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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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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Find out more about Chicago

Why visit Chicago

Cultural richness: Discover Chicago's vibrant arts scene, including world-class museums, galleries, and live performances.
Iconic landmarks: Explore famous sites like the Willis Tower, Millennium Park, and Navy Pier.
Outdoor activities: Enjoy the city's beautiful parks, beaches, and waterfront views along Lake Michigan.
Diverse neighbourhoods: Experience the unique charm of Chicago's various neighbourhoods, each offering distinct food and culture.
Comfortable accommodations: Choose from a range of vacation rentals, stylish condos, and hotels with stunning city views.

Popular types of accommodation in Chicago

Discover the charm of vacation rentals in Chicago and its surrounding areas with our customer-centric platform. Whether you're seeking a chic apartment, a cozy private vacation home, or a stylish condo, we have options to suit your needs. Enjoy the convenience of hotel rentals, select hotels, and even accommodations with balconies for stunning city views. Let us help you find the perfect getaway in the Windy City!

Apartments: The top choice for visitors in Chicago, these self-contained units offer the comforts of home in vibrant city settings.
Houses: Ideal for families or groups, these spacious homes provide privacy and a home-like atmosphere.
Condos: A popular option, condos combine modern amenities with communal facilities for a well-rounded stay.
Cottages: These quaint accommodations offer a charming and cozy retreat, perfect for a relaxing getaway.
Villas: Luxurious and spacious, villas provide a lavish experience for those seeking elegance and comfort.**

Top attractions in Chicago

Chicago and its surroundings offer a fantastic blend of family-friendly activities, outdoor adventures, and vibrant city experiences. Explore urban parks, modern colleges, and beautiful beaches while soaking in the rich culture of the area. Don't miss the chance for sightseeing in Chicago, ensuring you create lasting memories during your visit to this iconic city.

McCormick Place: As one of the largest convention centres in North America, McCormick Place offers a dynamic atmosphere for events and conferences, showcasing cutting-edge architecture and business energy. It's a hub for networking and innovation.
Navy Pier: This lively jetty features stunning waterfront views, an array of entertainment, public art installations, and a friendly atmosphere. Enjoy recreational activities, dining, and cultural experiences all in one vibrant spot.
Michigan Avenue: Known as the Magnificent Mile, this bustling street is lined with high-end shops, iconic architecture, and vibrant city life. It's an essential destination for shopping and exploring Chicago's urban charm.

Things to do recommended for couples

Looking for a romantic getaway in Chicago? Enjoy a medieval feast at Schaumburg Medieval Times, experience live music at the Aragon Ballroom, or indulge in luxury at Chevy Chase Country Club. Each spot offers a unique vibe perfect for couples seeking memorable moments together.

Things to do recommended for families

Families visiting Chicago can catch a game at Wrigley Field for an exciting sports experience, splash around at the Great Wolf Lodge Water Park for adventure and entertainment, or unwind in the tranquil Northerly Island Natural Area, perfect for wellness and relaxation.

Things to do recommended for groups

Your group can enjoy a captivating show at the Chicago Theatre, indulge in shopping at Woodfield Mall, and unleash creativity at the LEGOLAND® Discovery Center. Each experience offers a vibrant mix of culture, entertainment, and family-friendly fun, perfect for creating lasting memories in the Windy City.

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

When planning your trip, whether you're travelling with a group, family, pets, or seeking extended stays, it's important to prioritize your needs. Here are some helpful Vrbo booking tips to assist you.

Traveling to Chicago with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for these options and many more on Vrbo.
Traveling to Chicago with young kids: Traveling with young children can present its own set of challenges. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it’s wise to take into account your closeness 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 you can relate, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
Planning for a long term stay visiting Chicago: If you're in search of vacation rentals that offer special rates 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 rental options. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in Chicago

Chicago and its surrounding areas offer a vibrant mix of urban charm and artistic flair, making it an ideal destination for family-friendly vacations. Explore the city's famous landmarks, discover hidden gems in its diverse neighbourhoods, and enjoy the distinct seasons that enhance your travel experience. With friendly locals and a rich cultural scene, you'll find plenty of opportunities for adventure and relaxation in this bustling metropolis.

