Chicago Adventure Holidays
Book a Adventure Hotel + Flight or Car together to unlock savings
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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 Chicago
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Downtown Chicago
Save 100% on your flight
Price was £449, price is now £312 per person
£312
per person
25 Sept - 27 Sept
found 15 hours ago
Return direct flight included
Baltimore (BWI) to Chicago (ORD)
8.8/10 Excellent! (2,544 reviews)
Location, staff, and room size was everthing as advertised.
Reviewed on 20 Aug 2025
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was £1,730, price is now £1,041 per person
£1,041
per person
20 Sept - 27 Sept
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,033 reviews)
Loved the atmosphere and friendly atmosphere
Reviewed on 18 Aug 2025
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was £1,580, price is now £984 per person
£984
per person
20 Sept - 27 Sept
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (3,359 reviews)
Shawn at the front desk was awesome. It was our first time in Chicago and we loved staying at LondonHouse!
Reviewed on 19 Aug 2025
The Royal Sonesta Chicago River North
Downtown Chicago
Save 100% on your flight
Price was £1,263, price is now £806 per person
£806
per person
20 Sept - 27 Sept
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,980 reviews)
Friendly staff, clean and comfortable, convenient location
Reviewed on 20 Aug 2025
Radisson Blu Aqua Hotel Chicago
Downtown Chicago
Save 100% on your flight
Price was £1,661, price is now £1,126 per person
£1,126
per person
20 Sept - 27 Sept
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
8.4/10 Very Good! (1,586 reviews)
The hotel is a nice hotel. The business center need to upgrade the printing facility and they need to have paper available.
The swimming pool needs to be clean at least three times a day
Reviewed on 19 Aug 2025
5* Adventure holidays in Chicago
Price found within the past 48 hours. Click for updated prices.
Four Seasons Hotel Chicago
Downtown Chicago
Price was £2,315, price is now £2,019 per person
£2,019
per person
24 Oct - 28 Oct
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
I loved it all. Brought my 5 year old grandson Mateo and they catered to him including their kid room key card , a treasure chest choice, a hat and stuffed animal and his own kid sized robe. He spilled some food in restaurant and we apologized profusely, but they waved it off saying they were family friendly. Loved the pool, loved the hot tub, loved how kind and friendly staff was
Reviewed on 14 Aug 2025
The Peninsula Chicago
Downtown Chicago
Save 100% on your flight
Price was £2,866, price is now £2,160 per person
£2,160
per person
20 Sept - 27 Sept
found 2 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.8/10 Exceptional! (1,004 reviews)
The most beautiful hotel !
Reviewed on 17 Aug 2025
3 Night Adventure holidays in Chicago
Price found within the past 48 hours. Click for updated prices.
InterContinental Chicago Magnificent Mile by IHG
Downtown Chicago
Price was £1,356, price is now £1,127 per person
£1,127
per person
10 Oct - 13 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (2,173 reviews)
We were charged for 3 bottles of wine from the in-room bar even though we didn’t touch one item in it. And we were never sent a copy of the check out invoice when we requested it be sent via email, which was confirmed during check out. Once we received the invoice, after calling the hotel, we found the erroneous wine charge and were quite upset. After calling and expressing our concern and disappointment, we received a full refund of the wine bottle charges very promptly. Not impressed that we were charged for something we did not use but were satisfied with the final outcome and refund. Although the hotel was otherwise excellent, we will not stay there again because of this.
Reviewed on 20 Aug 2025
Four Seasons Hotel Chicago
Downtown Chicago
Price was £1,840, price is now £1,497 per person
£1,497
per person
10 Oct - 13 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
I loved it all. Brought my 5 year old grandson Mateo and they catered to him including their kid room key card , a treasure chest choice, a hat and stuffed animal and his own kid sized robe. He spilled some food in restaurant and we apologized profusely, but they waved it off saying they were family friendly. Loved the pool, loved the hot tub, loved how kind and friendly staff was
Reviewed on 14 Aug 2025
4 Night Adventure holidays in Chicago
Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North
Downtown Chicago
Price was £1,596, price is now £1,250 per person
£1,250
per person
24 Oct - 28 Oct
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,980 reviews)
Friendly staff, clean and comfortable, convenient location
Reviewed on 20 Aug 2025
Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
Price was £1,997, price is now £1,582 per person
£1,582
per person
24 Oct - 28 Oct
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
One of the tvs didnt work, and neither did the room phone. Dislike the texting communication, and having to go thru 3rd party just to call front desk.
Reviewed on 17 Aug 2025
Top Adventure Chicago Hotels
Palmer House a Hilton Hotel
17 E Monroe St, Chicago, IL
Stay at this spa hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge) and a 24-hour health club. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (1,871 reviews)
"It’s a beautiful hotel with lovely staff. The beds were very comfy but the pillows have no neck support. We loved how close it was to Millennium park and how walkable the area was for finding dining options and seeing the sights. It’s only about one city block from the Art Institute and we got to ..."
Reviewed on 18 Aug 2025
Hyatt Regency McCormick Place Chicago
2233 S Martin Luther King Dr, Chicago, IL
Stay at this 4-star eco-certified 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! (1,002 reviews)
"Very good"
Reviewed on 15 Aug 2025
Hyatt Regency Chicago
151 East Wacker Dr, Chicago, IL
Stay at this 4-star eco-certified hotel in Chicago. Enjoy free Wi-Fi, 4 restaurants and 2 bars/lounges. Our guests praise the bar and the helpful staff in their ...
9.2/10 Wonderful! (3,311 reviews)
"Great"
Reviewed on 20 Aug 2025
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.