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! (1,256 reviews)

Couples like: onsite spa services, al fresco dining

Travelers say...

"Very nice, new room with excellent views of the city and Lake. Stayed for a concert at Soldier Field and it was an easy walk. Would stay again."

Reviewed on Aug 11, 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 ...

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 (1,000 reviews)

"I have no comment"

Reviewed on Aug 7, 2026

See all 460 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.