
Deals on vacations and trips to South Side
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South Side flight + hotel vacation packages
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Illinois Beach Hotel
Save 100% on your flight
per person
Aug 13 - Aug 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area is provided and the front desk is staffed around-the-clock.

Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
per person
Aug 23 - Aug 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A restaurant is on site and multilingual staff is available around-the-clock at the 24-hour front desk. Unwind with a drink at one of the 2 bars/lounges and enjoy free perks like buffet breakfast and WiFi in public areas. There's a 24-hour gym on site, and a coffee shop and a snack bar/deli are also provided.

La Banque Hotel
Save 100% on your flight
per person
Jul 20 - Jul 23
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the 24-hour business center. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and concierge services.

Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
per person
Sep 5 - Sep 7
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare. Enjoy the gym and perks like free WiFi.

Harrah's Joliet Casino & Hotel
Save 100% on your flight
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (CHI)
This hotel features 3 restaurants, a bar/lounge, and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A coffee shop, express check-out, and luggage storage are also on offer.
Top South Side hotels deals

Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
6500 S Cicero Ave, Chicago, IL
Free Cancellation
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and a free airport shuttle. Traveling for business? Take advantage of the 24-hour business center, laundry service, and conference space. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and laundry facilities.
Breakfast included
Free airport shuttle

Jaslin Hotel
261 West Cermak Rd, Chicago, IL
Free Cancellation
A 24-hour gym is featured at this hotel, along with luggage storage and a safe deposit box. Multilingual staff at the 24-hour front desk can provide around-the-clock assistance.
Air conditioning
Gym

SpringHill Suites by Marriott Chicago Chinatown
2357 S WENTWORTH AVE, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
This hotel doesn't skimp on freebies - guests receive free buffet breakfast and free WiFi. Business travelers can take advantage of the 24-hour business center. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and laundry facilities.
Breakfast included
Free WiFi

Hyatt Place Chicago-South/University Medical Center
5225 S Harper Ave, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A free area shuttle is offered as well.

Carlton Inn Midway
4944 S Archer Ave, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
This motel doesn't skimp on freebies - guests receive free continental breakfast, free self parking, and a free airport shuttle. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.
Breakfast included
Free airport shuttle
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.
Popular places to visit

University of Chicago
4.5/5(1,167 reviews)
Take a campus tour or just explore the area around University of Chicago, a top university in Chicago. Stroll along the lakeside or experience the fascinating museums in this vibrant area.

Chicago Museum of Science and Industry
4.5/5(1,381 reviews)
This large, interactive museum contains a coal mine and World War II submarine among its many attractions.

Illinois Institute of Technology
3.5/5(4 reviews)
Walk around the campus at Illinois Institute of Technology during your visit to Chicago. Experience the acclaimed theater scene and fascinating museums in this vibrant area.
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