Where to stay near Chicago?

Our 2020 accommodation listings offer a large selection of 1,514 holiday rentals near Chicago. From 248 Houses to 1,180 Condos/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 near Chicago is on HomeAway.

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:

  • Chicago Loop: 249 holiday homes
  • West Loop: 269 holiday homes
  • Logan Square: 256 holiday homes
  • Printer's Row: 68 holiday homes
  • Near North Side: 251 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? offers a large selection of holiday homes near great places in Chicago. From travellers, the most popular points of interest to stay near are:

  • Swedish Covenant Hospital: 1,169 holiday rentals
  • Chicago McCormick Place Station: 1,132 holiday rentals
  • Chicago 103rd Street Station (Rosemoor): 1,030 holiday rentals
  • Chicago 79th Street Station (Cheltenham): 1,080 holiday rentals
  • Chicago's Mercury Theater: 1,155 holiday rentals

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: 1,180 holiday houses
  • Studios: 1,018 holiday houses
  • Townhouses: 23 holiday houses

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

Can I find a holiday accommodation with pool in Chicago?

Yes, you can select your preferred holiday accommodation with pool among our 258 holiday homes with pool available in Chicago. Please use our search bar to access the selection of holiday rentals available.

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