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 kitchens. Prices start at $110 per night, and townhouses and condos 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 783 vacation rentals around Downtown Chicago. From 19 townhouse rentals to 572 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent a city-center property in Downtown Chicago?

If you're into the thought of springing out of bed and finding yourself among vibrant shops, restaurants and attractions in minutes, then consider staying somewhere central. Vrbo has 148 centrally located rental homes available. Open to more ideas? Vrbo has oodles more rental options to look through, including:

  • 55 town vacation rentals.
  • 49 lakeside vacation rentals.
  • 42 lake-view vacation rentals.

Can I rent an apartment in Downtown Chicago?

There's no need to say goodbye to the conveniences of home just because you're going on vacation. Sit back and relax in your very own apartment and soak up the area like a local. You can choose from 1,048 different options via Vrbo. How does $49 a night sound? That's what you're looking at paying if you don't dilly dally! If that doesn't agree with your family's style, we have a range of other property types to select from, such as:

  • House: 191 vacation homes. Prices start from $50 per night.
  • Condo: 191 vacation homes. Prices start from $75 per night.
  • Hotel: 87 vacation homes. Prices start from $103 per night.

Can I stay in Downtown Chicago in a large group?

There's nothing more enjoyable than exploring somewhere new with family and friends. The good news is Vrbo has some places suitable for big groups. 257 apartment vacation homes are listed. Presently, they're the top choice here for large groups. Around the area, the properties that can accommodate bigger groups include:

  • On the lookout for vacation homes that can house 6 people? We have 376 that will suit. The prices start from $49 per night.
  • Require a rental property for 8 guests? We have 180 that will suit. Prices start from $80 a night.
  • Planning a trip away with a group of 5? We offer 135 vacation homes that will be perfect. Prices start from $75 per night.

You and all your buddies will be in good hands when you book your Downtown Chicago vacation through us!

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