South Side Cheap Vacations
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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 $1,469, price is now CA $1,314 per person
CA $1,314
per person
Jul 24 - Jul 27
found 23 hours ago
Roundtrip flight included
Vancouver (YVR) 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 (1,000 reviews)
"We were in town for business and had 2 rooms with several issues, 509 and 511. We had 4 more nights booked but cancelled. The rooms have no way to hang up clothes. Rom 509 tv only got CBS and all other stations said poor signal. The vanity areas need brighter lighting. 511 had a clogged toilet, but ..."
Reviewed on May 21, 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! (1,211 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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