South Side Vacations from $313
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The Latest South Side vacation packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was $730, price is now $494 per person
$494
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (5,555 reviews)
The location is in the heart of the city,
Literally everything is walking distance My husband amd loved the hotel.
Reviewed on Oct 31, 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
Art and history abound in this architecturally impressive and leafy neighborhood between Washington Park and the shores of Lake Michigan.
Stay near popular South Side attractions
What to do in South Side
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
Chicago's Navy Pier Centennial Wheel Ticket
$24
per adult
100% of travellers recommend
South Side Hotel Deals
Chicago Lake Shore Hotel
4900 S Lake Shore Dr Chicago IL
$143 nightly
The price is $168 total per night from Nov 2 to Nov 3
$168 total
Nov 2 - Nov 3
Total with taxes and fees
7/10 Good! (1,001 reviews)
"Room was well decorated!"
Reviewed on Oct 30, 2026
Holiday Inn Chicago – Midway Airport S by IHG
7353 S Cicero Avenue Chicago IL
Fully refundable
$128 nightly
The price is $149 total per night from Nov 4 to Nov 5
$149 total
Nov 4 - Nov 5
Total with taxes and fees
Jaslin Hotel
261 West Cermak Rd Chicago IL
Fully refundableReserve now, pay when you stay
$138 nightly
The price is $164 total per night from Nov 24 to Nov 25
$164 total
Nov 24 - Nov 25
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.
