South Side Romantic Holidays
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Top Romantic South Side Hotels
Hyatt Regency McCormick Place Chicago
2233 S Martin Luther King Dr, Chicago, IL
Stay at this 4-star eco-certified hotel in Chicago. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,003 reviews)
"The hotel was great and the saff (especially Tony) were amazing."
Reviewed on 6 Aug. 2025
The Wheeler Mansion
2020 South Calumet Avenue, Chicago, IL
Stay at this 4-star luxury hotel in Chicago. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Soldier Field and Grant Park are located ...
10/10 Exceptional! (1 review)
"A unique place to stay near the convention centre."
Reviewed on 23 Jun. 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 (1,000 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 31 Jul. 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.