Chicago vacation rentals

We found 4,711 vacation rentals — enter your dates for availability

Discover a selection of 945 homes, 1638 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.

Vacation rentals with weekly discounts - Chicago (and vicinity)

Showing deals for:Jun 19 - Jun 26

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9.2 out of 10, Wonderful, (21 reviews)
Wonderful
(21 reviews)

Beautiful and Cozy With 5 Bedrooms

Zion

8% off
Price is $453
$3,168 for 7 nights
All fees included
Beautiful and Cozy With 5 Bedrooms

Find spaces that suit your style

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    Enjoy full kitchens, laundry, pools, yards and more

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Find out more about Chicago

Why visit Chicago

  • Cultural Experiences: Immerse yourself in Chicago's rich arts scene, with museums, theaters, and live music venues showcasing local talent.
  • Urban Parks: Enjoy the city's beautiful parks and beaches, perfect for outdoor activities and family-friendly outings.
  • Diverse Neighborhoods: Explore the unique vibes of different neighborhoods, each offering its own charm, dining, and shopping options.
  • Stunning City Views: Take in breathtaking views of the skyline from iconic locations like the Willis Tower and rooftop bars.
  • Comfortable Accommodations: Choose from a variety of vacation rentals, from cozy apartments to spacious homes, tailored to your needs.

Popular types of accommodation in Chicago

Planning a trip to Chicago? The next step is picking the perfect place to stay. From stylish apartments to spacious houses and modern condos, Chicago offers a variety of vacation rentals to suit your needs. Discover ideal house rentals and apartment options that provide comfort and convenience, ensuring you have an unforgettable experience in the Windy City.

  • Apartments: The top choice for vacation rentals in Chicago, offering a variety of styles and amenities suitable for all travelers.
  • Houses: A popular option for those seeking a home-like experience, ideal for families or groups wanting extra space.
  • Condos: These properties provide a blend of hotel-like features and residential comfort, perfect for a city stay.
  • Cottages: Charming and cozy, these rentals offer a unique getaway experience, often with a homey feel.
  • Villas: Elegant accommodations that provide luxury and spaciousness for a relaxing vacation experience.**

Top attractions in Chicago

Chicago is ideal for family-oriented and outdoor-themed vacations, offering a rich blend of attractions like urban parks, beaches, and medical centers. Visitors can enjoy cultural experiences and family-friendly activities while exploring the city’s vibrant streets and shopping districts. From leisurely beach outings to engaging in the local culture, Chicago provides a diverse range of experiences for every traveler.

  • Naval Base Great Lakes: This military installation offers a unique glimpse into naval training and operations, featuring friendly personnel and family-friendly events. It provides a sense of community and patriotism.
  • Michigan Avenue: Known as the Magnificent Mile, this bustling street is lined with shops, restaurants, and cultural landmarks, showcasing the vibrant city atmosphere and architectural beauty of Chicago.
  • Navy Pier: A lively jetty featuring entertainment, dining, and stunning lakefront views, Navy Pier is perfect for leisurely strolls and family-friendly activities, all set against a picturesque urban backdrop.

Things to do recommended for couples

Planning a romantic getaway in Chicago? Indulge in luxury at Chevy Chase Country Club, Bridges of Poplar Creek Country Club, or Ravinia Green Country Club. Enjoy exquisite dining, beautiful landscapes, and intimate settings perfect for couples looking to create unforgettable memories together.

Things to do recommended for families

Families will love exploring the interactive exhibits at the Museum of Science and Industry, visiting the adorable animals at Lincoln Park Zoo, and enjoying a day at Navy Pier with its rides and games. Don’t miss the Shedd Aquarium for an unforgettable underwater adventure.

Things to do recommended for groups

Groups visiting Chicago can enjoy a thrilling architectural boat tour along the Chicago River, explore the vibrant art scene in the West Loop, and savor deep-dish pizza together at a local favorite. Don’t miss the chance to experience the lively atmosphere at Millennium Park.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

If you're traveling with a group, family, or pets, or if you're seeking longer stays, it's important to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to consider.

