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
per person
Aug 28 - Sep 1
found 8 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
8.2/10 Very Good! (1,842 reviews)
The hotel Felix exceeded my expectations. I was pleasantly surprised. The room was clean and very nice. I highly recommend the Hoel Felix.
Reviewed on Jul 20, 2025
River Hotel
Downtown Chicago
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
8.8/10 Excellent! (4,346 reviews)
This hotel is right on the river next to Michigan Ave. We were able to walk to most of the places we wanted to see. The staff provided a list of restaurants and nightspots that was very helpful.
Reviewed on Jul 20, 2025
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
per person
Sep 30 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.2/10 Very Good! (1,645 reviews)
Dinning on the property. Parking and ease of retrieving our vehicle when needed. Convenient to restaurants and shopping.
Reviewed on Jul 21, 2025
Club Quarters Hotel, Central Loop, Chicago
Downtown Chicago
per person
Aug 28 - Sep 1
found 8 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
8.6/10 Excellent! (3,357 reviews)
i paid for a suite and the room was the smallest room ive ever stayed at in a hotel
Reviewed on Jul 21, 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
per person
Aug 31 - Sep 3
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
8.2/10 Very Good! (1,842 reviews)
The hotel Felix exceeded my expectations. I was pleasantly surprised. The room was clean and very nice. I highly recommend the Hoel Felix.
Reviewed on Jul 20, 2025
River Hotel
Downtown Chicago
per person
Aug 31 - Sep 3
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
8.8/10 Excellent! (4,346 reviews)
This hotel is right on the river next to Michigan Ave. We were able to walk to most of the places we wanted to see. The staff provided a list of restaurants and nightspots that was very helpful.
Reviewed on Jul 20, 2025
Club Quarters Hotel, Central Loop, Chicago
Downtown Chicago
per person
Aug 31 - Sep 3
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
8.6/10 Excellent! (3,357 reviews)
i paid for a suite and the room was the smallest room ive ever stayed at in a hotel
Reviewed on Jul 21, 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
per person
Aug 28 - Sep 1
found 8 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
8.2/10 Very Good! (1,842 reviews)
The hotel Felix exceeded my expectations. I was pleasantly surprised. The room was clean and very nice. I highly recommend the Hoel Felix.
Reviewed on Jul 20, 2025
River Hotel
Downtown Chicago
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
8.8/10 Excellent! (4,346 reviews)
This hotel is right on the river next to Michigan Ave. We were able to walk to most of the places we wanted to see. The staff provided a list of restaurants and nightspots that was very helpful.
Reviewed on Jul 20, 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. ...
7.8/10 Good! (2,090 reviews)
"A"
Reviewed on Jul 20, 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 ...
7/10 Good! (2,248 reviews)
"Everything good, a little dated but clean."
Reviewed on Jul 18, 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! (1,549 reviews)
"I'm going through a difficult time right now and it gives me and my children a safe place."
Reviewed on Jul 15, 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.