
Chicago Cheap Vacations
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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 ¥227,471, price is now ¥200,780 per person
¥200,780
per person
Mar 26 - Mar 30
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,365 reviews)
I liked the hotel. The staff was very courteous and friendly. The room was cute. The location is fantastic.
Reviewed on Jan 20, 2026

Central Loop Hotel
Downtown Chicago
Price was ¥233,949, price is now ¥208,878 per person
¥208,878
per person
Apr 15 - Apr 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.6/10 Excellent! (1,896 reviews)
Everything was good, they were so nice and helpful. Even when our room heat went out they handled it quickly and let us get a new room ! They even upgraded our room
Reviewed on Jan 24, 2026

River Hotel
Downtown Chicago
Price was ¥243,366, price is now ¥221,452 per person
¥221,452
per person
Apr 15 - Apr 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (4,800 reviews)
We stayed here last summer and really liked this place, so we chose here again.
Besides, the staff is kind, nice, and welcoming; the room is spotless; everything is clean; and the location is super convenient. Easy to check-in, water filling station on each floor, and check-out time is noon (most places are at 11am). We also love that the Nespresso coffee machine is in the room. You can start the morning with good coffee in the room. Though there is a coffee station on the second floor 24 hours. We would choose this place again next time. :)
Reviewed on Jan 24, 2026

Hotel Saint Clair- Magnificent Mile
Downtown Chicago
Price was ¥226,826, price is now ¥208,457 per person
¥208,457
per person
Mar 26 - Mar 30
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (1,769 reviews)
Very clean and comfortable room. I had a nice time at the Saint Clair Hotel.
Reviewed on Jan 22, 2026

Club Quarters Hotel, Central Loop, Chicago
Downtown Chicago
Price was ¥229,760, price is now ¥215,398 per person
¥215,398
per person
Mar 26 - Mar 30
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (3,289 reviews)
Everything was great the parking was very difficult and not so convenient to the area.
Reviewed on Jan 19, 2026
3 Night Cheap vacations in Chicago
Price found within the past 48 hours. Click for updated prices.

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ¥234,784, price is now ¥216,552 per person
¥216,552
per person
Mar 16 - Mar 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
8.2/10 Very Good! (2,365 reviews)
I liked the hotel. The staff was very courteous and friendly. The room was cute. The location is fantastic.
Reviewed on Jan 20, 2026

River Hotel
Downtown Chicago
Price was ¥237,668, price is now ¥227,336 per person
¥227,336
per person
Mar 16 - Mar 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
8.8/10 Excellent! (4,800 reviews)
We stayed here last summer and really liked this place, so we chose here again.
Besides, the staff is kind, nice, and welcoming; the room is spotless; everything is clean; and the location is super convenient. Easy to check-in, water filling station on each floor, and check-out time is noon (most places are at 11am). We also love that the Nespresso coffee machine is in the room. You can start the morning with good coffee in the room. Though there is a coffee station on the second floor 24 hours. We would choose this place again next time. :)
Reviewed on Jan 24, 2026

Club Quarters Hotel, Central Loop, Chicago
Downtown Chicago
Price was ¥234,500, price is now ¥224,873 per person
¥224,873
per person
Mar 16 - Mar 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
8.8/10 Excellent! (3,289 reviews)
Everything was great the parking was very difficult and not so convenient to the area.
Reviewed on Jan 19, 2026
4 Night Cheap vacations in Chicago
Price found within the past 48 hours. Click for updated prices.

SureStay Plus Hotel by Best Western Chicago Lombard
Highland Hills
Price was ¥197,997, price is now ¥187,325 per person
¥187,325
per person
Apr 15 - Apr 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (2,375 reviews)
I enjoyed my stay only regret was no hot tub or pool.
Reviewed on Jan 24, 2026

River Hotel
Downtown Chicago
Price was ¥243,366, price is now ¥221,452 per person
¥221,452
per person
Apr 15 - Apr 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (4,800 reviews)
We stayed here last summer and really liked this place, so we chose here again.
Besides, the staff is kind, nice, and welcoming; the room is spotless; everything is clean; and the location is super convenient. Easy to check-in, water filling station on each floor, and check-out time is noon (most places are at 11am). We also love that the Nespresso coffee machine is in the room. You can start the morning with good coffee in the room. Though there is a coffee station on the second floor 24 hours. We would choose this place again next time. :)
Reviewed on Jan 24, 2026

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ¥319,336, price is now ¥294,490 per person
¥294,490
per person
Mar 16 - Mar 20
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,365 reviews)
I liked the hotel. The staff was very courteous and friendly. The room was cute. The location is fantastic.
Reviewed on Jan 20, 2026
Top Cheap Chicago Hotels

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! (1,778 reviews)
The staff is really helpful and informative plus I love the fact that they have a laundry room and vending machines.
Reviewed on Jan 19, 2026

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! (2,703 reviews)
Best staff best place in the city for your money if you’re willing to share your space and meet new people!
Reviewed on Jan 17, 2026

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 ...
7.4/10 Good! (2,503 reviews)
Only thing I would change is add mini fridges to the rooms.
Reviewed on Jan 10, 2026
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.
