Romantic Holidays in South Side 2026

Plan, book, travel with confidence
Better together
Save up to RM 3,900 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

Hyatt Regency McCormick Place Chicago

2233 S Martin Luther King Dr Chicago IL

11 min drive from University of Chicago

Stay at this business-friendly hotel in Chicago. Enjoy free Wi-Fi, 3 restaurants and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...

9.2/10 Wonderful! (1,453 reviews)

Couples like: on-site spa services, al fresco dining

Travellers say...

"We stayed 2 nights; the 2nd day no room service; called them & asked them why we didn’t get room service, no clear explanation; after a couple of calls someone had to bring us towels. The first day we got off the elevator on our floor there were dirty towels in the hallway. Not sure how the so-called ..."

Reviewed on 25 Sept 2026

The Wheeler Mansion

2020 South Calumet Avenue Chicago IL

11 min drive from University of Chicago

Stay at this luxury hotel in Chicago. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Soldier Field and Grant Park are located ...

9.6/10 Exceptional! (8 reviews)

"Awesome stay. Close to Soldiers Field."

Reviewed on 3 Sept 2026

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 ...

See all 494 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.