Chicago Cheap Holidays
Book a Cheap Hotel + Flight or Car together to unlock savings
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Save up to £335 when you book a flight and hotel together*
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With over 300,000 hotels worldwide, it's easy to create a perfect package
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Packages with flights are ATOL protected
Top flight + Cheap hotel deals in Chicago
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was £1,011, price is now £684 per person
£684
per person
20 Sept - 27 Sept
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
8.2/10 Very Good! (1,991 reviews)
Great spot, good location, nice rooms.
Reviewed on 20 Aug 2025
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
Price was £1,377, price is now £1,061 per person
£1,061
per person
2 Oct - 9 Oct
found 1 hour ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
8.2/10 Very Good! (1,684 reviews)
The rooms are small, but sufficient for a tourist to Chicago. If you come to Chicago you really only need a good bed and a place to sleep comfortably. There is so much to do close to this hotel it is all you need.
Reviewed on 20 Aug 2025
River Hotel
Downtown Chicago
Price was £960, price is now £755 per person
£755
per person
20 Sept - 27 Sept
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
8.8/10 Excellent! (4,488 reviews)
Fantastic front desk experience. TOPS!! We used the expensive valet parking, but I would use it again. It makes things so much easier.
Reviewed on 20 Aug 2025
Central Loop Hotel
Downtown Chicago
Price was £1,347, price is now £1,205 per person
£1,205
per person
12 Oct - 19 Oct
found 1 hour ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
8.6/10 Excellent! (1,814 reviews)
Location was great and checking in and out was very easy. The staff was helpful too.
Reviewed on 18 Aug 2025
3 Night Cheap holidays in Chicago
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was £1,464, price is now £1,008 per person
£1,008
per person
10 Oct - 13 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.2/10 Very Good! (1,991 reviews)
Great spot, good location, nice rooms.
Reviewed on 20 Aug 2025
River Hotel
Downtown Chicago
Price was £1,215, price is now £962 per person
£962
per person
10 Oct - 13 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.8/10 Excellent! (4,488 reviews)
Fantastic front desk experience. TOPS!! We used the expensive valet parking, but I would use it again. It makes things so much easier.
Reviewed on 20 Aug 2025
4 Night Cheap holidays in Chicago
Price found within the past 48 hours. Click for updated prices.
River Hotel
Downtown Chicago
Price was £1,251, price is now £1,022 per person
£1,022
per person
9 Oct - 13 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.8/10 Excellent! (4,488 reviews)
Fantastic front desk experience. TOPS!! We used the expensive valet parking, but I would use it again. It makes things so much easier.
Reviewed on 20 Aug 2025
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was £1,552, price is now £1,100 per person
£1,100
per person
9 Oct - 13 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.2/10 Very Good! (1,991 reviews)
Great spot, good location, nice rooms.
Reviewed on 20 Aug 2025
Ohio House Motel
Downtown Chicago
Price was £1,298, price is now £1,121 per person
£1,121
per person
9 Oct - 13 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,012 reviews)
Pros: great location- easy to get to. Parking - though there is a $39 charge, relatively quiet - you’re in a motel in the middle of a huge city, Schneider Deli - the best deli in Chicago on the other side of the motel’s office. Fantastic breakfast!
Cons: the price of parking.
A great option to stay in Chicago if you have a car.
Reviewed on 16 Aug 2025
Top Cheap Chicago Hotels
Freehand Chicago
19 East Ohio Street, Chicago, IL
Stay at this 4-star hotel in Chicago. Enjoy free Wi-Fi, room service and a 24-hour fitness centre. Our guests praise the bar and the helpful staff in their reviews. ...
7.8/10 Good! (2,216 reviews)
"Awesome, unique spot in downtown. Great staff and drinks."
Reviewed on 18 Aug 2025
Travelodge by Wyndham Downtown Chicago
65 E Harrison St, Chicago, IL
Stay at this hotel in Chicago. Enjoy free Wi-Fi, a 24-hour front desk and daily housekeeping. Our guests praise the helpful staff and the clean rooms in their ...
7.2/10 Good! (2,287 reviews)
"I stayed at the Travelodge by Wyndham Downtown Chicago for three nights with my partner while visiting the city. I’ll admit I was a little nervous when booking after reading some mixed reviews, but for the price, I decided to give it a shot. I was pleasantly surprised when we arrived and got to our ..."
Reviewed on 14 Aug 2025
Motel 6 Elk Grove Village, IL - O'Hare
2881 Touhy Ave, Elk Grove Village, IL
Stay at this motel in Elk Grove Village. Enjoy free Wi-Fi, free parking and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in ...
7.8/10 Good! (1,595 reviews)
"Fulfilled everything I needed it to be. Wifi was down, but that was fine."
Reviewed on 17 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.