Chicago Vacation Rentals, Illinois: house rentals & more

Discover a selection of 1315 homes, 1923 apartments, and other vacation rentals in Chicago that are perfect for your trip. Whether you’re staying in a vacation home with friends, family, or even just your pets, you'll have the amenities you expect and more, which might include parking and a hot tub. Whatever you're looking for, you'll be able to choose a rental for everyone's needs, including a place that's non-smoking or offers accessibility.

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Find properties near top attractions in Chicago

Michigan Avenue

Find the best place to stay - Chicago

Rare Gem! Indoor Pool, Rooftop Deck, Close to Magnificent Mile

Sleeps 2 · 1 bedroom · 1 bathroom

Top rated rentals - Chicago

Cozy living room equipped with games, Nintendo Wii, smart TV & fold down couch.

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Wicker Park

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Discover Chicago

Chicago vacation rentals

Book Chicago vacation rentals and explore the Windy City's plethora of cultural attractions. Sprawling along the shores of Lake Michigan, Chicago is renowned for its jazz and blues music, deep-dish pizza, and bold skyline. Be sure to visit the iconic Art Institute of Chicago. This historic gallery is home to some of the world's most significant works of art. Meanwhile, the Museum of Science and Industry showcases Chicago's innovative side.

For refreshing strolls, the Riverwalk is a must. Surrounded by skyscrapers, this waterfront promenade is dotted with trendy cafés, bars, and restaurants. A short walk away, you'll encounter Millennium Park. Chicago's green oasis hosts a multitude of events all year round, from music festivals in summer to ice skating in winter.

Is Chicago good for vacation rentals?

Take your pick from hundreds of Chicago vacation rentals and set the stage for your escape to the Windy City. No matter your preferences, vacation homes in Chicago come in all shapes and sizes. From trendy apartments in Wrigley Field to modern condos in McCormick Place, on Vrbo you'll find a great short-term rental in Chicago. Then there are the amenities: Pools, spas, air conditioning, and more are just some of what you'll get with Chicago vacation rentals.

When is the most popular time of year to visit?

Among the most popular times to stay in Chicago vacation rentals are the summer months from May to August. Warm weather makes it an ideal time to explore the city's green spaces. There's also a variety of exciting festivals and events taking place, too.

When is the cheapest time of year to visit?

One of the cheapest periods to stay in a vacation rental in Chicago is between January and March. The winter typically sees fewer tourists in town. This lower demand means you can often bag great deals and save on your vacation home in Chicago.

Find vacation homes in Chicago offering discounts

In Chicago you can often discover great deals and discounts on Vrbo, especially for newly listed homes as well as weekly or monthly vacation rentals. Whether you’re planning a short getaway or an extended stay, Vrbo offers a variety of options to suit your needs and budget.

Frequently asked questions

What is the best area to stay in Chicago when booking a vacation rental?

One of the more sought-after locations to get a vacation home in Chicago is Near North Side. Spend your vacation here and you'll be a short distance from some top attractions including Navy Pier and Chicago Childrens Museum.

What is the most popular type of vacation rental accommodation in Chicago?

The most popular types of vacation rentals in Chicago are apartments. Looking for something different? Vrbo has many options to match the needs of our guests, so you'll see properties in lots of shapes and sizes. The ideal fit is waiting for you — lock in yours today.

How much does it cost to rent a vacation rental in Chicago?

Several things affect what you'll pay for a vacation rental in Chicago, including the season, length of stay and type of property. However, all our vacation homes have one thing in common — exceptional value. Simply add your travel dates to find your dream escape.

How much does it cost to rent a beach house in Chicago?

The average price for a vacation home near the beach in Chicago depends on when you're traveling and the type and size of property you're looking for. You can find prices easily and quickly on Vrbo by entering your destination and preferred travel dates. Then use our handy filter tool to select the number of bedrooms and amenities that you need, like WiFi, a pool and air conditioning.

Are there pet-friendly vacation rentals in Chicago?

With 1,659 properties that host four-legged guests, your furry buddy can also come along on your Chicago break. Use the filter tool to browse our pet-friendly vacation rentals and find the pawfect pad on Vrbo.

Can I rent a house with a pool in Chicago?

Pack your swimsuit and inflatable swan, because there are 307 houses with a private pool in Chicago. Stay at one of these superb vacation rentals and every day will be a pool day. Simply enter your dates into Vrbo, then use the "pool" filter to find the perfect place to make a splash!

What are popular rental amenities in Chicago?

When it comes to rental amenities that people are looking for in Chicago, a chef, a fireplace and a nearby waterfront rank the highest. With Vrbo vacation rentals, you'll have options to suit your style and taste, whether you're planning to get away with family members, friends or even pets.

Are there large group vacation rentals in Chicago?

With 131 properties that can host 10 or more guests in Chicago, there's no need to keep anyone off the invite list. From family vacations to special events like Christmas and birthday parties, Vrbo can help you find a large group rental to match the occasion.

Are there vacation rentals in Chicago that welcome kids?

Chicago has 1,646 family-friendly vacation rentals to choose from. And securing a stay that welcomes youngsters is super easy with our "Properties good for families" filter. As well as having the entire place to yourselves, you can also look forward to perks and amenities such as multiple bedrooms, pools and kitchens.

What are the top attractions for families in Chicago?

Keep your kids occupied at these popular family-friendly attractions in Chicago:

Navy Pier
Chicago Riverwalk
Shedd Aquarium

Are there one-bedroom vacation rentals in Chicago?

There are 577 one-bedroom properties in Chicago to choose from. A one-bedroom vacation home is an excellent choice if it's just two of you or if you're traveling alone. Toss in more space, convenience and privacy than a regular hotel, and you've got the makings of a break to remember.

Can I find two-bedroom vacation rentals in Chicago?

Gather your nearest and dearest and enjoy total privacy and comfort in one of the 442 two-bedroom vacation homes Chicago has to offer.