Destination guide

Settle into the Windy City

With its glittering skyscrapers, jaw-dropping Art Deco architecture, cavernous museums, and pristine parks, downtown Chicago is the thrilling epicenter of one of North America's most iconic major cities. From the cutting-edge galleries of River North, to the exclusive designer boutiques of the Magnificent Mile, to the chic bars and clubs of Rush Street, you'll find endless diversions here, whatever your idea of a good time may be. And with an array of alluring downtown Chicago vacation rentals to pick from, you can find a home-away-from-home, right in the heart of the action.

Things to do

Amazing art all over downtown Chicago

You won't have to stray far from your downtown Chicago vacation rental to find awe-inspiring attractions. The Loop district is renowned for its eclectic public art installations, from Anish Kapoor's giant, bean-shaped steel sculpture, to Marc Chagall's surrealistic Four Seasons mosaic. For more masterpieces than you could ever hope to admire in a single sitting, head to the Art Institute of Chicago. One of the most prestigious museums in the United States, it's home to priceless works by the likes of Picasso, Edward Hopper, and Andy Warhol. For unbeatable panoramic views of the city, head up to the Skydeck of the vertigo-inducing Sears Tower.


Dine, drink, and dance in downtown Chicago

The Magnificent Mile is a shopaholic's mecca, home to a seductive array of department stores, fashion boutiques, and no-expense-spared flagship shops for many of the world's most popular retailers. Should you work up an appetite during your spree, you'll find an abundance of irresistible eateries nearby, where you can feast on everything from elegant fusion cuisine to decadent Chicago-style deep pan pizza. Once you've fueled up, it's time to explore the city's vibrant nightlife. Take it easy with an expertly mixed cocktail in a stylish jazz bar, or dance until the early hours in a pulsing house club.


Vibrant seasons in downtown Chicago

Chicago's climate is characterized by contrasts. Summer days tend to be long, hot and sunny, with humidity sometimes making things a little uncomfortable outside. June to August marks the city's peak visitor season, so downtown Chicago vacation rentals are naturally in high demand at this time of year. Fall can be a lovely time to visit, with milder temperatures and fewer out-of-towners jostling to see all the top sights. Spring weather is also usually pleasantly moderate, but rainfall in April and May can be high. Winters can be bitingly cold, with plenty of snowfall, so be sure to wrap up warm.

Natural features

From pristine parks to blissful beaches

An abundance of pristine parks and green spaces make it easy to escape the hustle and bustle of this teeming metropolis. The Lurie Garden is a true urban oasis, where you can marvel at dazzling seasonal flower displays. Sprawling Lincoln Park is home to a beautifully maintained city zoo, where you can get up close and personal with everything from playful penguins to majestic African lions. If you're visiting during the warmer months, be sure to check out one of the glorious lakefront beaches, where you can lounge on golden sand whilst admiring the city skyline.

Can I find a vacation rental around Downtown Chicago?

Yes, our 2019 property listings offer a large selection of 1,437 vacation rentals near Downtown Chicago. From 1,203 Condos/Apartments to 175 Houses, find the best place to stay with your family and friends to discover the Downtown Chicago area.

What are the most popular destinations to visit in Downtown Chicago?

There are many lovely places to stay for a holiday trip or just for a weekend in Downtown Chicago. From HomeAway travelers, the most popular destinations to visit are:

  • Indiana: 1,925 vacation rentals
  • Lake Michigan: 11,744 vacation rentals
  • Wrigleyville: 411 vacation rentals
  • Lincoln Park: 671 vacation rentals
  • Evanston: 1,207 vacation rentals

And HomeAway offers you the chance to discover many other popular destinations in Downtown Chicago! Please use our search bar to access the selection of vacation rentals available in other popular destinations.

What are the main cities to discover in Downtown Chicago?

Whether you're traveling with family or friends, here are the cities with the largest selection of vacation rentals for a holiday trip or just for a weekend in Downtown Chicago:

  • Evanston: 1,207 rentals
  • Oak Park: 1,493 rentals
  • Gary: 74 rentals
  • Tinley Park: 24 rentals
  • Rosemont: 287 rentals

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

Can I find easy-access vacation rentals when traveling by plane to Downtown Chicago?

Yes of course. Our owners offer a large selection of vacation rentals near airports. The airports with a large selection of vacation rentals in Downtown Chicago are:

  • Chicago Midway International Airport (MDW): 1,718 vacation rentals
  • O'Hare International Airport (ORD): 1,673 vacation rentals
  • Gary Chicago International Airport (GYY): 222 vacation rentals

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

Near which points of interest can I spend my holidays in Downtown Chicago?

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

  • Wrigley Field: 1,694 rentals
  • Grant Park: 1,294 rentals
  • Chicago Water Tower: 1,693 rentals
  • McCormick Place: 1,422 rentals
  • Navy Pier: 1,217 rentals

But there are many other points of interest around Downtown Chicago listed on HomeAway where you can find your place to stay. Just write your wanted destination in our search bar and have a look at our selection.

Explore destinations around Downtown Chicago

1,207 vacation rentals
Oak Park
1,493 vacation rentals
74 vacation rentals
Tinley Park
24 vacation rentals
287 vacation rentals
Des Plaines
221 vacation rentals
328 vacation rentals
Orland Park
28 vacation rentals
86 vacation rentals
461 vacation rentals
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Highland Park
48 vacation rentals
111 vacation rentals
Elmwood Park
1,266 vacation rentals
239 vacation rentals
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Oak Lawn
173 vacation rentals
120 vacation rentals
1,605 vacation rentals
Forest Park
1,373 vacation rentals