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 $1,339, price is now CA $1,277 per person
CA $1,277
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (1,072 reviews)
Very quiet and clean and very big gym
Reviewed on May 14, 2026
3 Night Cheap holidays 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 $1,339, price is now CA $1,277 per person
CA $1,277
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (1,072 reviews)
Very quiet and clean and very big gym
Reviewed on May 14, 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 $1,690, price is now CA $1,516 per person
CA $1,516
per person
Jul 23 - Jul 27
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
8.2/10 Very Good! (2,703 reviews)
This is always my goto place to stay in the Loop. In the middle of everything. Close to the train. Always clean and never any issues. Staff is great. Quick check-ins. Pastries and coffee next door. What more do you need?
Reviewed on May 21, 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. ...
6.8/10 (1,010 reviews)
"Good clean"
Reviewed on May 20, 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! (1,209 reviews)
"Great restaurants in the area."
Reviewed on May 20, 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.
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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.
