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 ￥295,941, price is now ￥248,074 per person
￥248,074
per person
May 12 - May 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.2/10 Very Good! (2,573 reviews)
the staff was very friendly and helpful in a number of areas. The coffee was good each morning and the food as well.
The location is excellent and i would go back.
Reviewed on Mar 4, 2026
Freehand Chicago
Downtown Chicago
Price was ￥446,622, price is now ￥388,074 per person
￥388,074
per person
May 28 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8/10 Very Good! (2,785 reviews)
Loved my stay. The cushions for the couch in the bedroom could’ve used a good wash. It’s exacting in the walking distance of everything which I was surprised about. I will be staying again.
Reviewed on Mar 10, 2026
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
Price was ￥343,425, price is now ￥307,522 per person
￥307,522
per person
Jun 5 - Jun 9
found 3 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.4/10 Very Good! (1,854 reviews)
The staff was kind, the room is clean, overall awesome! I would recommend
Reviewed on Mar 11, 2026
River Hotel
Downtown Chicago
Price was ￥287,052, price is now ￥260,870 per person
￥260,870
per person
May 12 - May 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.8/10 Excellent! (5,027 reviews)
The River Hotel – 75 Walker Street, Chicago
A wonderful experience overall! As a solo traveler attending a conference, the accommodations were comfortable and the staff was exceptionally friendly and helpful. The hotel itself is a beautiful historical landmark, ideally located within walking distance of major attractions, shops, and entertainment. Getting to and from O’Hare airport was seamless via train, taxi, or rideshare. Highly recommend!
Reviewed on Mar 11, 2026
Club Quarters Hotel, Central Loop, Chicago
Downtown Chicago
Price was ￥286,555, price is now ￥260,496 per person
￥260,496
per person
May 12 - May 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.8/10 Excellent! (3,428 reviews)
Clean room, courteous staff and excellent facilities - meeting room and coffee machine...only demerit was the lack of a bureau in the room (vs a mini-bureau in the closet).
Reviewed on Mar 2, 2026
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 ￥275,356, price is now ￥263,542 per person
￥263,542
per person
May 15 - May 19
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
7.4/10 Good! (1,280 reviews)
Staff was very cordial and inviting.
Reviewed on Mar 10, 2026
Regal Inn - Chicago O'Hare Airport
Price was ￥249,588, price is now ￥244,281 per person
￥244,281
per person
May 15 - May 19
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8/10 Very Good! (1,001 reviews)
It was clean but not spotless. Great staff though. Always super helpful and nice. The rooms just need a bit of updating.
Reviewed on Feb 28, 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! (1,861 reviews)
Everything was fine but I didn't get room service for 4 days.
Reviewed on Mar 11, 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. ...
8/10 Very Good! (2,799 reviews)
Loved my stay. The cushions for the couch in the bedroom could’ve used a good wash. It’s exacting in the walking distance of everything which I was surprised about. I will be staying again.
Reviewed on Mar 10, 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! (2,522 reviews)
The staff were very friendly and attentive. Perfect location to go to and from the busy part of downtown Chicago. It was nice going back to quiet after the bustle :)
Reviewed on Mar 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.
