Cheap Holidays in South Side 2026

Plan, book, travel with confidence
Better together
Save up to HK$7,200 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

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 ...

5.6/10 (1,006 reviews)

"Honestly, our room was more expensive than what it's worth because there was a big concert in downtown Chicago and everything closer was easily more expensive or in really sketchy areas. It is pretty rundown and need of a deep clean (it smelled like dust and mildew pretty much everywhere but in our ..."

Reviewed on 30 Aug 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 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! (2,750 reviews)

"Staffs were nice and hotel is walking distance to all the popular sites."

Reviewed on 30 Aug 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 ...

9/10 Wonderful! (1,336 reviews)

"This is my second stay at the Jaslin and I cannot recommend this hotel enough. The staff is kind and professional, the rooms have everything we need and are well kept, the view is incredible, and the location is awesome! You can easily walk to anywhere in Chinatown. My friend and I even walked to ..."

Reviewed on 30 Aug 2026

See all 465 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.