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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! (1,057 reviews)

Couples like: onsite spa services, al fresco dining

Travelers say...

The room and staff were great

Reviewed on 2026/1/6

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 2025/6/23

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 (1,001 reviews)

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Reviewed on 2026/1/15

See all 464 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.