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 £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 Central Chicago
Price found within the past 48 hours. Click for updated prices.
The Chicago Hotel Collection - Magnificent Mile
Downtown Chicago
Price was £930, price is now £780 per person
£780
per person
25 Dec - 30 Dec
found 13 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
8/10 Very good! (2,437 reviews)
Very convenient with a nice room and view
Reviewed on 10 Nov 2026
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View all trips5* Adventure holidays in Central Chicago
Price found within the past 48 hours. Click for updated prices.
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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 £769, price is now £661 per person
£661
per person
15 Jan - 18 Jan
found 13 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
8.4/10 Very good! (3,148 reviews)
Very clean. Had everything that we needed
Reviewed on 10 Nov 2026
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View all trips4 Night Adventure holidays in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Pendry Chicago
Downtown Chicago
Price was £1,320, price is now £1,090 per person
£1,090
per person
26 Dec - 30 Dec
found 10 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)
The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back.
Reviewed on 8 Nov 2026
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View all tripsThings to do
Skydeck Chicago at Willis Tower
£32
per adult
84% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
£30
per adult
94% of travellers recommend
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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.
