South Side Romantic Vacations 2026

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Top Romantic South Side Hotels

Hyatt Regency McCormick Place Chicago

2233 S Martin Luther King Dr Chicago IL

11 min drive from University of Chicago

Al fresco dining and premium mattresses await at this romantic hotel, which also offers luxury bedding and a lakeside location.

9.2/10 Wonderful! (1,453 reviews)

Couples like: onsite spa services, al fresco dining

Travelers 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 Sep 25, 2026

The Wheeler Mansion

2020 South Calumet Avenue Chicago IL

11 min drive from University of Chicago

Ready for a romantic getaway? You are sure to enjoy the garden, lobby fireplace, and premium mattresses at this boutique hotel. You'll also appreciate the luxury ...

9.6/10 Exceptional! (8 reviews)

"Awesome stay. Close to Soldiers Field."

Reviewed on Sep 3, 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 WiFi, a 24-hour front desk, and daily housekeeping. Popular attractions Soldier Field and Grant Park are located ...

See all 491 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.