around the city, good experiences😊

Reviewed on Nov 29, 2025

Hyatt Regency Chicago
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.