Chicago Adventure Holidays
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Top flight + Adventure hotel deals in Chicago
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Downtown Chicago
per person
4 Sept - 7 Sept
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
8.8/10 Excellent! (2,274 reviews)
There was an issue with my room and the manager quickly rectified the situation. Swissotel is top notch for customer service!
Reviewed on 5 Jul 2025
5* Adventure holidays in Chicago
Price found within the past 48 hours. Click for updated prices.
Four Seasons Hotel Chicago
Downtown Chicago
per person
4 Sept - 7 Sept
found 1 day ago
Return direct flight included
London (LHR) 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 29 Jun 2025
The Ritz-Carlton, Chicago
Downtown Chicago
per person
5 Aug - 10 Aug
found 1 day ago
Return direct flight included
Ankara (ESB) 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 2 Jul 2025
3 Night Adventure holidays in Chicago
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Downtown Chicago
per person
4 Sept - 7 Sept
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
8.8/10 Excellent! (2,274 reviews)
There was an issue with my room and the manager quickly rectified the situation. Swissotel is top notch for customer service!
Reviewed on 5 Jul 2025
4 Night Adventure holidays in Chicago
Price found within the past 48 hours. Click for updated prices.
Hilton Chicago
Downtown Chicago
per person
20 Sept - 24 Sept
found 8 hours ago
Return direct flight included
Port of Spain (POS) to Chicago (ORD)
8.4/10 Very Good! (1,950 reviews)
The property was very nice until we got to the room. The room seemed more dark and dingy. Very expensive for the quality of the room. Staff were extremely nice and the hotel was more central to different parks and modes of transportation.
Reviewed on 2 Jul 2025
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View all tripsTop Adventure Chicago Hotels
Palmer House a Hilton Hotel
17 E Monroe St, Chicago, IL
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 the clean ...
8.2/10 Very Good! (1,772 reviews)
"beautiful hotel, friendly and helpful staff."
Reviewed on 2 Jul 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 Wi-Fi, 3 restaurants and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,000 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 2 Jul 2025
Hyatt Regency Chicago
151 East Wacker Dr, Chicago, IL
Stay at this 4-star eco-certified hotel in Chicago. Enjoy free Wi-Fi, 4 restaurants and 2 bars/lounges. Our guests praise the bar and the helpful staff in their ...
9.2/10 Wonderful! (3,245 reviews)
"Very friendly, top spot, will stay here again!"
Reviewed on 3 Jul 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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.