Photo by Richard Remington

South Side Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Our top choices for South Side holiday rentals

Private kitchen
Stylish Apartment near Chicago Downtown

Aparthotel in Bridgeport

2.0 star property
The price is S$287
includes taxes & fees
10 Jan - 11 Jan, 2026
Stylish Apartment near Chicago Downtown
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top South Side Hotel Reviews

Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG

Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG

10/10 Excellent
"The staff were helpful in explaining the free shuttle to Midway airport.The shuttle picks you up at a point outside the third level. There is a sign indicating the correct spot. You have to tell the staff when you want to get taken back to Midway and they tell you what time to come to the lobby "
Joseph 1-night trip
Posted 1 day ago
Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG