South Side Vacation Packages
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Top South Side vacation package deals
Price found within the past 48 hours. Click for updated prices.
4.5-star property
The Talbott, Autograph Collection
Downtown Chicago
9.4/10 Exceptional! (165 reviews)
Dec 10 - Dec 14
4 night stay
Austin (AUS) to Chicago (ORD)
Frontier Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $820, price is now $547 per person
$547
per person
found 1 day ago
4.5-star property
Swissotel - Chicago
Downtown Chicago
9/10 Wonderful! (3,512 reviews)
Dec 10 - Dec 14
4 night stay
Austin (AUS) to Chicago (ORD)
Frontier Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $813, price is now $543 per person
$543
per person
found 1 day ago
Good location, close to everything
Reviewed on Sep 21, 2026
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
9.6/10 Exceptional! (1,995 reviews)
Dec 10 - Dec 14
4 night stay
Austin (AUS) to Chicago (ORD)
Frontier Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,743, price is now $1,174 per person
$1,174
per person
found 1 day ago
Can’t wait to come back.
Reviewed on Sep 21, 2026
Top rated hotels for your South Side vacation package
Holiday Inn Chicago – Midway Airport S by IHG
7353 S Cicero Avenue Chicago IL
Free Cancellation
7.54 mi from city center
$162 nightly
The price is $188 total per night
$188 total
Sep 27 - Sep 28
Total with taxes and fees
At Holiday Inn Chicago – Midway Airport S by IHG, guests have access to a 24-hour gym, free WiFi in public areas, and meeting rooms. If you drive, self parking is USD 23 per day, or you can take advantage of the free airport shuttle during limited hours. The 24-hour front desk has multilingual staff ready to help with luggage storage, and answer any questions about the area. Additional amenities include conference space, a 24-hour business center, and express check-out.
Free airport shuttle
Free WiFi
Chicago Lake Shore Hotel
4900 S Lake Shore Dr Chicago IL
1.19 mi from city center
$169 nightly
The price is $199 total per night
$199 total
Sep 23 - Sep 24
Total with taxes and fees
Guests of Chicago Lake Shore Hotel have access to free WiFi in public areas. Free parking is available if you drive. The 24-hour front desk has multilingual staff ready to help with luggage storage, and answer any questions about the area.
Pet friendly
Parking included
Jaslin Hotel
261 West Cermak Rd Chicago IL
Free Cancellation
Reserve now, pay when you stay
3.51 mi from city center
$178 nightly
The price is $211 total per night
$211 total
Sep 29 - Sep 30
Total with taxes and fees
A 24-hour gym and free WiFi in public areas are features at Jaslin Hotel. The 24-hour front desk has multilingual staff ready to help with luggage storage, and answer any questions about the area.
Free WiFi
Air conditioning
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.
Things to do
Chicago CityPASS®: Experience 5 must-see attractions
$144
per adult
94% of travellers recommend
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