South Side Vacations from $645
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The Latest South Side vacation packages
Price found within the past 48 hours. Click for updated prices.
The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was $1,308, price is now $739 per person
$739
per person
Nov 21 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,195 reviews)
The rooms were not very well decorated. The furniture used in the room looks like furniture from a detention house. Not my favorite.
Reviewed on Sep 8, 2025
Arlo Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,268, price is now $822 per person
$822
per person
Nov 21 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,844 reviews)
Very helpful service for those coming out of town and have a car. The staff was very helpful in getting me to the parking garage and from the loading area.
Reviewed on Sep 15, 2025
Where to stay in South Side
Find the best South Side areas and neighborhoods for the activities you enjoy most. Learn more about South Side
Hyde Park
4 out of top 10 points of interest in this area
4.5/5(136 area reviews)
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
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 acclaimed art scene in this vibrant area.
Chicago Museum of Science and Industry
This large, interactive museum contains a coal mine and World War II submarine among its many attractions.
Illinois Institute of Technology
Walk around the campus at Illinois Institute of Technology during your visit to Chicago. Experience the fascinating museums and acclaimed art scene in this vibrant area.
What to do in South Side
Big Bus Chicago Essential Ticket + 360 Chicago
$84
per adult
Chicago's Ultimate City Bike Tour
$60
per adult
100% of travellers recommend
Big Bus Chicago Essential & Shoreline Architecture Cruise
$99
per adult
South Side Hotel Deals
SpringHill Suites by Marriott Chicago Chinatown
2357 S WENTWORTH AVE, Chicago, IL
Fully refundableReserve now, pay when you stay
$179 nightly
The price is $210 total per night from Sep 22 to Sep 23
$210 total
Sep 22 - Sep 23
Total with taxes and fees
9.4/10 Exceptional! (999 reviews)
"We were seeing a show at soldier field, we took the free bus from Reggie's right down the street and saved the $60 parking and dealing with the traffic. The staff are very knowledgeable about the area as well."
Reviewed on Sep 8, 2025
Motel 6 - Chicago, IL
10022 South Halsted Street, Chicago, IL
Fully refundableReserve now, pay when you stay
$75 nightly
The price is $88 total per night from Sep 16 to Sep 17
$88 total
Sep 16 - Sep 17
Total with taxes and fees
6.4/10 (94 reviews)
"It was nice"
Reviewed on Aug 23, 2025
Jaslin Hotel
261 West Cermak Rd, Chicago, IL
Fully refundable
$129 nightly
The price is $152 total per night from Sep 22 to Sep 23
$152 total
Sep 22 - Sep 23
Total with taxes and fees
8.8/10 Excellent! (1,140 reviews)
"Really liked the hotel, location is on the edge of Chinatown. The only negative is misleading info on parking, The pay lot is reasonable, but 2 blocks away, not the most convenient."
Reviewed on Sep 7, 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.
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- Chicago Vacations
- Obama's House
- KAM Synagogue
- 4944 S Woodlawn Ave
- Chicago Museum of Science and Industry
- Elijah Muhammad House
- Visit Washington Park Court
- Smart Museum of Art
- Muddy Waters’ House
- DuSable Museum of African-American History
- Hyde Park Vacations
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- Robie House
- Visit Grand Boulevard
- University of Chicago
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- Midway Plaisance
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- Rockefeller Memorial Chapel
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
