South Side Romantic Vacations
Book a Romantic Hotel + Flight or Car together to unlock savings
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Better together
Save up to ₩234,741 when you book a flight and hotel together*
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With 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
Fall in love again at this eco-certified hotel. You and your special someone are sure to love the in-room massages, al fresco dining, and premium mattresses. ...
9/10 Wonderful! (1,004 reviews)
Couples like: onsite spa services, al fresco dining
Travelers say...
"Great staff. Would stay here again."
Reviewed on Aug 2, 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! (1 review)
"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 (1,003 reviews)
"No frills hotel room with a reasonable price for Chicago and a great location to walk downtown. Also has parking very near for Chinatown at 18.99 for 24 hrs."
Reviewed on Jul 31, 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.