Photo by Steve Luzzo

Far Southwest Side holiday homes

We found 1,555 holiday rentals — enter your dates for availability

  • 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 Far Southwest Side getaway

Learn about the unique charm of Far Southwest Side with a stay in a holiday home rental. This city has something for everyone. McCormick Place and Soldier Field are just a couple of the must-see attractions in the area. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in and around Far Southwest Side

Are you searching for things to do in the area? Venture out of your holiday home and experience everything that Far Southwest Side has to offer. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Ravisloe Country Club (11 mi / 17.7 km)
  • Galloping Ghost (11.2 mi / 18.1 km)
  • Lincoln Park Zoo (14 mi / 22.6 km)
  • Cog Hill Golf & Country Club (14.4 mi / 23.2 km)
  • Harborside International Golf Center (4.7 mi / 7.6 km)
  • Coyote Run Golf Course (11.9 mi / 19.2 km)

Exploring the natural landscape of Far Southwest Side

Whether you're looking for fun outdoor activities or just want to appreciate the scenery, Far Southwest Side is a great place to get out in nature. Here are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • Grant Park (11 mi / 17.7 km)
  • Millennium Park (11.6 mi / 18.6 km)
  • Abbott Park (3 mi / 4.8 km)
  • Jackson Park (6.5 mi / 10.5 km)
  • Calumet Park (7.8 mi / 12.5 km)
  • Anna and Frederick Douglass Park (9.9 mi / 15.9 km)

Travelling to and around Far Southwest Side

If you prefer to travel by train, Chicago 95th Street Station (Beverly Hills), Chicago 99th Street Station (Beverly Hills) and Chicago 91st Street Station (Beverly Hills) are the main stations in the city. Consider catching a ride on the metro at 95th Street - Longwood Station or 103rd Street Washington Heights Station to more easily navigate the city.

Frequently asked questions

How much does it cost to rent a holiday home in Far Southwest Side?
The average price for a holiday home in Far Southwest Side depends on several factors, such as property type, season and length of stay. Whether you’re in search of a sprawling villa with lots of space or a comfy cabin for you and your other half, just enter your travel dates to discover some great-value stays.
How much does it cost to rent a beach house in Far Southwest Side?
Prices for beach houses in Far Southwest Side may vary depending on the size and type of the property and when you’re travelling. All you have to do is enter your travel dates into Bookabach and how many guests to view holiday home options and prices. From there you can use the filters to refine your search by ratings, nearby activities, amenities and more.
How old do you have to be to rent a holiday home in Far Southwest Side?
We recommend checking with the Far Southwest Side holiday property you’re looking at on Bookabach as the age limit differs. However, typically it’s 16, 18 or 21.
How long can I rent a holiday home in Far Southwest Side for?
It’s really down to the Far Southwest Side property. To view all available options offering extended stays, simply enter your travel dates and number of guests into Bookabach’s search page. Enjoy having the whole place to yourself, along with comforts such as a full kitchen, air conditioning and a yard where the little ones can play. Keep your eyes peeled for long-term stays that offer weekly or monthly discounts.

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