Where to stay around Southwest Side, US?

Our 2018 property listings offer a large selection of 1,895 vacation rentals near Southwest Side. From 951 Hotels to 747 Condos/Apartments, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Southwest Side for a holiday or a weekend are on VRBO.

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

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

  • Indiana: 2,473 vacation rentals
  • Lake Michigan: 13,596 vacation rentals
  • Lakeview: 272 vacation rentals
  • River North: 338 vacation rentals
  • Chicago Loop: 680 vacation rentals

And VRBO offers you the chance to discover many other popular destinations in Southwest 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 Southwest 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 Southwest Side:

  • Evanston: 1,318 rentals
  • Naperville: 213 rentals
  • Oak Park: 1,761 rentals
  • Des Plaines: 256 rentals
  • Skokie: 1,726 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 Southwest 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 Southwest Side are:

  • Chicago Ohare International Airport (ORD): 2,872 vacation rentals
  • Chicago Midway International Airport (MDW): 2,528 vacation rentals
  • Gary Chicago International Airport (GYY): 173 vacation rentals

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

Near which points of interest can I spend my holidays in Southwest Side?

VRBO offers a large selection of rentals near lovely places in Southwest Side. From VRBO travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Wrigley Field: 2,257 rentals
  • Millennium Park: 934 rentals
  • McCormick Place: 1,193 rentals
  • Chicago Water Tower: 1,764 rentals
  • Navy Pier: 1,032 rentals

But there are many other points of interest around Southwest Side listed on VRBO where you can find your place to stay. Just write your wanted destination in our search bar and have a look at our selection.