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 River North
Downtown Chicago
per person
Sep 30 - Oct 4
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (1,866 reviews)
Great location right by the red line station and walkable to downtown and all the restaurants and sights. Family friendly and staff was very accommodating. Restaurant had great food too.
Reviewed on Jul 19, 2025
The Peninsula Chicago
Downtown Chicago
per person
Oct 9 - Oct 13
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.8/10 Exceptional! (1,002 reviews)
Everything about this hotel is on point. The staff is professional and gracious. The property is extremely well maintained. They leave no detail of your comfort unaddressed.
Reviewed on Jul 15, 2025
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
per person
Sep 30 - Oct 4
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (3,357 reviews)
The location of the hotel was perfect. A lot of restaurants and tourist attractions were walking distance and majority of the public transportation was near by as well
Reviewed on Jul 19, 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
Oct 13 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (1,001 reviews)
Dear Ritz-Carlton Team,
I wanted to take a moment to express my sincere gratitude for what was truly an unforgettable experience during my recent stay.
Having stayed in hundreds of hotels over the years, I can confidently say that nothing has ever come close to the level of service, hospitality, and excellence I encountered at your property. From the moment I arrived, every team member I interacted with was exceptionally respectful, attentive, and kind. The service was seamless and made me feel genuinely cared for at every turn.
The food was outstanding full of flavor and beautifully presented and it added to the overall sense of luxury and comfort that defined my stay.
I can say without hesitation that this is now the only hotel I’m willing to stay at when I travel. Thank you for having me. I look forward to returning and experiencing this exceptional level of care and luxury again.
Reviewed on Jul 6, 2025
The Peninsula Chicago
Downtown Chicago
per person
Oct 9 - Oct 13
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.8/10 Exceptional! (1,002 reviews)
Everything about this hotel is on point. The staff is professional and gracious. The property is extremely well maintained. They leave no detail of your comfort unaddressed.
Reviewed on Jul 15, 2025
3 Night Adventure vacations in Chicago
Price found within the past 48 hours. Click for updated prices.
Embassy Suites by Hilton Chicago Downtown River North
Downtown Chicago
per person
Oct 13 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.4/10 Very Good! (4,382 reviews)
Nice property in the midst of downtown. Easy to walk to different places (Starbucks, train station, corner store).
Reviewed on Jul 20, 2025
The Peninsula Chicago
Downtown Chicago
per person
Oct 13 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.8/10 Exceptional! (1,002 reviews)
Everything about this hotel is on point. The staff is professional and gracious. The property is extremely well maintained. They leave no detail of your comfort unaddressed.
Reviewed on Jul 15, 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
per person
Sep 30 - Oct 4
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (1,866 reviews)
Great location right by the red line station and walkable to downtown and all the restaurants and sights. Family friendly and staff was very accommodating. Restaurant had great food too.
Reviewed on Jul 19, 2025
The Peninsula Chicago
Downtown Chicago
per person
Oct 9 - Oct 13
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.8/10 Exceptional! (1,002 reviews)
Everything about this hotel is on point. The staff is professional and gracious. The property is extremely well maintained. They leave no detail of your comfort unaddressed.
Reviewed on Jul 15, 2025
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
per person
Sep 30 - Oct 4
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (3,357 reviews)
The location of the hotel was perfect. A lot of restaurants and tourist attractions were walking distance and majority of the public transportation was near by as well
Reviewed on Jul 19, 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! (1,784 reviews)
"Beautiful historic hotel! Loved the live music in the lobby. I was there in a traditional room sith 2 double beds, and then i upgraded to a suite. Both were nice rooms, but i LOVE a good suite! Personnel at the hotel were kind and helpful. Have a cocktail and a brownie in the lobby- you won't regret ..."
Reviewed on Jul 15, 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! (1,002 reviews)
"Great hotel! 2.5m from Rate Field!"
Reviewed on Jul 18, 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! (3,288 reviews)
"Valley service was great everyone was very kind"
Reviewed on Jul 17, 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.