Chicago Adventure Vacations
Book a Adventure Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥45,448 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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.
The Peninsula Chicago
Downtown Chicago
Price was ￥488,478, price is now ￥388,768 per person
￥388,768
per person
Jan 22 - Jan 27
found 11 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Service and clean room - paying attention to the details
Reviewed on Dec 22, 2025
Hilton Chicago
Downtown Chicago
Price was ￥252,018, price is now ￥200,755 per person
￥200,755
per person
Feb 22 - Feb 27
found 6 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
8.4/10 Very Good! (2,301 reviews)
Our stay at the Hilton Chicago was excellent. The staff was helpful and friendly, and we will consider staying at this hotel in the future.
Reviewed on Dec 22, 2025
The Ritz-Carlton, Chicago
Downtown Chicago
Price was ￥334,192, price is now ￥268,350 per person
￥268,350
per person
Jan 22 - Jan 27
found 6 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.2/10 Wonderful! (1,002 reviews)
The room was spotless and the bed super comfy. The staff was very helpful and extremely courteous.
Reviewed on Dec 15, 2025
Palmer House a Hilton Hotel
Downtown Chicago
Price was ￥241,425, price is now ￥197,374 per person
￥197,374
per person
Feb 22 - Feb 27
found 6 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
8.4/10 Very Good! (2,059 reviews)
Decent room and the staff at the front desk and restaurant were friendly and helpful. The front desk area is cramped and confusing (i.e.) once you get your key card from check-in, it is so tight in that area that that it’s unclear how you get out of the area without pushing past the people in line behind you.
Reviewed on Dec 22, 2025
5* Adventure vacations in Chicago
Price found within the past 48 hours. Click for updated prices.
The Ritz-Carlton, Chicago
Downtown Chicago
Price was ￥334,192, price is now ￥268,350 per person
￥268,350
per person
Jan 22 - Jan 27
found 6 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.2/10 Wonderful! (1,002 reviews)
The room was spotless and the bed super comfy. The staff was very helpful and extremely courteous.
Reviewed on Dec 15, 2025
The Peninsula Chicago
Downtown Chicago
Price was ￥478,845, price is now ￥375,622 per person
￥375,622
per person
Feb 22 - Feb 27
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Service and clean room - paying attention to the details
Reviewed on Dec 22, 2025
Four Seasons Hotel Chicago
Downtown Chicago
Price was ￥385,548, price is now ￥334,464 per person
￥334,464
per person
Feb 22 - Feb 27
found 6 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (999 reviews)
Such a wonderful stay at the Four Seasons Chicago. The newly designed hotel is beautiful. The room was beautiful, clean and inviting with crisp linens and plenty of pillows. I will be staying there again soon and already made my reservations.
Reviewed on Dec 21, 2025
Top Adventure Chicago Hotels
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
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! (2,168 reviews)
Decent room and the staff at the front desk and restaurant were friendly and helpful. The front desk area is cramped and confusing (i.e.) once you get your key card from check-in, it is so tight in that area that that it’s unclear how you get out of the area without pushing past the people in line ...
Reviewed on Dec 22, 2025
Hyatt Regency McCormick Place Chicago
2233 S Martin Luther King Dr Chicago IL
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! (1,038 reviews)
Beautiful room! Delicious breakfast!
Reviewed on Dec 20, 2025
Hyatt Regency Chicago
151 East Wacker Dr Chicago IL
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! (3,409 reviews)
Room was clean, staff was very pleasant and accommodating.
Reviewed on Dec 22, 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
