Where to stay around Chicago, IL?

Our 2018 property listings offer a large selection of 1,025 vacation rentals near Chicago. From 763 Condos/Apartments to 585 Studios, 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 VRBO.

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:

  • Chicago Loop: 159 vacation rentals
  • Old Town: 134 vacation rentals
  • Lakeview: 211 vacation rentals
  • Wicker Park: 116 vacation rentals
  • Pilsen: 17 vacation rentals

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

What are the popular point of interests near where I can stay when traveling to Chicago?

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

  • Chicago Water Tower: 1,009 vacation rentals
  • Michigan Avenue: 1,008 vacation rentals
  • Chicago Theater: 1,009 vacation rentals
  • Chicago 107th Street Station (Beverly Hills): 952 vacation rentals
  • Chicago 87th Street Station (South Chicago): 978 vacation rentals

But there are many other points of interest around Chicago listed on VRBO 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. VRBO has 763 Condos/Apartments in Chicago. Our other popular types of vacation rentals in Chicago include:

  • Studios: 585 rentals available
  • Houses: 174 rentals available
  • Hotels: 36 rentals available

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

Can I rent downtown rentals in Chicago?

Absolutely, VRBO has 146 downtown rentals in Chicago. You have also many other possibilities in Chicago area, including:

  • Lake rentals: 72 rentals
  • Golf course rentals: 33 rentals
  • Village rentals: 18 rentals

Please use our search bar to access the selection of vacation rentals.

Can I find a vacation rental with private pool in Chicago?

Yes, you can select your prefered vacation rental with private pool among our 19 vacation rentals with private pool available in Chicago. Please use our search bar to access the selection of vacation rentals available.

    The exciting city of Chicago awaits you

    Come and experience Chicago and its architecture, theater scene and museums. This cosmopolitan and scenic city is known for its art, monuments and entertainment. Chicago Cultural Center, Ford Center for the Performing Arts Oriental Theatre and Chicago Theatre are a few of the top cultural sights. A vacation rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

    Sightseeing in and around Chicago

    Are you hoping to discover attractions to see in the area? Venture out of your vacation home and check out everything that makes Chicago a one-of-a-kind vacation spot. These are some of the major attractions to explore, all within 30 miles (48.2 km) of the city center:

    • Skydeck Ledge (0.4 mi / 0.6 km)
    • Navy Pier (1.2 mi / 1.9 km)
    • John G. Shedd Aquarium (1.2 mi / 2 km)
    • Adler Planetarium and Astronomy Museum (1.5 mi / 2.4 km)
    • Lincoln Park Zoo (2.7 mi / 4.4 km)
    • Brookfield Zoo (11 mi / 17.7 km)

    Exploring the natural landscape of Chicago

    Whether you're an active traveler or just want to spend some time taking in the scenery, Chicago is a great place to get out in nature. These are a few of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city center:

    • Millennium Park (0.2 mi / 0.4 km)
    • Grant Park (0.7 mi / 1 km)
    • Lincoln Park (4.8 mi / 7.8 km)
    • Chicago Riverwalk (0.5 mi / 0.8 km)
    • Ohio Street Beach (1.2 mi / 1.9 km)
    • Northerly Island Park (1.5 mi / 2.4 km)