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! (1,508 reviews)

Couples like: onsite spa services, al fresco dining

Travelers say...

"Great stay would definitely recommend"

Reviewed on 2026/10/23

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 ...

9.6/10 Exceptional! (9 reviews)

"This place is so much better than a regular corporate hotel. It is literally a restored mansion. Breakfast was great. Bed was very comfortable. The outdoor seating and garden in October were so nice to chill in after attending meetings at the convention center (easy 5 minute walk). If available will ..."

Reviewed on 2026/10/15

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 (1,009 reviews)

"Todo bien, mi 4a vez"

Reviewed on 2026/10/23

See all 513 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.