Discover a selection of 2,000 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$ 170 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.
Top rated rentals — Chicago

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

Our 2022 holiday accommodation listings offer a large selection of 2,119 holiday rentals around Chicago. From 373 holiday houses to 1,695 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:

  • Lakeview: 374 holiday homes
  • The Loop: 814 holiday homes
  • Near South Side: 926 holiday homes
  • River North: 626 holiday homes
  • West Town: 931 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:

  • Chicago 83rd Street Station (Avalon Park): 2,019 holiday houses
  • Original Playboy Mansion: 2,056 holiday houses
  • Ogilvie Transportation Center: 2,057 holiday houses
  • 333 West Wacker Drive: 2,042 holiday houses
  • Chicago 47th Street Station (Kenwood): 2,036 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 373 Houses in Chicago. Our other popular types of Chicago holiday rentals include:

  • Condos/Apartments: 1,695 self catering accommodations
  • Townhouses: 33 self catering accommodations
  • Studios: 1,426 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 321 holiday homes with pool available in Chicago. Please use our search bar to access the selection of holiday rentals available.

Explore destinations around Chicago

374 holiday rentals
The Loop
814 holiday rentals
Near South Side
926 holiday rentals
River North
626 holiday rentals
West Town
931 holiday rentals
Lake View East
210 holiday rentals
Logan Square
531 holiday rentals
Theatre District
382 holiday rentals
Near North Side
749 holiday rentals
Wicker Park
869 holiday rentals
90 holiday rentals
West Loop
820 holiday rentals
81 holiday rentals
Rush and Division
369 holiday rentals
Grand Boulevard
35 holiday rentals
76 holiday rentals
Humboldt Park
93 holiday rentals
Rogers Park
95 holiday rentals
West Lakeview
89 holiday rentals
101 holiday rentals