Romantic Hotels in South Side, IL
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Featured South Side Romantic Getaways & Hotels

Hyatt Regency McCormick Place Chicago
2233 S Martin Luther King Dr Chicago IL
Free Cancellation
Reserve now, pay when you stay
$199 nightly
The price is $234 total per night
$234 total
Dec 29 - Dec 30
Total with taxes and fees
At Hyatt Regency McCormick Place Chicago , guests have access to a gym, a sauna, and free WiFi in public areas. Parking is available for USD 40 per night (USD 60 per day for valet parking), and there's also a free casino shuttle. Multilingual staff at the 24-hour front desk can assist with concierge services, dry cleaning/laundry, and luggage storage. Additional amenities include meeting rooms, a conference center, and a 24-hour business center.
Free WiFi
Restaurant

The Wheeler Mansion
2020 South Calumet Avenue Chicago IL
$616 nightly
The price is $724 total per night
$724 total
Jan 13 - Jan 14, 2026
Total with taxes and fees
Guests of The Wheeler Mansion enjoy access to free WiFi in public areas, meeting rooms, and conference space. You can put free parking to good use if you drive. Front-desk staff can assist with tours or tickets, luggage storage, and securing valuables. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls, an off-leash area, and pet-sitting services. Other amenities at this luxury hotel include coffee/tea in a common area, an arcade/game room, and a library.
Breakfast included
All inclusive

Chinatown Hotel Chicago
214 West 22nd Place Chicago IL
Free Cancellation
Reserve now, pay when you stay
$65 nightly
The price is $76 total per night
$76 total
Dec 25 - Dec 26
Total with taxes and fees
Chinatown Hotel Chicago features free WiFi in public areas, microwave in a common area, and refrigerator in a common area. The front desk is staffed 24/7 to help with tours or tickets, securing valuables, and luggage storage. Additional amenities include express check-out, free newspapers, and a water dispenser.
Free WiFi
Air conditioning
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.
South Side hotels essential information
Accommodation | 472 hotels |
|---|---|
Lowest Price | $76 |
Highest Price | $724 |
Popular hotels | Hyatt Regency McCormick Place Chicago , The Wheeler Mansion, Chinatown Hotel Chicago |
Recent Romantic Getaways & Hotels Reviews

SpringHill Suites by Marriott Chicago Chinatown
5/5 Excellent
"Everything was wonderful! From the welcoming feeling when we walked in the door with the bright ambiance and the pleasant smell. They have nice & helpful front desk staff, along with convenient parking . Rooms were spacious, clean and the bed was so comfortable. We were sad to have missed out on the breakfast because we slept in but we had heard it was very good."
A verified traveler stayed at SpringHill Suites by Marriott Chicago Chinatown
Posted 4 days ago
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