South Side Romantic Vacations
Book a Romantic Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ₩1,660,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
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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.
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 ...
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
