South Side Cheap Holidays 2026

Plan, book, travel with confidence
Better together
Save up to NZ$2,400 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place

Top Cheap South Side Hotels

Chinatown Hotel Chicago

214 West 22nd Place Chicago IL

11 min drive from University of Chicago

Stay at this hotel in Chicago. Enjoy free Wi-Fi, a 24-hour front desk and daily housekeeping. Popular attractions Soldier Field and Grant Park are located ...

Best Western Grant Park Hotel

1100 S Michigan Ave Chicago IL

14 min drive from University of Chicago

Stay at this hotel in Chicago. Enjoy free Wi-Fi, breakfast (surcharge) and a 24-hour fitness centre. Our guests praise the helpful staff and the clean rooms ...

8.2/10 Very good! (2,738 reviews)

"Good rate. Clean room. Bed was fine."

Reviewed on 4 Oct 2026

Jaslin Hotel

261 West Cermak Rd Chicago IL

11 min drive from University of Chicago

Stay at this hotel in Chicago. Enjoy free Wi-Fi, a 24-hour fitness centre and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in ...

See all 498 properties in South Side

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.