Chicago: Chicago, a vibrant city situated on the southwestern shore of Lake Michigan, is known for its rich history and diverse culture. The city is a hub for family-friendly activities, outdoor adventures, and urban experiences. Visitors can explore iconic landmarks like the Willis Tower and Millennium Park, while the bustling shopping districts and renowned theatres provide ample entertainment. Sports enthusiasts can cheer on their favourite teams at famous stadiums, and the city's tourist precinct offers a variety of attractions for all ages, making Chicago a must-visit destination.
Downtown Chicago: Downtown Chicago, the heart of the city, offers an electrifying atmosphere filled with energy and excitement. This neighbourhood is perfect for families and those seeking an outdoor city experience. Stroll along the picturesque Riverwalk, enjoy the art installations at Millennium Park, or indulge in shopping at renowned stores. The area is also home to impressive theatres and arena entertainment facilities, ensuring that visitors have a wealth of options for leisure and relaxation. With proximity to major landmarks like the Art Institute and various sports facilities, Downtown Chicago is a dynamic locale to explore.
Schaumburg: Schaumburg is a thriving city located to the northwest of Chicago, known for its family-oriented atmosphere and business-friendly environment. The city boasts an impressive shopping centre, Woodfield Mall, which is one of the largest in the United States, offering a plethora of retail options. In addition to shopping, visitors can enjoy various theatres and event venues that frequently host conferences and conventions. With its blend of urban amenities and suburban charm, Schaumburg provides a unique experience for both leisure and business travellers while still being a short drive from Chicago.

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 December to February 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	Slightly Low
April	46.0°F (7.8°C)	Light Rain	Mostly Sunny	Average	Average
May	57.0°F (13.9°C)	Light Rain	Mostly Sunny	Average	Average
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	Slightly High
August	73.0°F (22.8°C)	Light Rain	Mostly Sunny	Moderately High	Slightly High
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	Average
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 adventure? Consider being flexible with your travel dates, as prices can fluctuate. Plus, booking an extended stay can result in significant savings. To discover the ideal Vrbo property that fits your budget, use our filters to refine your search by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a user-friendly area for you to plan new adventures, resume your previous arrangements, or manage your travel itinerary. You can easily access your saved or booked properties organized into categories such as Potential, Upcoming, or Current Trips. To begin utilising Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Travel to exciting Chicago

Take a vacation to Chicago and enjoy the area's theater scene, architecture and museums. This city is cosmopolitan and scenic, recognized for its art, monuments and entertainment. Michigan Avenue and Navy Pier are a couple of places to search for that perfect souvenir. Whether you're planning a family holiday, romantic stay or friends trip, vacation rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in Chicago

Are you hoping to find things to do during your stay? Venture out of your vacation home and check out everything that Chicago has to offer. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

Dave & Buster's (1.4 mi / 2.3 km)
Lincoln Park Zoo (2.8 mi / 4.5 km)
Galloping Ghost (12.5 mi / 20.1 km)
Harborside International Golf Center (13 mi / 21 km)
Adagio Teas (14.1 mi / 22.6 km)
The Dome at the Parkway Bank Sports Complex (14.4 mi / 23.2 km)

Exploring the natural features in Chicago

Whether you're an active traveler or just want to spend some time taking in the scenery, Chicago is a great place to get outside. Here are some of the area’s most eye-catching natural features, all within 30 miles (48.2 km) of the city center:

Millennium Park (0.3 mi / 0.5 km)
Grant Park (0.7 mi / 1 km)
Maggie Daley Park (0.5 mi / 0.8 km)
Ohio Street Beach (1.2 mi / 1.9 km)
Burnham Park (1.4 mi / 2.2 km)
Oak Street Beach (1.6 mi / 2.5 km)

Transportation options to and around Chicago

Fly into Chicago Midway Airport (MDW), the closest airport, located 8.6 mi (13.9 km) from the city center. If you can't find a flight that works for your travel itinerary, you could book a flight to Chicago O'Hare Intl. Airport (ORD), which is 15.7 mi (25.3 km) away.

