South Side Vacations from $233
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The Latest South Side vacation packages
Price found within the past 48 hours. Click for updated prices.
Holiday Inn Chicago - Schaumburg by IHG
Save 100% on your flight
Price was $359, price is now $233 per person
$233
per person
Apr 9 - Apr 12
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (999 reviews)
Staff was very courteous however the hotel needs to be updated. One little tiny bar of soap in the room was rather skimpy.
Reviewed on Jan 11, 2026
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $497, price is now $332 per person
$332
per person
Apr 6 - Apr 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
Service was amazing and the location was perfect. Would definitely stay here again.
Reviewed on Jan 28, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,083, price is now $740 per person
$740
per person
Mar 12 - Mar 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The room was boring thought it would be cleaner updated for the price best part was the view
Reviewed on Jan 24, 2026
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
Enjoy the collegiate vibe when you visit University of Chicago, during your travels in Chicago. Stroll along the lakeside or experience the acclaimed art 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.
Illinois Institute of Technology
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.
What to do in South Side
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
88% of travellers recommend
Chicago Bulls Basketball Game at United Center
$61
per adult
80% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
South Side Hotel Deals
SpringHill Suites by Marriott Chicago Chinatown
2357 S WENTWORTH AVE Chicago IL
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $129 total per night from Feb 6 to Feb 7
$129 total
Feb 6 - Feb 7
Total with taxes and fees
9.4/10 Exceptional! (1,015 reviews)
Everything was wonderful!! The staff were all really kind and attentive and the room was spacious and clean. The bed was really comfortable and the blackout curtains made it extra easy to sleep in. We definitely know where we'll be staying next time we're in town!!
Reviewed on Jan 27, 2026
Jaslin Hotel
261 West Cermak Rd Chicago IL
Fully refundableReserve now, pay when you stay
$100 nightly
The price is $118 total per night from Feb 11 to Feb 12
$118 total
Feb 11 - Feb 12
Total with taxes and fees
8.8/10 Excellent! (1,177 reviews)
Great service and clean roomd
Reviewed on Jan 23, 2026
Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
6500 S Cicero Ave Chicago IL
Fully refundable
$108 nightly
The price is $127 total per night from Feb 8 to Feb 9
$127 total
Feb 8 - Feb 9
Total with taxes and fees
8.8/10 Excellent! (1,291 reviews)
We had a 1 minute check in process! Room was huge and clean!
Reviewed on Jan 26, 2026
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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- 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
- Hyde Park Hair Salon
- Robie House
- Visit Grand Boulevard
- University of Chicago
- Visit Kenwood
- Midway Plaisance
- Visit Hyde Park
- Rockefeller Memorial Chapel
- Car rentals near Chicago
- Car rentals near 4944 S Woodlawn Ave
- Car rentals near Hyde Park
- Enterprise Rental Cars in Hyde Park
- Hertz Rental Cars in Hyde Park
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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.
