Discover a selection of 2,500 holiday home rentals in Chicago, IL, US that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Stayz holiday homes have the best amenities for hanging out with the people that matter most, including pool and internet/WiFi. Prices start at AU$ 194 per night, and holiday houses and flats & apartments are popular options for a stay in Chicago. Either way, you'll find holiday accommodation for everyone's needs.
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Top rated rentals — Chicago
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How many holiday accommodation are available around Chicago?

Our 2022 accommodation listings offer a large selection of 2,327 holiday rentals around Chicago. From 404 holiday houses to 1,839 flats & apartments, find unique holiday homes for you to enjoy a memorable holiday or a weekend with your family and friends. The best place to stay around Chicago is on Stayz.

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 rentals for a long holiday or just a weekend break in Chicago:

  • Gold Coast: 362 holiday homes
  • River North: 627 holiday homes
  • Streeterville: 423 holiday homes
  • Rush and Division: 370 holiday homes
  • Old Town Triangle: 87 holiday homes

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

What are the most popular points of interest and landmarks to stay near when travelling to Chicago?

Stayz offers a large selection of holiday homes near great places in Chicago. From Stayz travellers, the most popular points of interest to stay near are:

  • Chicago 103rd Street Station (Rosemoor): 1,972 holiday rentals
  • Ronald McDonald House near Lurie Children’s: 2,084 holiday rentals
  • Chicago McCormick Place Station: 2,077 holiday rentals
  • John Hancock Center: 2,083 holiday rentals
  • 311 S Wacker Dr: 2,083 holiday rentals

But there are many other points of interest around Chicago listed on Stayz 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. Stayz offers 404 Houses in Chicago. Our other popular types of Chicago holiday rentals include:

  • Condos/Apartments: 1,839 holiday houses
  • Townhouses: 35 holiday houses
  • Studios: 1,555 holiday houses

But you can also enjoy a great stay in one of our other holiday rentals 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 363 holiday homes with pool available in Chicago. Please use our search bar to access the selection of holiday rentals available.

Explore destinations around Chicago

Gold Coast
362 holiday rentals
River North
627 holiday rentals
Streeterville
423 holiday rentals
Rush and Division
370 holiday rentals
Old Town Triangle
87 holiday rentals
The Loop
817 holiday rentals
Lakeview
386 holiday rentals
Near South Side
932 holiday rentals
Old Town Chicago
345 holiday rentals
Theatre District
384 holiday rentals
Near North Side
750 holiday rentals
Lake View East
213 holiday rentals
Uptown
1,457 holiday rentals
West Town
938 holiday rentals
Grand Boulevard
35 holiday rentals
Wrigleyville
402 holiday rentals
Rogers Park
98 holiday rentals
West Loop
825 holiday rentals
Wicker Park
881 holiday rentals
Roscoe Village
252 holiday rentals