If you're traveling by train, Millennium Station, Chicago Van Buren Street Station and Chicago Union Station are the main stations that serve the city. You can get around Chicago by jumping on the metro at Monroe Station (Red Line), Monroe Station (Blue Line) or Adams-Wabash Station.

Frequently asked questions

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

Among the most sought-after neighborhoods to enjoy a vacation rental in Chicago is Near North Side. When you stay here, you’ll be near top attractions like Navy Pier and Chicago Childrens Museum.

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

The most desirable types of vacation rentals in Chicago are apartments. After something a little different? Vrbo has plenty of options to match our guests’ diverse needs, so you’ll see vacation properties in all shapes and sizes. The perfect home away from home is waiting for you — get yours today.

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

The average price for a vacation home in Chicago can vary based on factors like property type, length of stay and time of year. Whether you’re thinking about a sprawling villa with a pool or a quaint cabin ideal for just you and the kids, just enter your dates of travel to see stays that offer great value.

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

The average price for a vacation home by the beach in Chicago depends on when you’re going and the type and size of property you’re searching for. You can find prices easily and quickly on Vrbo by entering your dates of travel. Then use the filters to select the number of bedrooms and amenities important to you, such as a pool, air conditioning and WiFi.

Are there pet-friendly vacation rentals in Chicago?

With 2,074 properties that allow pets, your furry buddy can join in the fun on your Chicago getaway. Use our filter tool to search our pet-friendly vacation rentals and find a stay that’ll set tails wagging on Vrbo.

Can I rent a house with a pool in Chicago?

Add a whole other level of fun to your getaway by booking one of the 392 houses with a private pool in Chicago. Use our search filter to find properties with pools on Vrbo, then spend your days splish-splashing around in a swimming pool that’s just for you.

What are popular rental amenities in Chicago?

A firepit, nearby museums and a barbecue grill head the list of most popular rental amenities in Chicago. Whether you plan to travel solo, with a partner or a bunch of friends, Vrbo will help you find a vacation home that suits your style with a load of extras you’ll love.

Are there large group vacation rentals in Chicago?

Take your pick of 185 vacation properties in Chicago that can host 10 or more people. Whether you’re planning a vacation with extended family or an event like a birthday party, there’s enough space to get your group together under the same roof.

Are there vacation rentals in Chicago that welcome kids?

With 2,058 family-friendly vacation rentals to select from in Chicago, there’s never been a better time to introduce your little ones to the magic of travel. Just check our “Properties good for families” filter box to look for stays loaded with amenities perfect for vacationing families, such as kitchens, outdoor spaces, entertainment areas and hot tubs.

What are the top attractions for families in Chicago?

Keep your kids busy at these fabulous family-friendly attractions in Chicago:

Navy Pier
Chicago Riverwalk
Shedd Aquarium

Are there one-bedroom vacation rentals in Chicago?

Yes, you can pick from 670 one-bedroom rentals in Chicago. Whether you’d like a comfy cottage or a cabin, our one-bedroom properties are perfect if you don’t require tons of space. One of the best parts about having your own digs? You’ll never need to share your adventure with strangers.

Can I find two-bedroom vacation rentals in Chicago?

You can select from 568 two-bedroom vacation homes in Chicago. Give the kids the second room or fill it with a couple of your best buddies. There’s ample space for whoever’s lucky enough to be joining your adventure.

Are there vacation rentals with WiFi in Chicago?

Chicago has 685 vacation rentals with WiFi, so you’ll be able to stay connected when you’re away. Simply check the “WiFi” box in our handy search filter for a list of properties with this feature. From streaming movies with the family to posting pics on social media, these Vrbo homes make it easy to get online.

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

Chicago has 1,970 vacation rentals where you’ll be able to relax in air-conditioned comfort. To find a stay on Vrbo featuring this amenity, choose your travel dates and use the convenient filters to select the “air conditioning” box.

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

You should check with the Chicago vacation home you’re considering on Vrbo as the age limit differs. However, it’s typically 16, 18 or 21.

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

The length of time you can rent a vacation rental in Chicago differs according to the property. Simply enter your preferred travel dates to view a list of options offering extended stays. With tons of features such as air conditioning and kitchens, as well as some offering weekly or monthly discounted prices, you’re sure to discover a perfect place to call your home away from home in Chicago.