South Side Romantic Vacations
Book a Romantic Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥45,448 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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4 Night Romantic vacations in South Side
Price found within the past 48 hours. Click for updated prices.
Top Romantic South Side Hotels
Hyatt Regency McCormick Place Chicago
2233 S Martin Luther King Dr Chicago IL
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! (1,065 reviews)
Couples like: onsite spa services, al fresco dining
Travelers say...
Very nice Hotel. Nice room and view!! The staff were friendly. We will be back to stay at this Hotel.
Reviewed on Jan 31, 2026
The Wheeler Mansion
2020 South Calumet Avenue Chicago IL
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 Jun 23, 2025
Chinatown Hotel Chicago
214 West 22nd Place Chicago IL
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 (1,002 reviews)
Great rooms With upgraded, Recently Renovated!
Reviewed on Feb 2, 2026
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.
