Destination guide

Blow your mind in the windy city

Set on the southern shore of Lake Michigan in America's Midwest, Chicago is the hub of, well, everything. Foodies come for the fine dining, both casual and chic. Culture hounds flock to the impressive museums, gape at the stunning architecture, and snap selfies with one of the world's most beautiful skylines in the background. Sports fans freak out over their favorite teams. Music fans and families get their fill of summer festivals, parks and public art. Chicago vacation rentals are in demand year-round for good reason. Welcome to what Norman Mailer called the Great American City.

Things to do

Take a day off in the style of Ferris Bueller

There's a reason Ferris and his friends ended up at the Art Institute of Chicago. Its collection of Impressionist, modern and classical works are unrivalled in the region. Three other cultural hotspots are all within a mile of each other: the Shedd Aquarium, where students hope they're going on their next field trip, the Field Museum of Natural History featuring Egyptian artifacts and dinosaur skeletons, and the Adler Planetarium, with its kid-friendly exhibits and astronomy shows. When you get sick of the indoors, head to the Lincoln Park Zoo.


A "Second City" that's second to none, thank you very much

Chicago got its nickname Second City when it was the nation's 2nd largest. Now it's America's 3rd city in terms of population but its 1st in sight-seeing. For a bird's-eye view, you can tool around on the city's historic elevated rail, or head to Willis Tower's Skydeck Chicago or the John Hancock Center's 360 CHICAGO Observation Deck. Get a closer look at architectural wonders with a visit to Frank Gehry's Pritzker Pavilion or Frank Lloyd Wright's Robie House. Chicago vacation rentals are a particularly good choice in spring, summer and fall, when visitors rock out at music festivals in Millennium Park.


Don't let the wind keep you away from the windy city

Chicago's climate breeds 4 distinct seasons, and you're welcome to try them all. Vacationers like to come in summer, when temps range from the 50s to 80s, and outdoor activities are most popular. Chicago vacation rentals will be at their most expensive then, but the summer sun and fun might be worth it. Then again, can't complain about spring and autumn, when the temperatures cool and there are fewer crowds. If you want to save a buck and have lots or warm layers, or if you're willing to hang out in great museums all day, winter is your sweet spot.

Natural highlights

Chi-town is a fly town for natural wonders, too

There's so much urban culture and cool in Chicago, you can be forgiven for forgetting that it's set along a giant freshwater lake. Chicago has great beaches where everyone can swim at no charge. There are plenty of waterfront parks to enjoy when the weather is too cold for swimming, and the parks further inland are a sight to behold. The most famous is Millennium Park, but the little ones and nature lovers in your party will appreciate a visit to Midway Park, where you can skate in winter and stroll the gardens all year.

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 centre. 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 travelling 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 near Chicago?

Our 2019 accommodation listings offer a large selection of 1,414 holiday rentals near Chicago. From 1,096 Condos/Apartments to 244 Houses, find unique holiday homes 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 rentals for a long holiday or just a weekend break in Chicago:

  • Gold Coast: 203 holiday homes
  • Lakeview: 310 holiday homes
  • Sheffield Neighbors: 98 holiday homes
  • Rush & Division: 213 holiday homes
  • West Bucktown: 104 holiday homes

For other neighbourhoods, please use our search bar to access the selection of holiday homes 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 homes near great places in Chicago. From HomeAway travellers, the most popular points of interest to stay near are:

  • Swedish Covenant Hospital: 1,376 holiday rentals
  • Chicago 79th Street Station (Cheltenham): 1,368 holiday rentals
  • Chicago McCormick Place Station: 1,372 holiday rentals
  • Chicago's Mercury Theater: 1,375 holiday rentals
  • Crown Fountain: 1,366 holiday 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 holiday rentals available near the point of interest of your choice.

Can I rent Condos/Apartments in Chicago?

Yes, of course. HomeAway offers 1,096 Condos/Apartments in Chicago. Our other popular types of Chicago holiday rentals include:

  • Houses: 244 holiday houses
  • Townhouses: 34 holiday houses
  • Cabins: 4 holiday houses

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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