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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 ...

9/10 Wonderful! (1,065 reviews)

Couples like: onsite spa services, al fresco dining

Travelers say...

Very nice Hotel. Nice room and view!! The staff were friendly. We will be back to stay at this Hotel.

Reviewed on Jan 31, 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 ...

9/10 Wonderful! (4 reviews)

A unique place to stay near the convention centre.

Reviewed on Jun 23, 2025

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 Millennium Park are located ...

5.4/10 (1,002 reviews)

Great rooms With upgraded, Recently Renovated!

Reviewed on Feb 2, 2026

See all 474 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.