  • Traveling to Chicago with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for all these options and more on Vrbo.
  • Traveling to Chicago with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, think about how close you are to family-friendly attractions.
  • Taking your pets with you to Chicago: For many families, a vacation wouldn't be the same without their furry companions. If that resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly properties come equipped with feeding bowls and comfortable beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Chicago: If you're in search of vacation rentals that offer great deals for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider adding features like a parking space, a well-equipped kitchen, or a private pool to enhance your search.

Where to stay in Chicago

Chicago offers a vibrant blend of urban excitement and scenic beauty, making it a perfect vacation spot for families and couples alike. Explore downtown attractions, enjoy stunning city views, and relax in family-friendly neighborhoods. Whether you're seeking cozy vacation homes or thrilling city experiences, Chicago's welcoming atmosphere and friendly locals will ensure an unforgettable stay. Don't miss the chance to discover the unique vibes of this metropolis and its charming surroundings.

  • Chicago: Known as the Windy City, Chicago is a bustling metropolis that offers a diverse range of experiences for travelers. This city is famous for its stunning architecture, vibrant arts scene, and rich history. Visitors can explore Millennium Park, home to the iconic Cloud Gate sculpture, or catch a game at one of the local sports stadiums. The city's shopping districts, such as the Magnificent Mile, are perfect for those looking to indulge in retail therapy. With its lively theater scene and numerous outdoor spaces, Chicago is an ideal destination for families and city enthusiasts alike.
  • Arlington Heights: Located just a short train ride from downtown Chicago, Arlington Heights is a charming suburb known for its family-friendly atmosphere and thriving downtown area. Visitors can enjoy shopping at the Arlington Heights Town Square or catch a show at the historic Metropolis Performing Arts Centre. The suburb also features beautiful parks and recreational facilities, making it perfect for outdoor activities. With its mix of suburban tranquility and easy access to the excitement of Chicago, Arlington Heights is an excellent choice for those seeking a balanced vacation experience.
  • Downtown Chicago: As the vibrant core of the city, Downtown Chicago is a must-visit for all travelers. This area is home to iconic landmarks, including the Willis Tower and the Art Institute of Chicago. Visitors can explore the bustling streets filled with shops, restaurants, and cultural attractions. The nearby Chicago Riverwalk offers scenic views and recreational activities, while venues like the Chicago Theatre provide a taste of the city's rich performing arts scene. With its blend of urban energy and family-friendly attractions, Downtown Chicago is perfect for anyone looking to experience the essence of the city.

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 March tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January25.7°F (-3.5°C)Light RainMostly CloudyModerately LowSlightly Low
February27.0°F (-2.8°C)Light RainMostly CloudyModerately LowSlightly Low
March37.0°F (2.8°C)Light RainMostly CloudyModerately LowSlightly Low
April46.0°F (7.8°C)Light RainMostly SunnyAverageAverage
May57.0°F (13.9°C)Light RainMostly SunnyAverageAverage
June67.3°F (19.6°C)Light RainMostly SunnyModerately HighSlightly High
July73.4°F (23.0°C)Light RainMostly SunnyModerately HighSlightly High
August73.0°F (22.8°C)Light RainMostly SunnyModerately HighSlightly High
September67.1°F (19.5°C)Light RainMostly SunnyAverageAverage
October54.9°F (12.7°C)Light RainMostly SunnyAverageAverage
November42.3°F (5.7°C)Light RainMostly SunnyAverageAverage
December33.1°F (0.6°C)Light RainMostly CloudyAverageAverage

Booking with Vrbo is simple

Looking to save on your next vacation? Consider being flexible with your travel dates, as this can help you find better prices. Additionally, extending your stay can lead to 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. We're here to help you make your travel planning as smooth and cost-effective as possible.

