South Side Romantic Vacations
Book a Romantic Hotel + Flight or Car together to unlock savings
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- Plan, book, travel with confidence
Better together
Save up to ￥45,448 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
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! (1,025 reviews)
Couples like: onsite spa services, al fresco dining
Travelers say...
Will be back!
Reviewed on Oct 24, 2025
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 ...
10/10 Exceptional! (3 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. Our guests praise the property condition in our reviews. Popular ...
5.4/10 (1,001 reviews)
Chinatown was a very beautiful area.
Reviewed on Oct 21, 2025
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.
