South Side Romantic Vacations
Book a Romantic Hotel + Flight or Car together to unlock savings
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Save up to NT$5,067 when you book a flight and hotel together*
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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! (1,015 reviews)
Couples like: onsite spa services, al fresco dining
Travelers say...
"Good for family stay. Safe place and walkable to nearby lakeshore."
Reviewed on 2025/8/14
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! (2 reviews)
"A unique place to stay near the convention centre."
Reviewed on 2025/6/23
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 (1,000 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 2025/7/31
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.