Where to stay around South Side, US?

Our 2019 property listings offer a large selection of 1,697 vacation rentals near South Side. From 796 Condos/Apartments to 722 Hotels, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near South Side for a holiday or a weekend are on VRBO.

What are the most popular destinations to visit in South Side?

There are many lovely places to stay for a holiday trip or just for a weekend in South Side. From VRBO travelers, the top most popular destinations to visit are:

  • Indiana: 2,527 vacation rentals
  • Lake Michigan: 13,604 vacation rentals
  • Lakeview: 301 vacation rentals
  • River North: 344 vacation rentals
  • Chicago Loop: 704 vacation rentals

And VRBO offers you the chance to discover many other popular destinations in South Side! Please use our search bar to access the selection of vacation rentals available in other popular destinations.

What are the main cities to discover in South Side?

Whether you're traveling with family or friends, here are the cities with the largest selection of vacation rentals for a holiday trip or just for a weekend in South Side:

  • Evanston: 1,405 rentals
  • Oak Park: 1,793 rentals
  • Skokie: 1,811 rentals
  • Des Plaines: 275 rentals
  • Wilmette: 438 rentals

For other cities, please use our search bar to access the selection of vacation rentals available.

Can I find easy-access vacation rentals when traveling by plane to South Side?

Yes of course. Our owners offer a large selection of vacation rentals near airports. The airports with a large selection of vacation rentals in South Side are:

  • Chicago Midway International Airport (MDW): 2,576 vacation rentals
  • Gary Chicago International Airport (GYY): 184 vacation rentals
  • Lansing Municipal Airport (IGQ): 144 vacation rentals

For other airports, please use our search bar to access the selection of vacation rentals available.