South Side Cheap Vacations 2026

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4 Night Cheap vacations in South Side

Price found within the past 48 hours. Click for updated prices.

Best Western Grant Park Hotel

Downtown Chicago

￥288,500

per person

Nov 2 - Nov 6

found 1 day ago

Roundtrip non-stop flight included

Osaka (KIX) to Chicago (ORD)

8.2/10 Very Good! (2,762 reviews)

The hotel is fair.

Reviewed on Aug 29, 2026

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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 WiFi, a 24-hour front desk, and daily housekeeping. Popular attractions Soldier Field and Grant Park are located ...

5.6/10 (1,003 reviews)

"Good location close to the downtown, but requires some improvement in room conditions overall."

Reviewed on Aug 27, 2026

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 WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms ...

8.2/10 Very Good! (2,745 reviews)

"The hotel is fair."

Reviewed on Aug 29, 2026

Jaslin Hotel

261 West Cermak Rd Chicago IL

11 min drive from University of Chicago

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! (1,332 reviews)

"Great food in the area, coffee right next door. Clean hotel. Street parking if it’s not a busy weekend."

Reviewed on Aug 29, 2026

See all 468 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.