Chicago Vacation Rentals, Illinois: house rentals & more

Discover a selection of 1262 homes, 2490 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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Condo/Apartment

Find properties near top attractions in Chicago

Wrigley Field

Find the best place to stay - Chicago

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

Sleeps 2 · 1 bedroom · 1 bathroom

Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking

Sleeps 5 · 2 bedrooms · 2 bathrooms

Top rated rentals - Chicago

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Enjoy full kitchens, laundry, pools, yards and more
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More space, more privacy, more amenities — more value
A place for everyone
We stand for diversity, inclusion and families everywhere.
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Find out more about Chicago

Why visit Chicago

Architectural Wonders: Discover Chicago's iconic skyline with stunning architecture, including the Willis Tower and John Hancock Center.
Lakefront Bliss: Enjoy miles of beautiful beaches and scenic parks along Lake Michigan, perfect for outdoor activities.
Cultural Richness: Immerse yourself in vibrant neighborhoods like Little Italy and Wicker Park, showcasing diverse art and cuisine.
Chicago Riverwalk: Stroll along the picturesque Riverwalk, offering dining, shopping, and beautiful views of the city.
Family-Friendly Activities: Visit top attractions like the Field Museum and Lincoln Park Zoo for unforgettable family fun.

Popular types of accommodation in Chicago

Discover the vibrant city of Chicago with a variety of vacation rentals tailored to your needs. From modern apart hotels to cozy houses, there’s something for everyone. Whether you're looking for spacious apartments or charming holiday apartments, our platform offers the best Chicago vacation rentals to enhance your stay. Choose the perfect accommodation in Chicago and experience the Windy City like never before!

Apartments: The top choice for vacation rentals in Chicago, offering a variety of styles and amenities for a comfortable stay in the city.
Houses: A popular option for families and groups, providing spacious accommodations and a home-like atmosphere.
Condos: A favored selection featuring modern living spaces, often with great views and access to local attractions.
Cottages: A charming and cozy retreat ideal for those seeking a peaceful getaway.
Resorts: Offering luxurious amenities and recreational activities, perfect for travelers wanting a full-service experience.**

Top attractions in Chicago

Chicago offers a vibrant mix of family-friendly activities, outdoor adventures, and urban experiences. Explore beautiful urban parks, visit modern colleges and universities, and enjoy the scenic beaches. Don't miss shopping in the city, immersing yourself in its rich culture, and strolling along the Chicago Riverwalk. With plenty of outdoor activities, Chicago is an ideal destination for a memorable vacation experience.

Michigan Avenue: Known as the "Magnificent Mile," this bustling street is lined with high-end shops, restaurants, and iconic architecture, embodying the vibrant city life of Chicago.
McCormick Place: As the largest convention center in North America, McCormick Place hosts major conferences and events, showcasing a blend of business and innovation in a dynamic environment.
Navy Pier: This scenic jetty offers stunning views of Lake Michigan, a variety of attractions, art installations, and a friendly atmosphere perfect for family outings and leisurely strolls.

Things to do recommended for couples

Planning a romantic getaway in Chicago? Enjoy a lively concert at the Aragon Ballroom, savor a medieval dining experience at Schaumburg Medieval Times, and indulge in luxury at Chevy Chase Country Club. Each venue offers a unique vibe perfect for couples seeking memorable moments together.

Things to do recommended for families

Your family will have a blast at Wrigley Field, soaking in the sports atmosphere. Dive into fun at Great Wolf Lodge Water Park, filled with adventure and entertainment. For a relaxing day, explore the serene Northerly Island Natural Area, perfect for wellness and relaxation.

Things to do recommended for groups

Groups visiting Chicago can experience the vibrant arts scene at the historic Chicago Theatre, shop and dine at Gurnee Mills, and enjoy interactive fun at LEGOLAND® Discovery Center, all while soaking up the city's unique culture and entertainment offerings.

What do I need to keep in mind when booking a vacation in Chicago

When traveling with a group, family, or pets, or if you're considering extended stays, it's important to prioritize your needs when searching. Here are some helpful Vrbo booking tips to guide you.

