Southwest Side holiday rentals

We found 3,165 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts - Southwest Side

Showing deals for:31 Oct - 7 Nov
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Book a holiday rental for your Southwest Side getaway

Learn about the unique charm of Southwest Side with a stay in a holiday home rental. This city has something for everyone. McCormick Place and Michigan Avenue are just a couple of the must-see attractions in the area. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Sightseeing in and around Southwest Side

Are you looking for things to do while you're in town? Venture out of your cosy holiday rental and experience everything that makes Southwest Side a fun spot to go on holiday. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Dave & Buster's (8.3 mi / 13.4 km)
  • Lincoln Park Zoo (9.6 mi / 15.4 km)
  • Cog Hill Golf & Country Club (15.3 mi / 24.7 km)
  • Ravisloe Country Club (16 mi / 25.8 km)
  • Galloping Ghost (8.1 mi / 13 km)
  • Amazing Chicago's Funhouse Maze (8.4 mi / 13.5 km)

Exploring the natural landscape of Southwest Side

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Southwest Side is a great place to spend some time outside. Here are a few of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • Millennium Park (7.5 mi / 12 km)
  • Grant Park (7 mi / 11.3 km)
  • Washington Park (4.7 mi / 7.5 km)
  • Anna and Frederick Douglass Park (4.9 mi / 7.9 km)
  • Garfield Park (6.3 mi / 10.2 km)
  • Jackson Park (6.4 mi / 10.3 km)

How to get to and around Southwest Side

The nearest airport is in Chicago Midway Airport (MDW), located 2 mi (3.3 km) from the city centre.

You can see more of Southwest Side by jumping on the metro at Kedzie Station (Orange Line), Western Station (Orange Line) or Pulaski Station (Orange Line).

Frequently asked questions

How much does it cost to rent a holiday home in Southwest Side?
A number of factors influence how much you'll pay for a holiday home in Southwest Side, like the season, length of stay and type of property. But, all our holiday homes have something in common — unbeatable value. Just enter your travel dates to find your perfect match.
How much does it cost to rent a beach house in Southwest Side?
The average price for a holiday home near the beach in Southwest Side depends on when you're going and the type and size of property you want. You can easily and quickly find prices on Stayz by entering your destination and travel dates. Then use the handy filter tool to choose the number of bedrooms and amenities important to you, such as air conditioning, WiFi and a hot tub.
How old do you have to be to rent a holiday home in Southwest Side?
Age restrictions can vary across properties on Stayz, so double-check the rules of the holiday home in Southwest Side you're considering. But typically, it's 16, 18 or 21.
How long can I rent a holiday home in Southwest Side for?
The amount of time you can rent a Southwest Side holiday home for varies depending on the property. Just tap in your travel dates to find options offering extended stays. They feature all the things you need to make your extended getaway more convenient and enjoyable, like air conditioning and laundries. Some Stayz holiday homes may also offer discounted weekly or monthly prices, so you can stick around for longer for less.

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