Explore 4 Luxury Hotels in South Side

Name: The Wheeler Mansion
Price range: $724 total

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Best Luxury Hotels in South Side

Hyatt Regency McCormick Place Chicago

2233 S Martin Luther King Dr Chicago IL

Fully refundableReserve now, pay when you stay

$239 nightly

$281 total

Mar 13 - Mar 14

Total with taxes and fees

This hotel's 3 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the 24-hour business center, ...

9.2/10 Wonderful! (1,065 reviews)

Clean toom beautiful views

Reviewed on Mar 3, 2026

Best Western Grant Park Hotel

1100 S Michigan Ave Chicago IL

$79 nightly

$93 total

Mar 5 - Mar 6

Total with taxes and fees

A restaurant and a 24-hour gym are featured at this hotel. WiFi in public areas is free. Valet parking, a computer station, and dry cleaning are also ...

8.2/10 Very Good! (2,690 reviews)

It was in a good location. The staff was very nice however I was breaking out in hives multiple times and I believe it’s due to the sheets. I have very sensitive skin and once something hits my skin I break into hives and I did not happen until I took a nap in the bed so I put a damper into my ...

Reviewed on Mar 4, 2026

Chinatown Hotel Chicago

214 West 22nd Place Chicago IL

$93 nightly

$109 total

Mar 9 - Mar 10

Total with taxes and fees

Free WiFi in public areas, a communal living room, and express check-out are available at this hotel. Luggage storage and a safe deposit box are also ...

5.4/10 (1,000 reviews)

The hotel is safe and FOR THE PRICE it was mostly clean, except under the bed. Fixtures and the hallways show wear and water pressure was a little weak, but shower was hot. If the room rate was typical for Chicago, it would have been disappointing. So that needs to be considered.

Reviewed on Feb 20, 2026

The Wheeler Mansion

2020 South Calumet Avenue Chicago IL

$620 nightly

$724 total

Mar 5 - Mar 6

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free cooked-to-order breakfast, free WiFi, and free self parking. Families will appreciate the arcade/game ...

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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 Luxury Hotels

Do you want to stay at an elegant 5 star hotel for your next getaway? Do you want to be pampered like royalty? When you're ready, the South Side luxury hotels are the plush oasis you’ve been looking for.

Choose from the best luxury hotels in South Side to make your stay as comfortable and memorable as possible. Deluxe amenities await you upon check-in—perks like a heated pool, luxurious spa, and 24-hour reception service will cater to your every need, no matter the hour. If you’re tired from the day’s activities and don’t feel like wandering around to look for a meal, sit down to dinner at one of the high-end restaurants on property or contact room service for a sophisticated dining experience in the comfort of your own suite. Getting to and from the airport will be an easy task as well because most of these fancy hotels offer a free shuttle service for easy transportation.

We want you to enjoy your next vacation in style and the top luxury resorts in South Side will help you do just that. Browse Travelocity right now to find amazing deals on the best luxury hotels and 4 star hotels in South Side, and plan your next opulent escape.

South Side hotels essential information

Accommodation	472 hotels
Lowest Price	$93
Highest Price	$724
Popular hotels	The Wheeler Mansion, Best Western Grant Park Hotel, Hyatt Regency McCormick Place Chicago , Chinatown Hotel Chicago