South Side Vacations from $392
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The Latest South Side vacation packages
Price found within the past 48 hours. Click for updated prices.
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
3 out of top 10 points of interest in this area
Art and history abound in this architecturally impressive and leafy neighborhood between Washington Park and the shores of Lake Michigan.
Chinatown
If you're spending time in Chinatown, you might enjoy attractions like Chinese American Museum of Chicago and On Leong Building. You might also enjoy the neighborhood's ample dining options before hopping on the metro at Cermak-Chinatown Station to see more of the city.
Bridgeport
Well-liked for its restaurants and churches, Bridgeport is worth a visit. Check out the variety of things to see and do like Zhou B Art Center and Bridgeport Art Center, and jump on the metro at Halsted Station (Orange Line) to get around the city.
Bronzeville
Travelers choose Bronzeville for its abundant dining options. Hop aboard the metro at 35th-Bronzeville-IIT Station or Indiana Station and check out top sights like Lake Michigan.
Woodlawn
2 out of top 10 points of interest in this area
Woodlawn is well-liked for its beaches and restaurants. If you're hoping to get in some sightseeing, Lake Michigan and Obama Presidential Center are top spots, and you can jump on the metro at Cottage Grove Station or King Drive Station to get around.
Stay near popular South Side attractions
University of Chicago
8.6/10 (3,689 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.
Rate Field
8.6/10 (235 reviews)
Catch an event at Rate Field during your trip to Chicago. Experience the entertainment choices and acclaimed theater scene in this vibrant area.
Griffin Museum of Science and Industry
9.2/10 (1,796 reviews)
This large, interactive museum contains a coal mine and World War II submarine among its many attractions.
Illinois Institute of Technology
7.0/10 (4 reviews)
Walk around the campus at Illinois Institute of Technology during your visit to Chicago. Experience the acclaimed art scene and fascinating museums in this vibrant area.
Barack Obama Residence
You can find out about the history of Chicago when you stop by Barack Obama Residence. Stroll along the lakeside in this family-friendly area, or check out its top-notch restaurants.
Rainbow Beach
Why not spend a lazy afternoon at Rainbow Beach during your trip to Chicago? Stroll along the beaches or visit the shops while you're in the area.
Obama Presidential Center
You can spend an afternoon exploring the galleries in Obama Presidential Center during your trip to Chicago. Wander the beaches and gardens while you're in the area.
Wabash Ave YMCA
You can find out about the history of Chicago when you stop by Wabash Ave YMCA. Wander the area's Chinatown or simply enjoy one of its top-notch restaurants.
What to do in South Side
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
$158
per adult
80% of travellers recommend
South Side Hotel Deals
Chicago Lake Shore Hotel
4900 S Lake Shore Dr Chicago IL
$135 nightly
$159 total
Nov 1 - Nov 2
Total with taxes and fees
7/10 Good! (1,005 reviews)
"Definitely a motel vibe, no elevator. Nice staff and clean rooms."
Reviewed on Oct 5, 2026
Holiday Inn Chicago – Midway Airport S by IHG
7353 S Cicero Avenue Chicago IL
Fully refundable
$149 nightly
$173 total
Oct 25 - Oct 26
Total with taxes and fees
8.2/10 Very Good! (1,000 reviews)
"There was no bottled water available in the room or purchase up front. Limited resources. Won’t stay here again"
Reviewed on Oct 7, 2026
Jaslin Hotel
261 West Cermak Rd Chicago IL
$159 nightly
$189 total
Oct 15 - Oct 16
Total with taxes and fees
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.
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
