
Chicago Cheap Holidays
Book a Hotel + Flight or Car together to unlock savings
Better together
Save up to €185 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
Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.

Freehand Chicago
Downtown Chicago
per person
21 Aug - 26 Aug
found 16 hours ago
Return flight included
Warsaw (WAW) to Chicago (ORD)
8/10 Very Good! (1,974 reviews)
Great bar and restaurant but rooms need some tlc.
Fixes that would help:
- deep clean carpets
- add sheer curtain behind blackout curtain
- wash curtains
- dust ceiling lamps
- touch up paint on walls
- add garbage cans in bathroom
- add refrigerators in the room
- ensure air conditioning works properly
- bedding and mattress could also be updated
Reviewed on 8 Jul 2025

Central Loop Hotel
Downtown Chicago
per person
21 Aug - 26 Aug
found 16 hours ago
Return flight included
Warsaw (WAW) to Chicago (ORD)
8.6/10 Excellent! (1,778 reviews)
It’s a terrific location and the room was clean and comfortable. It seemed the communication between the checkout staff and house keeping was really lacking, with an expectation that the latter try to figure out when guests had checked out, which made my checkout day very awkward. I’d recommend the hotel if you’re visiting Chicago, but my checkout experience could have been much better.
Reviewed on 7 Jul 2025

Hotel Felix River North/Magnificent Mile
Downtown Chicago
per person
21 Aug - 25 Aug
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.2/10 Very Good! (1,785 reviews)
Love the location of this property as it is close to the train stations. Rooms were clean and had a nice large fridge to hold waters and leftovers. Really cool that the hotel offers coffee and fresh fruit in the lobby in the mornings.
Reviewed on 7 Jul 2025

Club Quarters Hotel, Central Loop, Chicago
Downtown Chicago
per person
21 Aug - 25 Aug
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.6/10 Excellent! (3,362 reviews)
Close to downtown & transportation & walkable to the Lake! On property English pub with great food!
Reviewed on 7 Jul 2025

Price found within the past 48 hours. Click for updated prices.

Hotel Felix River North/Magnificent Mile
Downtown Chicago
per person
21 Aug - 25 Aug
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.2/10 Very Good! (1,785 reviews)
Love the location of this property as it is close to the train stations. Rooms were clean and had a nice large fridge to hold waters and leftovers. Really cool that the hotel offers coffee and fresh fruit in the lobby in the mornings.
Reviewed on 7 Jul 2025


The Whitehall Hotel, BW Premier Collection
Downtown Chicago
per person
21 Aug - 25 Aug
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.2/10 Very Good! (3,440 reviews)
This hotel is perfect. Has the perfect location with the top attractions being 15-20 minute walks from the hotel. Lots of restaurants around a making it easy to eat dinner. Staff was very kind, and early check in fee was reasonable! Would book again when back in Chicago!
Reviewed on 7 Jul 2025

Freehand Chicago
19 East Ohio Street, Chicago, IL
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the bar and the helpful staff in our reviews. ...
7.8/10 Good! (2,039 reviews)
Would stay again
"Wonderful staff! It was also very easy to get around from here. The rooms was very small, but that was expected."
Reviewed on 8 Jul 2025

Travelodge by Wyndham Downtown Chicago
65 E Harrison St, Chicago, IL
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our ...
7/10 Good! (2,236 reviews)
A Great, AffordablePlace to Stay!!
"Excellent stay. Only complaint would be the A/C didn’t cool as well as I wanted. Also no fault of the Hotel, but the traffic and outside atmosphere is extremely loud until about 2am. Other than that, I would stay here again without thinking twice."
Reviewed on 7 Jul 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 WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in ...
7.8/10 Good! (1,530 reviews)
"The room was clean and provided just what I needed -- a bed, a shower, a TV. I only stayed one night. While it is very close to O'Hare airport, the room was quiet. The air-conditioning unit acted like a white noise machine. Still I did not hear the traffic. The parking lot could use a repaving. All ..."
Reviewed on 6 Jul 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.