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.
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.
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.
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.
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.
From extravagant condos to intimate log cabins, Vrbo has properties to suit all sorts of tastes and budgets. Here are some of the top vacation rentals in Downtown Chicago:
For even more great options, use the search bar at the top of the page to find the perfect Downtown Chicago vacation rental for you.
If vacation homes were actors, these would be on the Hollywood Walk of Fame! For a wonderful weekend away in Downtown Chicago, make sure you check out the following options:
You'll find plenty of studio apartments in Downtown Chicago. Obviously they're no mansion, but they pack a big punch when it comes to convenience, character and location. Here are a few highly rated options.
Swap the generic hotel experience for the comfort and character of your own digs. Even if you only have a couple of days to get away, you'll find short-term rentals in Downtown Chicago that'll feel like your second home. Why not start with these?:
If you really want to dazzle your someone special, take them someplace special! Plan a romantic weekend getaway in Downtown Chicago at one of these escapes and let the sparks fly:
In Downtown Chicago, there are plenty of house rentals where every day can be a pool day. Having a splashing good time will be your highest priority at one of these sought-after getaways:
We have large family vacation rentals that'll fit almost everybody — yes, even those long-lost cousins of yours! Whatever type of property you want, you'll find one that suits on Vrbo. Here are our top picks in Downtown Chicago:
Searching for some excitement? There are tons of family-friendly attractions in Downtown Chicago to pick from, like Navy Pier and John G. Shedd Aquarium. Chicago Children's Museum is also a hit with visiting families.
Relaxation bliss for adults and good times on tap for kids, an indoor pool will add extra flair to your vacation. If you're chasing someplace spacious where you and your team can enjoy a dip, don't miss these magnificent large houses in Downtown Chicago:
If you want more inspiration and ideas, use the search bar at the top of the page and adjust the filters to see our full range of Downtown Chicago vacation rentals.
If you're traveling alone or with a few others and don't need a whole lot of space, a single-bedroom vacation rental has your name all over it. Take a break and enjoy the comforts of home at one of these properties in Downtown Chicago:
Whether you're chasing a two-bedroom property for an extended getaway or just a weekend, we'll help you find the perfect pad. Here are some of our favorite options in Downtown Chicago for you to consider: