Chicago Adventure Holidays
Book a Adventure Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to £750 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.
Swissotel - Chicago
Downtown Chicago
Save 100% on your flight
Price was £2,416, price is now £1,570 per person
£1,570
per person
31 Jul - 4 Aug
found 22 hours ago
Return direct flight included
Glasgow (GLA) to Chicago (ORD)
9/10 Wonderful! (3,303 reviews)
This property has a great location. The hotel was really clean! We enjoyed the bar atmosphere, and we had a delicious appetizer! I will highly recommend this location for a great getaway for couples! Page at the front desk and Prudencia in housekeeping were amazing!
Reviewed on 13 May 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was £1,966, price is now £1,454 per person
£1,454
per person
31 Jul - 4 Aug
found 22 hours ago
Return direct flight included
Glasgow (GLA) to Chicago (ORD)
9.4/10 Exceptional! (3,692 reviews)
Great location.
Very friendly and helpful staff.
Reviewed on 13 May 2026
InterContinental Chicago Magnificent Mile by IHG
Downtown Chicago
Price was £1,122, price is now £1,006 per person
£1,006
per person
1 Jul - 5 Jul
found 6 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (3,039 reviews)
Absolutely great trip. So glad I booked with Expedia. Made everything very easy and convenient
Reviewed on 14 May 2026
5* Adventure holidays in Chicago
Price found within the past 48 hours. Click for updated prices.
Four Seasons Hotel Chicago
Downtown Chicago
Price was £2,416, price is now £2,116 per person
£2,116
per person
31 Jul - 4 Aug
found 22 hours ago
Return direct flight included
Glasgow (GLA) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Loved our suite- gorgeous views! Great service and excellent location
Reviewed on 8 May 2026
4 Night Adventure holidays in Chicago
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Downtown Chicago
Price was £1,238, price is now £991 per person
£991
per person
1 Jul - 5 Jul
found 6 hours ago
Return flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (3,303 reviews)
This property has a great location. The hotel was really clean! We enjoyed the bar atmosphere, and we had a delicious appetizer! I will highly recommend this location for a great getaway for couples! Page at the front desk and Prudencia in housekeeping were amazing!
Reviewed on 13 May 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was £1,242, price is now £1,041 per person
£1,041
per person
1 Jul - 5 Jul
found 6 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (3,692 reviews)
Great location.
Very friendly and helpful staff.
Reviewed on 13 May 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 ...
8.6/10 Excellent! (2,446 reviews)
Beautiful hotel , we had a wonderful stay
Reviewed on 13 May 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 ...
9.2/10 Wonderful! (1,072 reviews)
Great stay!
Reviewed on 11 May 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 ...
9.4/10 Exceptional! (3,514 reviews)
Amazing
Reviewed on 12 May 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.