Traveling to Chicago with a group: Think about how many bedrooms you require, as well as features like a full kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and many more on Vrbo.
Traveling to Chicago with young kids: Traveling with young kids can be quite demanding. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
Taking your pets with you to Chicago: For many families, a vacation wouldn’t feel complete without their furry companions. If that resonates with you, take a look at Vrbo listings that welcome pets. Many of these pet-friendly properties offer amenities like feeding bowls and beds, ensuring that all members of the family feel comfortable and at home.
Planning for a long term stay visiting Chicago: If you're in search of vacation rentals with discounts for month-long stays, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search options as well.

Where to stay in Chicago

Chicago and its surrounding areas offer a vibrant mix of urban energy and natural beauty, perfect for family vacations and outdoor adventures. Explore the charming streets of Little Italy, enjoy miles of stunning lakefront, and embrace the artistic vibe of Wicker Park. Whether you're seeking a friendly atmosphere or a romantic getaway, this city and its neighborhoods provide an unforgettable experience for all travelers.

Chicago: Chicago, known as the Windy City, is a vibrant metropolis that offers a rich blend of culture, history, and entertainment. Located along the shores of Lake Michigan, this city is famous for its stunning architecture, diverse neighborhoods, and iconic deep-dish pizza. Visitors can explore the bustling downtown, take in a show at one of the many theaters, or enjoy a game at a local sports facility. Chicago’s parks and waterfront areas provide ample opportunities for outdoor activities and family fun, making it a perfect destination for travelers of all ages.
Downtown Chicago: Downtown Chicago is the heart of the city, where urban excitement meets cultural richness. This bustling area is home to a myriad of attractions, including the Art Institute of Chicago, Millennium Park, and the famous Willis Tower Skydeck. With a plethora of shopping options, dining experiences, and entertainment venues, Downtown Chicago is ideal for those looking to immerse themselves in city life. The vibrant atmosphere and easy access to public transportation make it convenient to explore nearby neighborhoods and landmarks, ensuring an unforgettable travel experience.
Magnificent Mile: The Magnificent Mile is a premier shopping and dining district that runs along Michigan Avenue. This iconic stretch features high-end boutiques, popular department stores, and diverse restaurants, catering to all tastes. Beyond shopping, visitors can enjoy cultural attractions such as the John Hancock Center and the Chicago Riverwalk. The Magnificent Mile is a perfect blend of urban experience and outdoor leisure, offering scenic views and lively street life. Whether you’re looking to indulge in retail therapy or savor a delicious meal, this neighborhood is a must-visit during your Chicago getaway.

Best time to go to Chicago

If you're planning a trip to Chicago, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like January to February and November tend to have fewer bookings and better deals.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	25.7°F (-3.5°C)	Light Rain	Mostly Cloudy	Moderately Low	Slightly Low
February	27.0°F (-2.8°C)	Light Rain	Mostly Cloudy	Moderately Low	Slightly Low
March	37.0°F (2.8°C)	Light Rain	Mostly Cloudy	Average	Average
April	46.0°F (7.8°C)	Light Rain	Mostly Sunny	Average	Slightly Low
May	57.0°F (13.9°C)	Light Rain	Mostly Sunny	Moderately High	Slightly High
June	67.3°F (19.6°C)	Light Rain	Mostly Sunny	Moderately High	Slightly High
July	73.4°F (23.0°C)	Light Rain	Mostly Sunny	Moderately High	Average
August	73.0°F (22.8°C)	Light Rain	Mostly Sunny	Average	Average
September	67.1°F (19.5°C)	Light Rain	Mostly Sunny	Average	Average
October	54.9°F (12.7°C)	Light Rain	Mostly Sunny	Average	Slightly High
November	42.3°F (5.7°C)	Light Rain	Mostly Sunny	Average	Average
December	33.1°F (0.6°C)	Light Rain	Mostly Cloudy	Moderately Low	Average

Booking with Vrbo is simple

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate. Additionally, extending your stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental.

