Discover a selection of 1,000 vacation rentals in South Side, US that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and kitchens. Prices start at $150 per night, and houses and condos are popular options for a stay in South Side. Either way, you'll find a rental for everyone's needs.
AsyncDestinationUrgency
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy

How many vacation rentals are available around South Side, US?

Our 2020 property listings offer a large selection of 770 vacation rentals around South Side. From 140 house rentals to 566 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

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:

  • Torch Lake: 6,830 vacation rentals
  • Near North Side: 253 vacation rentals
  • Chicago Loop: 249 vacation rentals
  • Lake View: 204 vacation rentals
  • Lincoln Park: 355 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: 605 rentals
  • Merrillville: 154 rentals
  • Forest Park: 875 rentals
  • Oak Park: 857 rentals
  • Tinley Park: 28 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): 1,214 vacation rentals
  • O'Hare International Airport (ORD): 1,267 vacation rentals
  • Gary Chicago International Airport (GYY): 266 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 South Side?

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

  • Indiana Dunes National Lakeshore: 491 rentals
  • Wrigley Field: 1,131 rentals
  • Grant Park: 702 rentals
  • Chicago Water Tower: 1,114 rentals
  • McCormick Place: 759 rentals

But there are many other points of interest around South 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.

Explore destinations around South Side

Evanston
605 vacation rentals
Merrillville
154 vacation rentals
Forest Park
875 vacation rentals
Oak Park
857 vacation rentals
Tinley Park
28 vacation rentals
Hammond
139 vacation rentals
Northbrook
161 vacation rentals
Des Plaines
338 vacation rentals
Schererville
105 vacation rentals
Oak Brook
237 vacation rentals
Wheeling
167 vacation rentals
Downers Grove Township
268 vacation rentals
Lansing
84 vacation rentals
Elmhurst
284 vacation rentals
Glenview
339 vacation rentals
Elmwood Park
836 vacation rentals
Skokie
655 vacation rentals
Mount Prospect
182 vacation rentals
Orland Park
72 vacation rentals
Wilmette
340 vacation rentals