Chicago Adventure Holidays
Book a Adventure Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to £335 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 easyPackages with flights are ATOL protected
Top flight + Adventure hotel deals in Chicago
Price found within the past 48 hours. Click for updated prices.
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was £1,834, price is now £1,141 per person
£1,141
per person
30 Apr - 6 May
found 19 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Muriel at the front desk was extremely helpful and courteous, wonderful historic art deco building right on Michigan Ave., great location and views, really nice, spacious and clean room. Chateau Carbide on the 24th floor is definitely worth checking out, nice cozy areas to hang out, sit on a couch and have a drink while enjoying great views of the city. We also got a free ride from the hotel to the Shedd Aquarium.
Reviewed on 31 Jan 2026
Swissotel - Chicago
Downtown Chicago
Price was £1,418, price is now £1,193 per person
£1,193
per person
20 Apr - 24 Apr
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9/10 Wonderful! (2,947 reviews)
Clean room and location but the Palm restaurant food was horrible. It is not recommended.!
Reviewed on 7 Feb 2026
5* Adventure holidays in Chicago
Price found within the past 48 hours. Click for updated prices.
3 Night Adventure holidays in Chicago
Price found within the past 48 hours. Click for updated prices.
Kinzie Hotel
Downtown Chicago
Price was £873, price is now £795 per person
£795
per person
20 Mar - 23 Mar
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,993 reviews)
The room was incredibly clean and had a great view! The staff was so nice and Deandre was such a wonderful host at checkout. Thank you for the amazing stay!
Reviewed on 29 Jan 2026
Pendry Chicago
Downtown Chicago
Price was £1,037, price is now £892 per person
£892
per person
20 Mar - 23 Mar
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Muriel at the front desk was extremely helpful and courteous, wonderful historic art deco building right on Michigan Ave., great location and views, really nice, spacious and clean room. Chateau Carbide on the 24th floor is definitely worth checking out, nice cozy areas to hang out, sit on a couch and have a drink while enjoying great views of the city. We also got a free ride from the hotel to the Shedd Aquarium.
Reviewed on 31 Jan 2026
The Royal Sonesta Chicago Downtown
Downtown Chicago
Price was £925, price is now £822 per person
£822
per person
20 Mar - 23 Mar
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (3,062 reviews)
Excellent room and really great location. Stayed during the snowstorm and it was still easy to get around. Helpful friendly staff team. Note: closest EL Train station (State/Lake) closed for redevelopment till 2029.
Reviewed on 8 Feb 2026
4 Night Adventure holidays in Chicago
Price found within the past 48 hours. Click for updated prices.
Pendry Chicago
Downtown Chicago
Price was £1,379, price is now £1,102 per person
£1,102
per person
4 May - 8 May
found 17 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Muriel at the front desk was extremely helpful and courteous, wonderful historic art deco building right on Michigan Ave., great location and views, really nice, spacious and clean room. Chateau Carbide on the 24th floor is definitely worth checking out, nice cozy areas to hang out, sit on a couch and have a drink while enjoying great views of the city. We also got a free ride from the hotel to the Shedd Aquarium.
Reviewed on 31 Jan 2026
Swissotel - Chicago
Downtown Chicago
Price was £1,418, price is now £1,193 per person
£1,193
per person
20 Apr - 24 Apr
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9/10 Wonderful! (2,947 reviews)
Clean room and location but the Palm restaurant food was horrible. It is not recommended.!
Reviewed on 7 Feb 2026
Top Adventure Chicago Hotels
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
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 and the ...
8.4/10 Very Good! (2,280 reviews)
Clean room, checking in was super easy. Hotel is beautiful and so classy.
Reviewed on 7 Feb 2026
Hyatt Regency McCormick Place Chicago
2233 S Martin Luther King Dr Chicago IL
Stay at this business-friendly 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! (1,065 reviews)
Very nice Hotel. Nice room and view!! The staff were friendly. We will be back to stay at this Hotel.
Reviewed on 31 Jan 2026
Hyatt Regency Chicago
151 East Wacker Dr Chicago IL
Stay at this business-friendly hotel in Chicago. Enjoy free Wi-Fi, 4 restaurants and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
9.2/10 Wonderful! (3,459 reviews)
Clean room, professional staff, and great location
Reviewed on 3 Feb 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.
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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.
