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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

Stay at this business-friendly hotel in Chicago. Enjoy free Wi-Fi, 3 restaurants and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...

9/10 Wonderful! (1,063 reviews)

Couples like: on-site spa services, al fresco dining

Travellers say...

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

Reviewed on 31 Jan 2026

The Wheeler Mansion

2020 South Calumet Avenue Chicago IL

11 min drive from University of Chicago

Stay at this luxury hotel in Chicago. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Soldier Field and Millennium Park are located ...

9/10 Wonderful! (4 reviews)

A unique place to stay near the convention centre.

Reviewed on 23 Jun 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 Wi-Fi, a 24-hour front desk and daily housekeeping. Popular attractions Soldier Field and Millennium Park are located ...

5.4/10 (1,000 reviews)

Great rooms With upgraded, Recently Renovated!

Reviewed on 2 Feb 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.