Vrbo Trips: Planning made easy

Vrbo's Trip Board provides a convenient area for you to plan new trips, manage your existing plans, or review and organize your reservations. Your saved or booked properties are now categorized into Potential, Upcoming, or Current Trips for easier access. To check out Trip Boards, please visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

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, Illinois, United States of America when booking a vacation rental?
When considering the best area to stay in Chicago for a vacation rental, the River North neighborhood stands out as an excellent choice. Known for its vibrant art scene, River North is home to numerous galleries and is just a short walk from the renowned Magnificent Mile, where you can enjoy upscale shopping and dining. The area boasts a variety of vacation rental options, ranging from stylish lofts to modern apartments, suiting different tastes and budgets.

Another fantastic option is the Lincoln Park neighborhood, which offers a lovely blend of urban and natural attractions. Here, you can explore the beautiful Lincoln Park Zoo, which is free to the public, and take a leisurely stroll along the scenic paths of Lincoln Park itself. This area also features charming boutiques and a variety of restaurants, making it a delightful spot for visitors. The range of properties available in Lincoln Park often includes cozy homes and chic condos, providing a comfortable base for your Chicago adventures.
How much does it cost to rent a vacation home in Chicago?
Prices for vacation rentals in Chicago vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Chicago to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Chicago vacation house rentals?
You can find great discounts on house rentals in Chicago on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Chicago?
For renting a beach house in Chicago, the best areas are along the shoreline of Lake Michigan, particularly in neighborhoods like Rogers Park and Hyde Park. In Rogers Park, you'll find vacation homes and condos close to the beach, with amenities like private balconies overlooking the lake, outdoor grills, and easy beach access. This neighborhood is known for its diverse community and vibrant setting, with nearby parks and local cafes adding to its charm.

Hyde Park offers another excellent option, particularly around the scenic Promontory Point, where you can find rentals featuring spacious living areas, modern kitchens, and access to communal green spaces. This area not only provides stunning views of the lake but is also rich in culture and history, with attractions like the Museum of Science and Industry and the University of Chicago nearby.

Further south, the South Shore neighborhood presents opportunities for renting larger homes that are great for family gatherings. Many of these properties come equipped with amenities such as game rooms, private yards, and fire pits, making them ideal for enjoying summer evenings outdoors. The area also has parks and recreational facilities, enhancing the beach-going experience. Find your rental near the beach in Chicago.
What is the most popular type of vacation rental accomodation in Chicago?
In Chicago, apartments are the most popular type of vacation rental, with approximately 2,526 available in various neighborhoods, including the bustling River North and the historic Lincoln Park. These apartments typically feature modern amenities such as fully equipped kitchens, spacious living areas, and often access to fitness centers or rooftop terraces for enjoying city views.

For those seeking more space, around 1,046 vacation houses are also available, making them a great choice for families or larger groups. These homes generally offer multiple bedrooms, private yards, and outdoor seating areas, providing a comfortable setting for gatherings. Additionally, there are about 278 condos and a few cottages and villas, though these options are less common.
Are there any family house rentals in Chicago?
In Chicago, there are numerous family-friendly house rentals available, with around 1,589 options scattered throughout the city. Neighborhoods like Lincoln Park and Lakeview are particularly popular among families, offering spacious homes with convenient access to parks, playgrounds, and local attractions. Many of these properties come equipped with full kitchens, large living areas great for gatherings, and outdoor spaces where children can play safely.

In Lincoln Park, visitors can enjoy proximity to the Lincoln Park Zoo and the scenic waterfront, while Lakeview features easy access to the beaches along Lake Michigan. Additionally, some rentals may include amenities such as game rooms, private backyards, and laundry facilities, ensuring a comfortable and enjoyable stay for families.
Can I rent a vacation home with a pool or hot tub in Chicago?
In Chicago, there are plenty of vacation homes available for rent that feature pools and hot tubs, with around 617 options to choose from. Travelers can find properties scattered throughout various neighborhoods, including the trendy Wicker Park and the family-friendly Lincoln Park, both of which offer a mix of urban convenience and local charm.

