Chicago Cheap Holidays
Book a Cheap Hotel + Flight or Car together to unlock savings
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
Plan, book, and manage your trip all in one place
Top flight + Cheap hotel deals in Chicago
Price found within the past 48 hours. Click for updated prices.
Club Quarters Hotel, Central Loop, Chicago
Downtown Chicago
per person
5 Sept - 8 Sept
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
8.6/10 Excellent! (3,362 reviews)
Overall, clean and convenient for staying close to downtown/loop. AC needs more maintenance (visible dirt/mold).
Reviewed on 5 Jul 2025
Hotel Felix River North/Magnificent Mile
Downtown Chicago
per person
4 Sept - 7 Sept
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
8.2/10 Very Good! (1,785 reviews)
Their motto “natural and happy” really fits. The staff were pleasant and helpful and the natural touches like natural soaps and cucumber mint infused water made it a comfortable, happy place to stay. An oasis in a hot city.
Reviewed on 4 Jul 2025
Central Loop Hotel
Downtown Chicago
per person
5 Sept - 8 Sept
found 20 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
8.6/10 Excellent! (1,778 reviews)
Overall experience was good from check in to check out. In my room there was a soft cushioned chair that was clearly old and tattered, i didnt use it. I sat in the comfortable desk chair. The charging station was worn out, loose connections made for slow and tedious charging. The room deposit of $100 to be held for 7-10 business days, the industry norm closer to 48 hours.
Reviewed on 4 Jul 2025
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
per person
4 Sept - 7 Sept
found 21 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
8.2/10 Very Good! (1,635 reviews)
it’s a great place to stay, the building is just a little old & you can tell in come places but other than that it’s pretty nice.
Reviewed on 2 Jul 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
per person
4 Sept - 7 Sept
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
8.2/10 Very Good! (1,785 reviews)
Their motto “natural and happy” really fits. The staff were pleasant and helpful and the natural touches like natural soaps and cucumber mint infused water made it a comfortable, happy place to stay. An oasis in a hot city.
Reviewed on 4 Jul 2025
Club Quarters Hotel, Central Loop, Chicago
Downtown Chicago
per person
21 Aug - 24 Aug
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
8.6/10 Excellent! (3,362 reviews)
Overall, clean and convenient for staying close to downtown/loop. AC needs more maintenance (visible dirt/mold).
Reviewed on 5 Jul 2025
Central Loop Hotel
Downtown Chicago
per person
21 Aug - 24 Aug
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
8.6/10 Excellent! (1,778 reviews)
Overall experience was good from check in to check out. In my room there was a soft cushioned chair that was clearly old and tattered, i didnt use it. I sat in the comfortable desk chair. The charging station was worn out, loose connections made for slow and tedious charging. The room deposit of $100 to be held for 7-10 business days, the industry norm closer to 48 hours.
Reviewed on 4 Jul 2025
4 Night Cheap holidays in Chicago
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
per person
20 Sept - 24 Sept
found 6 hours ago
Return direct flight included
Port of Spain (POS) to Chicago (ORD)
8.2/10 Very Good! (1,785 reviews)
Their motto “natural and happy” really fits. The staff were pleasant and helpful and the natural touches like natural soaps and cucumber mint infused water made it a comfortable, happy place to stay. An oasis in a hot city.
Reviewed on 4 Jul 2025
Congress Plaza Hotel
Downtown Chicago
per person
20 Sept - 24 Sept
found 6 hours ago
Return direct flight included
Port of Spain (POS) to Chicago (ORD)
8/10 Very Good! (8,902 reviews)
The history of the hotel is amazing and she might be an old girl with old features but she still shines like a diamond. Plus, the lake side view cannot be beat.
Reviewed on 4 Jul 2025
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
per person
20 Sept - 24 Sept
found 5 hours ago
Return direct flight included
Port of Spain (POS) to Chicago (ORD)
8.2/10 Very Good! (1,635 reviews)
it’s a great place to stay, the building is just a little old & you can tell in come places but other than that it’s pretty nice.
Reviewed on 2 Jul 2025
Don't see what you're looking for?
See all available trips from Port of Spain to Chicago
View all tripsTop 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! (2,022 reviews)
"It was great! My overhead light wasn’t working but it wasn’t that big of a deal. This place is in a really nice spot in River North with lots of places to eat and hang out. It’s really close to public transit too"
Reviewed on 3 Jul 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 ...
7/10 Good! (2,227 reviews)
"Great location. Walking distance to Art Institute, Grant Park and numerous CTA L lines"
Reviewed on 4 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 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! (1,526 reviews)
"Good"
Reviewed on 4 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.
More 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.