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 Saint Clair- Magnificent Mile
Downtown Chicago
Price was ￥349,310, price is now ￥320,572 per person
￥320,572
per person
Oct 5 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.2/10 Very Good! (1,709 reviews)
Definitely coming back here again
Reviewed on Sep 5, 2025
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ￥364,457, price is now ￥324,320 per person
￥324,320
per person
Oct 5 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.2/10 Very Good! (2,115 reviews)
I enjoyed the drink voucher at the end of a stressful day, going into a worse one! Staff were lovely.
Reviewed on Sep 4, 2025
Club Quarters Hotel, Central Loop, Chicago
Downtown Chicago
Price was ￥355,835, price is now ￥339,172 per person
￥339,172
per person
Oct 5 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.6/10 Excellent! (3,379 reviews)
Could have been cleaner
Reviewed on Sep 4, 2025
Central Loop Hotel
Downtown Chicago
Price was ￥355,835, price is now ￥340,316 per person
￥340,316
per person
Oct 5 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.6/10 Excellent! (1,839 reviews)
Nice,clean and trendy place to stay at. Self check in and check out if you choose or friendly help front the staff.
Reviewed on Sep 5, 2025
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 ￥305,694, price is now ￥286,301 per person
￥286,301
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,115 reviews)
I enjoyed the drink voucher at the end of a stressful day, going into a worse one! Staff were lovely.
Reviewed on Sep 4, 2025
Club Quarters Hotel, Central Loop, Chicago
Downtown Chicago
Price was ￥304,252, price is now ￥292,808 per person
￥292,808
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.6/10 Excellent! (3,379 reviews)
Could have been cleaner
Reviewed on Sep 4, 2025
4 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 ￥302,152, price is now ￥274,352 per person
￥274,352
per person
Nov 27 - Dec 1
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,115 reviews)
I enjoyed the drink voucher at the end of a stressful day, going into a worse one! Staff were lovely.
Reviewed on Sep 4, 2025
The Whitehall Hotel, BW Premier Collection
Downtown Chicago
Price was ￥306,500, price is now ￥280,302 per person
￥280,302
per person
Nov 27 - Dec 1
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (3,593 reviews)
Excellent location and comfortable clean room. Loved the breakfast in the classy dining room. Very reasonably priced hotel in the heart of Chicago.
Reviewed on Sep 4, 2025
Top Cheap Chicago Hotels
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. ...
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 ...
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 ...
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.