Many of these rentals come equipped with amenities like private pools, inviting hot tubs, and spacious outdoor areas great for relaxation or entertaining. Inside, guests can typically expect fully equipped kitchens, comfortable living spaces, and modern conveniences such as Wi-Fi and air conditioning.
Can I find long-stay vacation rentals in Chicago?
A long-stay vacation rental in Chicago is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Chicago?
In Chicago, there is a vast selection of pet-friendly house rentals available, with approximately 1,972 options for travelers to consider. Many of these rentals are located in popular neighborhoods such as Lincoln Park and the West Loop, offering a variety of amenities to cater to both humans and their furry companions.

In Lincoln Park, visitors will find homes that come equipped with modern kitchens, spacious living areas, and outdoor spaces, great for pets to enjoy. The neighborhood's namesake park features walking trails and gardens, providing an excellent environment for pet owners to explore with their dogs.

Similarly, the West Loop is known for its vibrant setting and offers vacation rentals that often include rooftop decks and fitness centers. This area is conveniently located near Grant Park, which boasts expansive lawns and walking paths, making it an ideal spot for those looking to enjoy the outdoors with their pets.

Additionally, neighborhoods with a more suburban feel, such as Forest Park, feature larger homes with private yards, ideal for pets to roam. See all pet-friendly rentals in Chicago.
Are there any remote work vacation rentals in Chicago?
In Chicago, there are plenty of remote work vacation rentals available, with approximately 2,826 options to choose from. The city offers a vibrant setting with diverse neighborhoods like Lincoln Park, Wicker Park, and the Loop, each providing great experiences and easy access to local attractions. Many of these properties feature essential remote work amenities such as free Wi-Fi, dedicated desks, and comfortable living spaces designed for productivity.

Travelers can expect modern furnishings, fully equipped kitchens for meal preparation, and some rentals may even offer outdoor spaces or communal areas for relaxation during breaks. With proximity to coffee shops, coworking spaces, and parks, Chicago is an excellent choice for those looking to blend work and leisure in a dynamic urban environment. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Chicago vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Chicago with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Chicago?
In Chicago, popular vacation rental amenities include well-equipped kitchens, allowing guests to prepare their own meals and enjoy a home-cooked experience. Many rentals also feature coffee and tea makers, great for those who appreciate a morning brew. For pet owners, a significant number of properties permit pets, making it easy to travel with furry companions. Additionally, service animals are welcome in many accommodations. Onsite parking is another sought-after amenity, providing convenience for travelers with vehicles.
How early should I book a Chicago vacation rental?
Book your Chicago vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Chicago, Illinois, United States of America?
In Chicago, visitors can explore a diverse array of attractions throughout its vibrant neighborhoods. The Loop is the city's bustling downtown area, where iconic sites such as Millennium Park—home to the famous Cloud Gate sculpture—and the Art Institute of Chicago can be found. This area features numerous vacation rentals with easy access to public transportation, dining, and shopping options.

In the River North neighborhood, art lovers can enjoy a plethora of galleries and the vibrant nightlife scene, while being close to the Magnificent Mile, a premier shopping destination.

For a taste of local culture, Wicker Park offers a hip atmosphere with unique boutiques, music venues, and parks, making it a popular spot for younger travelers. The nearby Ukrainian Village is rich in history and features charming architecture, along with traditional eateries and cultural festivals.

The Lincoln Park area is great for nature enthusiasts, featuring the expansive Lincoln Park Zoo and beautiful gardens. It also has a mix of historic homes and modern vacation rentals, providing a family-friendly environment.
Can I change or cancel my Chicago home rental booking on Vrbo?
To find Chicago vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Chicago vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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