Where to stay near Chicago?

Our 2021 accommodation listings offer a large selection of 1,444 holiday rentals near Chicago. From 243 Houses to 1,103 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:

  • The Loop: 690 holiday homes
  • West Loop: 631 holiday homes
  • Logan Square: 306 holiday homes
  • Near South Side: 745 holiday homes
  • Printers Row: 295 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:

  • 311 S Wacker Dr: 1,383 holiday rentals
  • Wrigley Building: 1,404 holiday rentals
  • Chicago McCormick Place Station: 1,405 holiday rentals
  • Chicago 103rd Street Station (Rosemoor): 1,316 holiday rentals
  • Chicago 79th Street Station (Cheltenham): 1,407 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 243 Houses in Chicago. Our other popular types of Chicago holiday rentals include:

  • Condos/Apartments: 1,103 holiday houses
  • Townhouses: 22 holiday houses
  • Studios: 983 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 177 holiday homes with pool available in Chicago. Please use our search bar to access the selection of holiday rentals available.

    Explore destinations around Chicago

    The Loop
    690 holiday rentals
    West Loop
    631 holiday rentals
    Logan Square
    306 holiday rentals
    Near South Side
    745 holiday rentals
    Printers Row
    295 holiday rentals
    Near North Side
    627 holiday rentals
    Near West Side
    478 holiday rentals
    West Town
    587 holiday rentals
    North Center
    104 holiday rentals
    Sheffield Neighbors
    59 holiday rentals
    Rush and Division
    248 holiday rentals
    54 holiday rentals
    Lincoln Park
    529 holiday rentals
    River North
    499 holiday rentals
    198 holiday rentals
    979 holiday rentals
    West Bucktown
    58 holiday rentals
    Lake View East
    90 holiday rentals
    West Ridge
    18 holiday rentals
    Lower West Side
    34 holiday rentals