Photo by by Midway Intl Airport
South Side Vacation Rentals
- Change your mindBook hotels with free cancellation
- Be pickySearch almost a million properties worldwide
Check prices for these dates
In two weeks
In two months
In three months
In four months
Vacation Rentals in South Side

Aparthotel in Bridgeport
The price is ¥37,760
¥60,393 total
includes taxes & fees
Dec 7 - Dec 8

Aparthotel in Downtown Chicago
9.2 out of 10, Wonderful, (987)
The price is ¥15,673
¥22,963 total
includes taxes & fees
Dec 16 - Dec 17

Aparthotel in Downtown Chicago
9.0 out of 10, Wonderful, (384)

Aparthotel in Downtown Chicago
9.4 out of 10, Exceptional, (179)

Aparthotel in Lakeview
9.6 out of 10, Exceptional, (25)
The price is ¥18,232
¥21,402 total
includes taxes & fees
Nov 24 - Nov 25

Cottage in Miller Beach
The price is ¥23,124
¥64,531 total
includes taxes & fees
Dec 2 - Dec 3

Aparthotel in Downtown Chicago
10.0 out of 10, Exceptional, (1)
The price is ¥45,493
¥53,405 total
includes taxes & fees
Nov 25 - Nov 26

Aparthotel in West Town
9.0 out of 10, Wonderful, (17)
The price is ¥10,099
¥22,111 total
includes taxes & fees
Nov 30 - Dec 1
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 vacation rentals that suit your style
Aparthotels
Apartments
Save an average of 15% on thousands of hotels when you're signed in
Top South Side Hotel Reviews

Motel 6 - Chicago, IL
10/10 Excellent
Find out more about South Side
Search for holiday rentals in South Side on Expedia! You can easily find your home rentals, villas, holiday apartments in South Side using one of the methods below:
- View our selection of featured holiday rentals in South Side
- Use the map to find apartments and other holiday homes in the South Side neighbourhood you prefer
- Enter your travel dates to view the best deals on holiday rentals in South Side while they last
Look no further and take a look at our great range of rental properties in South Side!













































































