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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

Book a stay at this romantic hotel, featuring in-room massages and al fresco dining. Couples will appreciate the premium mattresses, luxury bedding, and 2 ...

9.2/10 Wonderful! (1,068 reviews)

Couples like: onsite spa services, al fresco dining

Travelers say...

Clean toom beautiful views

Reviewed on Mar 3, 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 (1,001 reviews)

Clean

Reviewed on Mar 7, 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.