Discover a selection of 2,000 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 $120 per night, and houses and condos are popular options for a stay in Downtown Chicago. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Downtown Chicago
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.

What are the top vacation rentals in Downtown Chicago?

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:

  • "53th Floor Magmile Penthouse - Views": If you're after someplace in Near North Side with 2 bedrooms and the comforts of home, this getaway will tick your boxes. Amenities include a garage and a fitness facility.
  • "52nd Floor Magmile Penthouse - Views": Put your bags down and your weary feet up at this sought-after getaway in Near North Side. It comes with 1 bedroom, a garage, an ice maker and more.

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.

What are the top-rated vacation rentals for weekend getaways in Downtown Chicago?

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:

  • "51st Floor Magmile Penthouse - Views": This vacation rental in River North makes for a heavenly weekend getaway. Spend time exploring attractions like Addams/Medill Park and Mills Park, then slow down and kick back in your cozy pad. Off-street parking options and heating are among the amenities here.
  • "52th Floor Penthouse - Fireplace": An equally appealing choice, this getaway in River North features a living room, an oven and more. Coyote Run Golf Course and Monument Park are nearby when you need to get your fix of Mother Nature.

Can I find studio apartments for rent in Downtown Chicago?

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.

  • "52nd Floor Magmile Penthouse - Views" in Near North Side puts you within easy reach of some of the area's top cultural sights, including Ravinia Park and Citadel Theatre Company. A fireplace and a nearby zoo are two of the handy amenities here.
  • Alternatively, book a stay at "51st Floor Magmile Penthouse - Views" which comes with a pool, a kitchen and more. Located in River North, sights such as Park West and Holy Trinity Russian Orthodox Cathedral will appeal to your inner culture buff.

Can I find short term rentals in Downtown Chicago?

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?:

  • Close to the center of River North, "51st Floor Magmile Penthouse - Views" is suited to a short stay. Use it as a base to see interesting attractions nearby, including Wrigley Field and McCormick Place.
  • Come for the home comforts of "52th Floor Penthouse - Fireplace", stay for the unique sights scattered around it. This vacation rental in River North puts you near McCormick Place, Willis Tower and other highlights.

What are the best romantic weekend getaways in Downtown Chicago?

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:

  • Discover your inner Casanova at "53th Floor Magmile Penthouse - Views". This Near North Side getaway is ideal for romance, with amenities like a sauna and a fireplace to help set the mood.
  • Alternatively, organize an amorous weekend away at "52nd Floor Magmile Penthouse - Views". Located in Near North Side, it offers beauty services, a sauna and more.

What are the best houses for rent with a pool in Downtown Chicago?

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:

  • The pool at "Casa De Barqueiros - Six Bedroom House" will add another level of fun to your getaway. Located in West Loop Gate, this property also comes with a microwave oven and a kitchen.
  • Wake up and enjoy an early morning dip at "Holiday House Santaella For 1 - 6 Persons With 3 Bedrooms" in Greektown. A porch and a microwave oven are other amenities on offer here.

What are the best large family vacation rentals in Downtown Chicago?

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:

  • For family-friendly getaways in River North, "Views, Pool, Fireplace, Fitness Center" is a superb choice. It offers 3 bedrooms and can fit up to 8 people. A dining table and a DVD player are just two of the useful amenities you'll find here.
  • "Stunning 3bedroom Penthouse In The Loop | Roof Deck" in The Loop is another terrific option. It has the capacity to accommodate up to 8 guests and features 3 bedrooms. Coffee and tea making facilities and a toaster will help keep your gang happy and comfortable.

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.

What are the best large houses to rent with indoor pools in Downtown Chicago?

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:

  • Jump in, the water's great at "3b/2. 5ba Luxury Penthouse With Views". Located in The Loop, this exceptional haven has 3 bedrooms sleeping up to 8 guests. A kitchen and a swimming pool are a few other handy amenities that help make this place a winner.
  • Get set for plenty of relaxing and mingling by the indoor pool at "3b/3ba Luxury Sky Loft | Panoramic Views" in Near North Side. With 3 bedrooms, up to 8 friends or family members can tag along with you at this superb property. It's full of features to keep a large group happy, including a swimming pool and a kitchen.

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.

Are there one-bedroom vacation rentals in Downtown Chicago?

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:

  • Get away on your own or spend time with the fam at "52nd Floor Magmile Penthouse - Views" in River North. When you're not checking out nearby sights, make good use of a swimming pool and a fireplace.
  • Or, unpack your bags and make yourself at home at "51st Floor Magmile Penthouse - Views". A kitchen and a lake view are just a couple of the amenities available to use at this property in River North.

Can I find two-bedroom vacation rentals 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:

  • Unpack your bags at "53th Floor Magmile Penthouse - Views" in Near North Side and then venture out and explore what's around you. Amenities including a lake view and a swimming pool will help make your stay at this two-bedroom escape even more enjoyable.
  • "53/54th Floor Magmile Penthouse" is another excellent option. Take advantage of a lake view, a swimming pool and other conveniences at this River North property.