
Chicago Adventure Vacations
Book a Adventure Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ₩234,741 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.

Club Quarters Hotel, Central Loop, Chicago
Downtown Chicago
Price was ₩1,813,676, price is now ₩1,555,456 per person
₩1,555,456
per person
May 13 - May 17
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
8.8/10 Excellent! (3,428 reviews)
Clean room, courteous staff and excellent facilities - meeting room and coffee machine...only demerit was the lack of a bureau in the room (vs a mini-bureau in the closet).
Reviewed on Mar 2, 2026

Hilton Chicago
Downtown Chicago
Price was ₩2,388,668, price is now ₩1,957,614 per person
₩1,957,614
per person
May 13 - May 17
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
8.6/10 Excellent! (2,658 reviews)
Perfect location, close to everywhere I wanted to go.
Reviewed on Mar 8, 2026


Palmer House a Hilton Hotel
Downtown Chicago
Price was ₩2,213,650, price is now ₩1,948,346 per person
₩1,948,346
per person
May 13 - May 17
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
8.6/10 Excellent! (2,311 reviews)
The property is friendly. Awesome location and lobby.
Reviewed on Mar 6, 2026

Swissotel - Chicago
Downtown Chicago
Price was ₩3,666,176, price is now ₩3,228,423 per person
₩3,228,423
per person
May 13 - May 17
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9/10 Wonderful! (3,198 reviews)
Great location and a perfect-sized hotel for a stay in Chicago! Our room had a beautiful view and was quiet, clean, and comfortable, with lovely linens and a huge bathroom. The workout room on the top floor is spacious and offers another stellar view of the city. We also appreciated the cozy lobby, which was just the right size and included a nice lobby bar and an adjacent restaurant.
One of our favorite features was the pedway system, which made it easy to get around while staying warm. If you’re looking for a less crowded, very comfortable hotel with great views and close proximity to Michigan Avenue, the river, and the lake, this is a great choice. My only downside was the cost of parking and how tight and confusing it was to navigate the parking garage “underworld.”
Reviewed on Mar 6, 2026
4 Night Adventure vacations in Chicago
Price found within the past 48 hours. Click for updated prices.


Hilton Chicago
Downtown Chicago
Price was ₩2,388,668, price is now ₩1,957,614 per person
₩1,957,614
per person
May 13 - May 17
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
8.6/10 Excellent! (2,658 reviews)
Perfect location, close to everywhere I wanted to go.
Reviewed on Mar 8, 2026

Hilton Garden Inn Chicago Downtown/Magnificent Mile
Downtown Chicago
Price was ₩2,177,078, price is now ₩1,785,922 per person
₩1,785,922
per person
May 13 - May 17
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
8.6/10 Excellent! (4,372 reviews)
Front desk is not looking welcoming. Rest location and property is good
Reviewed on Mar 8, 2026
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 ...
8.6/10 Excellent! (2,326 reviews)
All good
Reviewed on Mar 6, 2026

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 ...
9.2/10 Wonderful! (1,066 reviews)
Clean toom beautiful views
Reviewed on Mar 3, 2026

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 ...
9.4/10 Exceptional! (3,482 reviews)
More options for breakfast would be nice
Reviewed on Mar 6, 2026
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.
More Vacation Ideas
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
