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! (1 review)
"A unique place to stay near the convention centre."
Reviewed on 2025/6/23
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! (2,556 reviews)
"great"
Reviewed on 2025/7/10
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! (1,006 reviews)
Overall enjoyable stay, with event at Soldier Fie
"Good place to stay for a Concert at Soldier Field. By in large not bad, comfortable bed. Bathroom could have used a spot more cleaning,. Parking was not the best. Their parking lot was full, and no Valet parking. Had to park in Convention Center parking garage, with about a 15 min walk back to the ..."
Reviewed on 2025/7/10
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.