Central Chicago Adventure Holidays
Book a Adventure Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to £335 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Packages with flights are ATOL protected
Top flight + Adventure hotel deals in Central Chicago
Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North
Downtown Chicago
Price was £1,023, price is now £680 per person
£680
per person
17 Oct - 21 Oct
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (2,052 reviews)
Every staff member were very friendly and helpful. Room was clean and updated. Very easy access to many great restaurants, sites and shopping.
Reviewed on 2 Sep 2025
Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
Price was £1,811, price is now £1,178 per person
£1,178
per person
17 Oct - 21 Oct
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Excellent service with great top notch amenities and a room that has everything you can need away from home. Highly recommend!
Reviewed on 31 Aug 2025
Level Chicago – Old Town
Downtown Chicago
Price was £1,203, price is now £800 per person
£800
per person
17 Oct - 21 Oct
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (343 reviews)
Everything was perfect. Be aware of the expensive it is to park in Chicago.
Reviewed on 2 Sep 2025
The Langham, Chicago
Downtown Chicago
Save 100% on your flight
Price was £2,269, price is now £1,513 per person
£1,513
per person
8 Nov - 15 Nov
found 14 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.
Reviewed on 12 Aug 2025
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 £1,447, price is now £920 per person
£920
per person
13 Nov - 17 Nov
found 13 hours ago
Return direct flight included
Glasgow (GLA) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
Best, very clean, best view, really enjoyed the stay!
Reviewed on 2 Sep 2025
Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
Price was £1,811, price is now £1,178 per person
£1,178
per person
17 Oct - 21 Oct
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Excellent service with great top notch amenities and a room that has everything you can need away from home. Highly recommend!
Reviewed on 31 Aug 2025
The Langham, Chicago
Downtown Chicago
Save 100% on your flight
Price was £2,269, price is now £1,513 per person
£1,513
per person
8 Nov - 15 Nov
found 14 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.
Reviewed on 12 Aug 2025
Don't see what you're looking for?
See all available trips from Glasgow to Central Chicago
View all trips3 Night Adventure holidays in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was £1,518, price is now £1,067 per person
£1,067
per person
10 Oct - 13 Oct
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
8.2/10 Very Good! (2,096 reviews)
The staff from the start were very nice and helpful. The hotel was clean loved the location of the hotel. Will definitely try booking ag this hotel next year
Reviewed on 2 Sep 2025
The Emily Hotel
Downtown Chicago
Price was £1,550, price is now £1,080 per person
£1,080
per person
10 Oct - 13 Oct
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,192 reviews)
Great hotel, especially for the price, nice area, would go back again if I’m in Chicago.
Reviewed on 2 Sep 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was £1,932, price is now £1,376 per person
£1,376
per person
10 Oct - 13 Oct
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
Best, very clean, best view, really enjoyed the stay!
Reviewed on 2 Sep 2025
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.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was £1,633, price is now £1,042 per person
£1,042
per person
17 Oct - 21 Oct
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
Best, very clean, best view, really enjoyed the stay!
Reviewed on 2 Sep 2025
Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
Price was £1,811, price is now £1,178 per person
£1,178
per person
17 Oct - 21 Oct
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Excellent service with great top notch amenities and a room that has everything you can need away from home. Highly recommend!
Reviewed on 31 Aug 2025
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.