South Side Cheap Vacations
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Flight and Cheap hotel deals in South Side
Price found within the past 48 hours. Click for updated prices.
Hyatt Regency McCormick Place Chicago
Near South Side
Price was CA $1,059, price is now CA $991 per person
CA $991
per person
Aug 15 - Aug 17
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.2/10 Wonderful! (1,174 reviews)
It was a pleasure staying at this property. I will return in the future God willing
Reviewed on Jul 6, 2026
4 Night Cheap holidays in South Side
Price found within the past 48 hours. Click for updated prices.
Best Western Grant Park Hotel
Downtown Chicago
Price was CA $1,208, price is now CA $996 per person
CA $996
per person
Aug 10 - Aug 14
found 11 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
8.2/10 Very good! (2,733 reviews)
The room needs some work. The shower poured out the bottom all over the floor in the bathroom, there was some rust and damage and the bed has seen better days. Just seemed a little old. But it was clean and the workers were nice.
Reviewed on Jul 10, 2026
Jaslin Hotel
Chinatown
Price was CA $1,084, price is now CA $1,049 per person
CA $1,049
per person
Aug 18 - Aug 22
found 9 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9/10 Wonderful! (1,237 reviews)
The hotel is convenient for parking and accessing to red line. It takes us easier to go to any place where I want to. The property is clean and room is quietly.
Reviewed on Jul 9, 2026
Cheap Hotels in South Side
Chicago Lake Shore Hotel
4900 S Lake Shore Dr Chicago IL
Stay at this hotel in Chicago. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the overall value in our reviews. ...
7/10 Good! (1,007 reviews)
"Overall value with free parking to me was worth the cost. It would have been nice to at least have an ice machine. We had to walk to the market down the street to purchase."
Reviewed on Jul 10, 2026
Jaslin Hotel
261 West Cermak Rd Chicago IL
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in ...
9/10 Wonderful! (1,248 reviews)
"The hotel is convenient for parking and accessing to red line. It takes us easier to go to any place where I want to. The property is clean and room is quietly."
Reviewed on Jul 9, 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.
Things to do
Wendella's Lake and River Architecture Tour
CA $64
per adult
94% of travellers recommend
Chicago By Night River and Lake Cruise
CA $71
per adult
94% of travellers recommend
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
