Discover a selection of 1,000 vacation rentals in Downtown Chicago, US that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and parking. Prices start at $70 per night, and condos and townhouses are popular options for a stay in Downtown Chicago. Either way, you'll find a rental for everyone's needs.
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.

How many vacation rentals are available around Downtown Chicago, US?

Our 2020 property listings offer a large selection of 1,127 vacation rentals around Downtown Chicago. From 874 condo and apartment rentals to 11 townhouse rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

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 Vrbo travelers, the top most popular destinations to visit are:

  • Near North Side: 572 vacation rentals
  • The Loop: 622 vacation rentals
  • West Town: 527 vacation rentals
  • Lakeview: 233 vacation rentals
  • Lincoln Park: 525 vacation rentals

And Vrbo 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:

  • Oak Park: 1,215 rentals
  • Evanston: 961 rentals
  • Forest Park: 1,188 rentals
  • Glenview: 221 rentals
  • Tinley Park: 28 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, IL (MDW-Midway Intl.): 1,429 vacation rentals
  • Chicago, IL (ORD-O'Hare Intl.): 1,418 vacation rentals
  • Gary, IN (GYY-Gary - Chicago Intl.): 210 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?

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

  • Jackson Park: 1,117 rentals
  • Garfield Park: 1,425 rentals
  • United Center: 227 rentals
  • Highland Park: 467 rentals
  • Wrigley Field: 1,413 rentals

But there are many other points of interest around Downtown Chicago listed on Vrbo 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

Oak Park
1,215 vacation rentals
961 vacation rentals
Forest Park
1,188 vacation rentals
221 vacation rentals
Tinley Park
28 vacation rentals
74 vacation rentals
88 vacation rentals
667 vacation rentals
Des Plaines
219 vacation rentals
84 vacation rentals
74 vacation rentals
Elmwood Park
928 vacation rentals
Highland Park
467 vacation rentals
Orland Park
27 vacation rentals
307 vacation rentals
Burr Ridge
148 vacation rentals
94 vacation rentals
1,261 vacation rentals
Oak Lawn
131 vacation rentals
Calumet City
55 vacation rentals