Discover a selection of 1,500 holiday homes in Chicago, IL, US that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Bookabach holiday homes have the best amenities for hanging out with the people that matter most, including pool and internet/WiFi. Prices start at NZ$ 255 per night, and holiday houses and apartments are popular options for a stay in Chicago. Either way, you'll find accommodation for everyone's needs.

How many holiday homes are available around Chicago, IL, US?

Our 2021 holiday accommodation listings offer a large selection of 1,468 holiday rentals around Chicago. From 248 holiday houses to 1,122 apartments, find unique holiday house for you to enjoy a memorable holiday or a weekend with your family and friends. The best place to stay around Chicago is on Bookabach.

What is the best area to stay when travelling to Chicago?

Whether you are travelling solo or with family and friends, here are the areas with the largest selection of holiday accommodations for a long holiday or just a weekend break in Chicago:

  • West Town: 599 holiday homes
  • The Loop: 706 holiday homes
  • Near West Side: 477 holiday homes
  • Lakeview: 204 holiday homes
  • Lincoln Park: 547 holiday homes

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

What are the most popular points of interest and landmarks to stay near when travelling to Chicago? offers a large selection of holiday accommodations near great places in Chicago. From travellers, the most popular points of interest to stay near are:

  • Elijah Muhammad House: 1,410 holiday houses
  • Garfield Park: 1,459 holiday houses
  • Chicago 99th Street Station (Beverly Hills): 1,385 holiday houses
  • Court Theatre: 1,411 holiday houses
  • John G. Shedd Aquarium: 1,402 holiday houses

But there are many other points of interest around Chicago listed on where you can find your place to stay. Please use our search bar to access the selection of holiday rentals available near the point of interest of your choice.

Can I rent Houses in Chicago?

Yes, of course. offers 248 Houses in Chicago. Our other popular types of Chicago holiday rentals include:

  • Condos/Apartments: 1,122 self catering accommodations
  • Townhouses: 22 self catering accommodations
  • Studios: 1,010 self catering accommodations

But you can also enjoy a great stay in one of our other holiday homes including Cabins and more.

Can I find a holiday accommodation with pool in Chicago?

Yes, you can select your preferred holiday accommodation with pool among our 190 holiday homes with pool available in Chicago. Please use our search bar to access the selection of holiday rentals available.

    Explore destinations around Chicago

    West Town
    599 holiday rentals
    The Loop
    706 holiday rentals
    Near West Side
    477 holiday rentals
    204 holiday rentals
    Lincoln Park
    547 holiday rentals
    Near South Side
    770 holiday rentals
    Near East Side
    390 holiday rentals
    Near North Side
    642 holiday rentals
    44 holiday rentals
    Ukrainian Village
    241 holiday rentals
    Irving Park
    35 holiday rentals
    Lower West Side
    33 holiday rentals
    Lincoln Square
    318 holiday rentals
    Logan Square
    316 holiday rentals
    1,004 holiday rentals
    North Center
    107 holiday rentals
    West Loop
    635 holiday rentals
    Rogers Park
    54 holiday rentals
    Grand Boulevard
    32 holiday rentals
    51 holiday rentals