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.


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 features

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)
How to get there

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.

How many vacation rentals are available around Chicago?

Our 2019 vacation rental listings offer a large selection of 1,868 house rentals around Chicago. From 1,477 Condos/Apartments to 301 Houses, find unique vacation rental for you to enjoy a memorable holiday or a weekend with your family and friends. The best place to stay around Chicago is on HomeAway.

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

Whether you're travelling 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: 826 vacation rentals
  • Magnificent Mile: 605 vacation rentals
  • Grand Crossing: 41 vacation rentals
  • North Center: 200 vacation rentals
  • Gold Coast: 246 vacation rentals

For other neighbourhoods, 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 travelling to Chicago?

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

  • Grant Park: 1,394 home rentals
  • Wrigley Field: 1,823 home rentals
  • Millennium Park: 1,358 home rentals
  • McCormick Place: 1,522 home rentals
  • Lookingglass Theatre: 1,822 home rentals

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 vacation rentals available near the point of interest of your choice.

Can I rent Condos/Apartments in Chicago?

Yes, of course. HomeAway has 1,477 Condos/Apartments in Chicago. Our other popular types of vacation rentals in Chicago include:

  • Houses: 301 lodging choices
  • Townhouses: 35 lodging choices
  • Cabins: 6 lodging choices

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

Can I find a vacation rental with pool in Chicago?

Yes, you can select your preferred vacation rental with pool among our 185 vacation homes with pool available in Chicago.

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