Chicago Adventure Vacations

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

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    Better together
    Save up to NT$5,067 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy
    Plan, book, and manage your trip all in one place

Top Adventure vacation packages in Chicago

Price found within the past 48 hours. Click for updated prices.
Hilton Chicago
Swissotel - Chicago
The Royal Sonesta Chicago River North
The Royal Sonesta Chicago Downtown
Palmer House a Hilton Hotel
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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 spa hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff and ...
8.2/10 Very Good! (1,770 reviews)
Beautiful Hotel, didn’t like the small bathroom.
"Love the hotel!! It was beautiful but I didn’t like the bathroom in my room, it was very small and the sink didn’t have good drainage. Other than that, I enjoyed my stay ❤️❤️"

Reviewed on 2025/6/30

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
Stay at this 4-star eco-certified hotel in Chicago. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,008 reviews)
"Clean, modern rooms"

Reviewed on 2025/6/28

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
Stay at this 4-star eco-certified hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the bar and the helpful staff in our ...
9.2/10 Wonderful! (3,244 reviews)
"Very friendly, top spot, will stay here again!"

Reviewed on 2025/7/3

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.