Chicago Adventure Vacations
Book a Adventure Hotel + Flight or Car together to unlock savings
Better together
Save up to ￥45,448 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
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.
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
per person
Sep 15 - Sep 19
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,353 reviews)
Great property in great location. Would stay again. Rooms could be slightly more updated - stable doors for toilets not ideal for all. Carpets in need of a good deep clean.
Reviewed on Jul 4, 2025
Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
per person
Sep 15 - Sep 19
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,000 reviews)
Super unique hotel with gorgeous architecture. The bars and restaurants were fantastic and the view from Cindy's rooftop were amazing. The rooms are well-appointed and good sized. I'm very picky about my bed and it was comfy! Staff were so friendly and helpful. We loved the location and its walkable to Millenium Park, Lake Michigan, Riverwalk, Art Institute, train station and tons of restaurants and bars.
Reviewed on Jul 3, 2025
Silversmith Hotel Chicago Downtown
Downtown Chicago
per person
Sep 15 - Sep 19
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,840 reviews)
Absolutely loved the staff! The hotel was clean & quiet. I will definitely recommend it and I’ll be returning.
Reviewed on Jul 4, 2025
5* Adventure vacations in Chicago
Price found within the past 48 hours. Click for updated prices.
The Ritz-Carlton, Chicago
Downtown Chicago
per person
Sep 15 - Sep 19
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,002 reviews)
The lobby being on the 12th floor was a little different. Staff all very nice - not quite Four Seasons level but still pleasant and friendly. Really enjoyed the pool and dry sauna on the 11th floor, though regrettably the steam sauna was down for repair. One odd thing - the bathroom in our bedroom (I was there with my two kids), which has no lock, is one common area with the shower and toilet. So make a note - bathroom is one person at a time. No brushing your teeth while your kids use the can or shower (glass walled shower).
Reviewed on Jul 2, 2025
Four Seasons Hotel Chicago
Downtown Chicago
per person
Sep 15 - Sep 19
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
I believe the asst mgr name is Mason. He is was absolutely amazing. We will stay there again just because of him.
Reviewed on Jun 29, 2025
4 Night Adventure vacations in Chicago
Price found within the past 48 hours. Click for updated prices.
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
per person
Sep 15 - Sep 19
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,353 reviews)
Great property in great location. Would stay again. Rooms could be slightly more updated - stable doors for toilets not ideal for all. Carpets in need of a good deep clean.
Reviewed on Jul 4, 2025
Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
per person
Sep 15 - Sep 19
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,000 reviews)
Super unique hotel with gorgeous architecture. The bars and restaurants were fantastic and the view from Cindy's rooftop were amazing. The rooms are well-appointed and good sized. I'm very picky about my bed and it was comfy! Staff were so friendly and helpful. We loved the location and its walkable to Millenium Park, Lake Michigan, Riverwalk, Art Institute, train station and tons of restaurants and bars.
Reviewed on Jul 3, 2025
Top Adventure Chicago Hotels
Palmer House a Hilton Hotel
17 E Monroe St, Chicago, IL
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 Jun 30, 2025
Hyatt Regency McCormick Place Chicago
2233 S Martin Luther King Dr, Chicago, IL
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! (1,011 reviews)
"I did not find a menu of amenities in the area. I could not find a restaurant to eat in within walking distance. It was a very long walk from the hotel to the venue in McCormack Place. It might be nice to offer wheelchair rides. The swimming pool was closed for repairs."
Reviewed on Jul 2, 2025
Hyatt Regency Chicago
151 East Wacker Dr, Chicago, IL
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 Jul 3, 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.