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! (1,512 reviews)

Couples like: onsite spa services, al fresco dining

Travelers say...

"Bar restaurant was pretty good. Ramen spot was really good. Room was very clean! Left a shirt behind and there is a service to deliver it to me. Very nice touch"

Reviewed on Oct 25, 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 ...

9.6/10 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 Oct 15, 2026

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 (1,011 reviews)

"Firstly, there are no elevators/lifts so anyone who cannot climb flights of stairs may have difficulty. Secondly, the shower in my room was about 1ft above the shower floor and stepping out of it was simply dangerous - anyone with mobility issues would likely fall over. Plus, the lighting in my shower ..."

Reviewed on Oct 26, 2026

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.