
South Side Vacations from $449
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The Latest South Side vacation packages

Wind Creek Southland Casino and Hotel
Reviewed on May 1, 2026

Hotel Riu Plaza Chicago
Reviewed on May 1, 2026

Level Chicago Fulton Market
Reviewed on Apr 25, 2026

Hotel Felix River North/Magnificent Mile
Reviewed on Apr 27, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
Reviewed on Apr 29, 2026
Where to stay in South Side

Hyde Park
Art and history abound in this architecturally impressive and leafy neighborhood between Washington Park and the shores of Lake Michigan.
Discover the most popular places to visit in South Side

University of Chicago
Enjoy the collegiate vibe when you visit University of Chicago, during your travels in Chicago. Stroll along the lakeside or experience the acclaimed theater scene in this vibrant area.

Griffin Museum of Science and Industry
This large, interactive museum contains a coal mine and World War II submarine among its many attractions.

Jackson Park
Jackson Park is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Amble around this vibrant area's lakeside or experience its fascinating museums.
What to do in South Side

Skydeck - Willis Tower Admission
South Side Hotel Deals

Chicago Lake Shore Hotel
it's good for this price, close to the university with clean rooms, a little bit noisy, overral acceptable with such low price
Reviewed on Apr 28, 2026

Jaslin Hotel
The room was spacious and clean.The hotel was close to many shops and restairants, but still quiet. There was a fire station across the street that deployed fire trucks and ambulances very frequently, but it didn't actually disturb us during the night, just be aware if you're sensitive to something ...
Reviewed on Apr 30, 2026

Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
Parking was horrible they don’t tell until the last minute at check in that’s it’s $30 a night for parking. And with the being said you could not park by the hotel you had to walk 2 blocks to get a parking spot horrible just horrible $30 to walk 2 blocks
Reviewed on May 1, 2026
Find the Best South Side Vacation Packages
South Side Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | O'Hare Intl. Airport (ORD) |
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