
Chicago Cheap Vacations
Book a Cheap Hotel + Flight or Car together to unlock savings
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- Better togetherSave up to ¥45,448 when you book a flight and hotel together*
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Top Cheap vacation packages in Chicago
Price found within the past 48 hours. Click for updated prices.


Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ¥366,065, price is now ¥264,068 per person
¥264,068
per person
Jan 17 - Jan 21
found 19 hours ago
Roundtrip flight included
Kitakyushu (KKJ) to Chicago (ORD)
8.2/10 Very Good! (2,365 reviews)
Great welcome. Room looks good.
Reviewed on Dec 3, 2025

River Hotel
Downtown Chicago
Price was ¥165,379, price is now ¥148,512 per person
¥148,512
per person
Feb 19 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (4,800 reviews)
Ron helped us with luggage storage and then check in. Excellent customer service!! So far our stay has been great!!
Reviewed on Dec 4, 2025

Club Quarters Hotel, Central Loop, Chicago
Downtown Chicago
Price was ¥158,075, price is now ¥150,154 per person
¥150,154
per person
Feb 4 - Feb 8
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (3,289 reviews)
Clean and comfy room with great location
Reviewed on Dec 3, 2025

Central Loop Hotel
Downtown Chicago
Price was ¥158,075, price is now ¥150,154 per person
¥150,154
per person
Feb 4 - Feb 8
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.6/10 Excellent! (1,896 reviews)
This was our second time staying here. It's clean, cheap, and in a convenient location.
Reviewed on Dec 2, 2025
4 Night Cheap vacations in Chicago
Price found within the past 48 hours. Click for updated prices.

Country Inn & Suites by Radisson, Chicago O'Hare South, IL
Price was ¥160,770, price is now ¥139,206 per person
¥139,206
per person
Feb 19 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
7.2/10 Good! (1,168 reviews)
The staff was great, the hotel was outdated, and the free breakfast tasted microwaved. But hey for the price I got the room for I can’t be too mad. Only real disappointment was the pool area that looks unkept. Not to mention it reeks of wet dog when you enter and no towels were available. I tired out the jacuzzi for 15mins I couldn’t stand the smell anymore
Reviewed on Dec 3, 2025

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ¥366,065, price is now ¥264,068 per person
¥264,068
per person
Jan 17 - Jan 21
found 19 hours ago
Roundtrip flight included
Kitakyushu (KKJ) to Chicago (ORD)
8.2/10 Very Good! (2,365 reviews)
Great welcome. Room looks good.
Reviewed on Dec 3, 2025

Top Cheap Chicago Hotels

Freehand Chicago
19 East Ohio Street Chicago IL
Stay at this hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...
7.8/10 Good! (2,621 reviews)
Habitación pequeña pero muy confortable, baño completo y bien equipado, excelente ubicación del hotel.
Reviewed on Nov 29, 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 ...
7.2/10 Good! (2,485 reviews)
Yes
Reviewed on Nov 29, 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! (1,716 reviews)
Room is pretty clean. Most of the staff is friendly except one front desk woman.
Reviewed on Nov 30, 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.
