Central Chicago Adventure Holidays
Book a Adventure Hotel + Flight or Car together to unlock savings
Photo by Phil Ostroff
- 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 Central Chicago
Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was £1,911, price is now £1,336 per person
£1,336
per person
3 Jun - 9 Jun
found 15 hours ago
Return flight included
London (LON) to Chicago (ORD)
8.6/10 Excellent! (2,076 reviews)
Very nice & clean hotel and near the Bean and shops are walkable.
Reviewed on 3 Mar 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was £2,285, price is now £1,548 per person
£1,548
per person
3 Jun - 9 Jun
found 15 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (2,385 reviews)
The room so clean with a beautiful view!
Reviewed on 13 Mar 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was £2,635, price is now £1,828 per person
£1,828
per person
3 Jun - 9 Jun
found 13 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,844 reviews)
Room was perfect/staff was great
Reviewed on 12 Mar 2026
Don't see what you're looking for?
See all available trips from London to Central Chicago
View all trips5* Adventure holidays in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was £2,635, price is now £1,828 per person
£1,828
per person
3 Jun - 9 Jun
found 13 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,844 reviews)
Room was perfect/staff was great
Reviewed on 12 Mar 2026
Don't see what you're looking for?
See all available trips from London to Central Chicago
View all trips4 Night Adventure holidays in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was £1,431, price is now £989 per person
£989
per person
30 Apr - 4 May
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (3,438 reviews)
Good breakfast, excellent service, unfortunately, they don't have microwave service to heat food
Reviewed on 13 Mar 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was £1,665, price is now £1,327 per person
£1,327
per person
30 Apr - 4 May
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,844 reviews)
Room was perfect/staff was great
Reviewed on 12 Mar 2026
Don't see what you're looking for?
See all available trips from London to Central Chicago
View all tripsMore holidays you might like
* 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.
