Southwest Side holiday homes, IL, USA: holiday houses & more

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Find properties near top attractions in Southwest Side

Wrigley Field

Find the best place to stay - Southwest Side

View from the front entrance landing. The open floor plan is great for families

Walking distance to restaurants, shops and Lake Michigan,

Sleeps 6 · 2 bedrooms · 2 bathrooms

Unit with 1 King size bed. Exact unit will be assigned upon arrival. Views, colors and decor may vary.

Explore Chicago! Free Breakfast, Fully-equipped Kitchen, Pet-friendly Property!

Sleeps 3 · 1 bedroom · 1 bathroom

Peace of mind
Our Book with Confidence guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

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 Navy Pier 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:

Galloping Ghost (8.1 mi / 13 km)
Lincoln Park Zoo (9.6 mi / 15.4 km)
Cog Hill Golf & Country Club (15.3 mi / 24.7 km)
Orland Park Sportsplex (16.6 mi / 26.7 km)
Dave & Buster's (8.3 mi / 13.4 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:

Grant Park (7 mi / 11.3 km)
Millennium Park (7.5 mi / 12 km)
Washington Park (4.7 mi / 7.5 km)
Anna and Frederick Douglass Park (4.9 mi / 7.9 km)
Lakefront Trail (6 mi / 9.6 km)
Garfield Park (6.3 mi / 10.2 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 Bookabach 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 Bookabach, 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 Bookabach holiday homes may also offer discounted weekly or monthly prices, so you can stick around for longer for less.