Save more with One Key

When you reserve a qualifying Vrbo for your group getaway, you'll receive OneKeyCash™ on the full booking amount. It truly benefits those who take the lead in organizing! Enroll in our One Key rewards program to unlock special member discounts and earn OneKeyCash™ on eligible stays. Sign up today and begin accumulating rewards!

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a user-friendly platform where you can easily plan new trips, resume your previous activities, and manage your travel arrangements. You’ll see your saved or booked properties organized into categories like Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties booked during 2023 and 2024.

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?

Snap up your vacation home in Near North Side and you’ll be based in one of Chicago’s most popular neighborhoods. Navy Pier and Chicago Children’s Museum are two of the major attractions here that’ll keep you busy during your visit.

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

Apartments are the most popular style of vacation rental in Chicago, according to our data. Even if you have a different idea about what you’d like, Vrbo has properties in all sizes and shapes. Filter our options to find your ideal fit.

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

Several factors determine how much you pay for a vacation rental in Chicago, such as the time of year, property type and length of stay. Still, all our vacation homes have one thing in common — exceptional value. Simply add your travel dates to find your ideal fit.

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

Prices for beach houses in Chicago can vary depending on the size and style of the property and when you plan to travel. Simply enter your travel dates into Vrbo and how many guests to see your rental options and prices. From there you can use our filter tool to narrow your search by ratings, nearby activities and more.

Are there pet-friendly vacation rentals in Chicago?

Good news. There are. You’ll find 2,617 stays that roll out the welcome mat in Chicago on Vrbo. Our furry best friends need a break too, so simply use our search function for pet-friendly vacation rentals to book a property where your puppy can be near his favorite humans.

Can I rent a house with a pool in Chicago?

Grab your swimsuit and goggles, because there are 663 houses with a private pool in Chicago. Unwind at one of these popular vacation rentals and enjoy a pool day every day. Simply enter your dates into Vrbo, then use the “pool” filter to find the perfect place for a splashing good time!

Are there vacation rentals in Chicago that welcome kids?

Chicago has 2,575 family-friendly vacation rentals to choose from. And finding a stay that welcomes children is super easy with our “Properties good for families” filter. Besides having the whole place to yourselves, you’ll have access to perks and amenities such as dining rooms, kitchens and pools.

What are the top attractions for families in Chicago?

Keep the kids entertained at these popular family-friendly attractions in Chicago:

Ernest Hemingway Museum and House
Anna and Frederick Douglass Park
Vietnam Veterans Memorial

Are there vacation rentals with WiFi in Chicago?

Whether you want to keep up to date with the news, look over emails or update your social media accounts, there are 1,035 vacation homes with WiFi in Chicago. Check the “WiFi” box when searching on Vrbo and stay connected on your vacation.

How can I find vacation rentals with air conditioning in Chicago?

Chicago has 2,365 vacation rentals where you’ll be able to kick back in air-conditioned comfort. To book a stay on Vrbo that has this perk, enter your desired travel dates and use the filters to select the “air conditioning” box.

How old do you have to be to rent a vacation rental in Chicago?

The age limit can differ between properties on Vrbo, so double-check the rules of the vacation rental in Chicago you’re considering. But in general, it’s 16, 18 or 21.

How long can I rent a vacation rental in Chicago for?

The amount of time you can stay in a Chicago vacation rental for is down to the property. Just tap in your preferred travel dates to find available options offering extended stays. They have all you need to make your extended break more comfortable and enjoyable, such as laundries and air conditioning. Some Vrbo vacation rentals may also offer weekly or monthly discounts, so you can stay even longer for less.

Does Vrbo offer discounts for vacation homes in Chicago?

Weekend adventure or extended escape, Vrbo has some incredible bargains and discounts in Chicago that’ll match your style and budget. Browse our weekly and monthly discounts on vacation rentals, or check out what’s just been added with one of our newly listed homes. Whatever you’re after, you’ll find the ideal place to stay — without spending a fortune.