Chicago Adventure Vacations
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Top Adventure vacation packages in Chicago
Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago Downtown
Downtown Chicago
Price was ￥84,366, price is now ￥68,344 per person
￥68,344
per person
Oct 24 - Oct 26
found 17 hours ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
9.2/10 Wonderful! (2,890 reviews)
Great stay with a wonderful view of the river. Clean and updated rooms.
Reviewed on Sep 9, 2025
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥100,722, price is now ￥82,896 per person
￥82,896
per person
Oct 24 - Oct 26
found 17 hours ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
9.4/10 Exceptional! (3,363 reviews)
The rooms, bars, and hotel property was great. However, I had a room on the 5th floor, NE corner, and it was truly impossible to sleep. I think I maybe slept about 10 hours in 3 days. The sirens and motorcycles were SO LOUD, All. Night. Long!!! Because of this, I would not stay here again.
Reviewed on Sep 9, 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 ￥516,997, price is now ￥353,401 per person
￥353,401
per person
Dec 1 - Dec 3
found 11 hours ago
Roundtrip flight included
Kagoshima (KOJ) to Chicago (ORD)
9.2/10 Wonderful! (1,001 reviews)
Too expensive for such a basic room. Cheap towels and toilet paper. Broken wall switches. Handle on bathroom door broke. Just a basic room with nothing special. No refrigerator or microwave. For almost $5000 for just 3 nights I had to pay for valet parking and all food (not even free snacks). Complimentary breakfast would have been great for $5000. Bathroom was nice but just a waste of money. Not sure what all the money was for. Will not recommend or ever go back.
Reviewed on Sep 1, 2025
Four Seasons Hotel Chicago
Downtown Chicago
Price was ￥539,754, price is now ￥371,083 per person
￥371,083
per person
Dec 1 - Dec 3
found 11 hours ago
Roundtrip flight included
Kagoshima (KOJ) to Chicago (ORD)
9.4/10 Exceptional! (1,003 reviews)
I loved it all. Brought my 5 year old grandson Mateo and they catered to him including their kid room key card , a treasure chest choice, a hat and stuffed animal and his own kid sized robe. He spilled some food in restaurant and we apologized profusely, but they waved it off saying they were family friendly. Loved the pool, loved the hot tub, loved how kind and friendly staff was
Reviewed on Aug 14, 2025
4 Night Adventure vacations in Chicago
Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North
Downtown Chicago
Price was ￥268,716, price is now ￥231,504 per person
￥231,504
per person
Nov 20 - Nov 24
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (2,078 reviews)
TV didn’t work correctly(Guide kept sticking). Need microwaves and better iron in rooms.
Reviewed on Sep 8, 2025
Pendry Chicago
Downtown Chicago
Price was ￥303,328, price is now ￥251,270 per person
￥251,270
per person
Nov 20 - Nov 24
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,070 reviews)
The property is gorgeous! Lovely rooms and the staff were fantastic, could not fault them at all! My only issue would be the roads outside are very noisy, we needed ear plugs to sleep. Other than that, absolutely fantastic stay! Would return and would highly recommend
Reviewed on Sep 8, 2025
Top Adventure Chicago Hotels
Palmer House a Hilton Hotel
17 E Monroe St, Chicago, IL
Stay at this 4-star luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...
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 ...
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 ...
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.
