South Side Luxury Vacations
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Top Luxury South Side Hotels
The Wheeler Mansion
2020 South Calumet Avenue, Chicago, IL
Choose luxury at The Wheeler Mansion, where you can enjoy amenities like pillowtop beds, designer toiletries, and more. The lounge bar, terrace, and garden are ...
10/10 Exceptional! (2 reviews)
"A unique place to stay near the convention centre."
Reviewed on Jun 23, 2025
Best Western Grant Park Hotel
1100 S Michigan Ave, Chicago, IL
Spoil yourself with a luxury vacation in Chicago. Popular amenities include a restaurant and a 24-hour fitness center.
8/10 Very Good! (2,655 reviews)
"clean room"
Reviewed on Sep 24, 2025
Hyatt Regency McCormick Place Chicago
2233 S Martin Luther King Dr, Chicago, IL
Choose luxury at Hyatt Regency McCormick Place Chicago , where you can enjoy amenities like massage services, pillowtop beds, and more. The 2 bars, indoor pool, ...
9/10 Wonderful! (1,031 reviews)
Loved it!
"Enjoyed my stay!!"
Reviewed on Sep 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.
