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Can I find a vacation rental around Chicago?

Yes, our 2020 property listings offer a large selection of 1,223 vacation rentals near Chicago. From 756 Condos/Apartments to 239 Houses, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Chicago for a holiday or a weekend are on HomeAway.

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

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Chicago:

  • Near North Side: 253 vacation rentals
  • Chicago Loop: 249 vacation rentals
  • Lake View: 204 vacation rentals
  • Lincoln Park: 355 vacation rentals
  • Logan Square: 257 vacation rentals

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

What are the popular points of interest near where I can stay when traveling to Chicago?

HomeAway.com offers a large selection of vacation rentals near lovely places in Chicago. From HomeAway.com travelers, the most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Wrigley Field: 1,131 vacation rentals
  • Grant Park: 702 vacation rentals
  • Chicago Water Tower: 1,114 vacation rentals
  • McCormick Place: 759 vacation rentals
  • Navy Pier: 646 vacation rentals

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

Can I rent Condos/Apartments in Chicago?

Yes, of course. HomeAway.com has 756 Condos/Apartments in Chicago. Our other popular types of vacation rentals in Chicago include:

  • Houses: 239 rentals available
  • Studios: 734 rentals available
  • Townhouses: 31 rentals available

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

Can I find a vacation rental with pool in Chicago?

Yes, you can select your preferred vacation rental with pool among our 179 vacation rentals with pool available in Chicago. Please use our search bar to access the selection of vacation rentals available.

    Explore destinations around Chicago

    Naperville
    365 vacation rentals
    Oakbrook Terrace
    230 vacation rentals
    Evanston
    605 vacation rentals
    Merrillville
    154 vacation rentals
    Aurora
    92 vacation rentals
    Libertyville
    91 vacation rentals
    Joliet
    17 vacation rentals
    Bolingbrook
    174 vacation rentals
    Forest Park
    893 vacation rentals
    Oak Park
    857 vacation rentals
    Downers Grove
    194 vacation rentals
    Tinley Park
    28 vacation rentals
    Wheaton
    206 vacation rentals
    Crystal Lake
    44 vacation rentals
    Hammond
    139 vacation rentals
    Northbrook
    161 vacation rentals
    Warrenville
    163 vacation rentals
    Des Plaines
    338 vacation rentals
    Lombard
    233 vacation rentals
    Bloomingdale
    220 vacation rentals