Where to stay around Chicago?

Our 2018 accommodation listings offer a large selection of 1,159 holiday lettings near Chicago. From 868 Flats to 676 Studios, find unique self catering accommodation for you to enjoy a memorable stay with your family and friends. The best place to stay near Chicago for a long holiday or a weekend break 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 accommodations for a long holiday or just a weekend break in Chicago:

  • Chicago Loop: 456 holiday homes
  • Ukrainian Village: 248 holiday homes
  • Near West Side: 283 holiday homes
  • Roscoe Village: 206 holiday homes
  • Old Town: 185 holiday homes

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

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

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

  • Chicago 87th Street Station (Woodruff): 1,088 holiday lettings
  • Stage 773: 1,123 holiday lettings
  • Chicago 107th Street Station (Beverly Hills): 1,056 holiday lettings
  • Wrigley Field: 1,122 holiday lettings
  • Chicago Water Tower: 1,117 holiday lettings

But there are many other points of interest around Chicago listed on HomeAway 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 Flats in Chicago?

Yes, of course. HomeAway offers 868 Flats in Chicago. Our other popular types of Chicago holiday rentals include:

  • Studios: 676 self catering accommodations
  • Houses: 201 self catering accommodations
  • Hotels: 35 self catering accommodations

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

Can I find a holiday accommodation with pool in Chicago?

Yes, you can select your preferred holiday accommodation with pool among our 90 holiday homes with pool available in Chicago. Please use our search bar to access the selection of holiday rentals available.

    The vibrant city of Chicago awaits you

    Come and experience Chicago and its architecture, theatre scene and museums. This cosmopolitan and scenic city is well 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 holiday 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 holiday home and check out everything that makes Chicago a one-of-a-kind holiday spot. These are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

    • 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 traveller 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 centre:

    • 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)