Destination guide

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.

Activities

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)
Natural highlights

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)
Transport

How to get to and around Chicago

Fly into Chicago, IL (MDW-Midway Intl.), the closest airport, located 8.6 mi (13.9 km) from the city center. If you can't find a flight that works for your travel itinerary, you can also fly into Chicago, IL (ORD-O'Hare Intl.), which is 15.7 mi (25.3 km) away.

If you're traveling by train, Millennium Station, Chicago Van Buren Street Station and Chicago Union Station are the main stations in the area. You can get around Chicago by jumping on the metro at Monroe Station, Monroe Station or Adams-Wabash Station.

Where to stay around Chicago?

Our 2019 accommodation listings offer a large selection of 1,413 holiday lettings near Chicago. From 1,095 Condos/Apartments to 244 Houses, find unique self catering accommodation 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 accommodations for a long holiday or just a weekend break in Chicago:

  • Wicker Park: 591 holiday homes
  • West Bucktown: 103 holiday homes
  • Gold Coast: 200 holiday homes
  • Magnolia Glen: 30 holiday homes
  • Riverdale: 123 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:

  • Walt Disney House: 1,396 holiday lettings
  • Elmwood Park Mont Clare Station: 1,394 holiday lettings
  • Niles Edison Park Station: 1,376 holiday lettings
  • United Center: 1,373 holiday lettings
  • Museum Campus: 1,366 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 Condos/Apartments in Chicago?

Yes, of course. HomeAway offers 1,095 Condos/Apartments in Chicago. Our other popular types of Chicago holiday rentals include:

  • Houses: 244 self catering accommodations
  • Townhouses: 34 self catering accommodations
  • Cabins: 4 self catering accommodations

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

Can I find a holiday accommodation with pool in Chicago?

Yes, you can select your preferred holiday accommodation with pool among our 139 holiday homes with pool available in Chicago. Please use our search bar to access the selection of holiday rentals available.

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