Chicago vacation rentals

We found 4,660 vacation rentals — enter your dates for availability

Discover a selection of 1520 homes, 2704 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:Nov 14 - Nov 21

Image gallery for HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony

Interior
9.2 out of 10 rating
Wonderful
(50 reviews)

HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony

Chicago, IL

18% off
Price is CA $249
CA $2,564 total
includes taxes & fees
HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony

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Find out more about Chicago

Find out more about Chicago

Why visit Chicago

  1. Cultural richness: Discover Chicago's vibrant arts scene, including world-class museums, galleries, and live performances.
  2. Iconic landmarks: Explore famous sites like the Willis Tower, Millennium Park, and Navy Pier.
  3. Outdoor activities: Enjoy the city's beautiful parks, beaches, and waterfront views along Lake Michigan.
  4. Diverse neighbourhoods: Experience the unique charm of Chicago's various neighbourhoods, each offering distinct food and culture.
  5. 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.

  1. 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.
  2. 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.
  3. 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 iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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 CloudyAverageSlightly 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 CloudyModerately LowAverage

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)
  • The Dome at the Parkway Bank Sports Complex (14.4 mi / 23.2 km)
  • Oak Brook Golf Course (15.7 mi / 25.3 km)
  • The Glen Club (17.7 mi / 28.5 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?
When considering a vacation rental in Chicago, one of the most vibrant areas to stay in is the Loop. This central business district is not only the heart of the city but also home to iconic attractions like Millennium Park, where you can marvel at the famous Cloud Gate sculpture, affectionately known as "The Bean." The Loop is also close to the Art Institute of Chicago, renowned for its extensive collection of Impressionist and Post-Impressionist masterpieces. With a wealth of properties available, from chic apartments to luxurious lofts, the Loop provides a superb blend of convenience and cultural experiences.

Another excellent choice is Lincoln Park, which offers a more relaxed, residential feel while still being close to the action. This area is famous for its namesake park, which boasts beautiful gardens, the Lincoln Park Zoo, and stunning views of Lake Michigan. Additionally, Lincoln Park is dotted with charming boutiques, restaurants, and cafés, making it an ideal spot for those looking to immerse themselves in local life. With a variety of vacation rentals ranging from cosy flats to spacious homes, Lincoln Park caters to diverse preferences.

For a more trendy and youthful atmosphere, consider staying in Wicker Park. Known for its vibrant vibe, this neighbourhood features an array of independent shops, art galleries, and vibrant nightlife. Wicker Park is also home to the picturesque Wicker Park itself, superb for picnics or leisurely strolls. The area has a rich selection of vacation rentals, often reflecting the artistic spirit of the neighbourhood, making it a wonderful option for visitors wanting to experience Chicago's creative side.
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 travelling 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.
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 areas along Lake Michigan offer some fantastic options. The neighbourhood of Lincoln Park is particularly appealing, as it provides easy access to the picturesque Lincoln Park Beach, where visitors can enjoy a sandy shoreline and lovely views of the skyline. Many properties in this area are modern and well-equipped, featuring amenities such as spacious decks, outdoor grills, and open-plan living spaces, great for entertaining.

Further along the lakefront, the South Shore neighbourhood is another excellent choice, known for its beautiful beaches and parks. Here, travellers can find charming beachfront cottages or larger houses that often come with private gardens, direct beach access, and family-friendly amenities like games rooms and fully equipped kitchens.

Additionally, the vibrant area of Wicker Park, although slightly further from the immediate beach, offers a lively atmosphere with proximity to both the water and local attractions. Rentals here may include trendy apartments in converted buildings, complete with rooftop terraces that provide stunning views of the lake and city, plus modern conveniences like Wi-Fi and air conditioning.
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 2,295 available throughout the city. These rentals are predominantly located in lively neighbourhoods such as the Loop, River North, and Lincoln Park, close to iconic landmarks like Millennium Park, the Art Institute of Chicago, and the Magnificent Mile. Most apartments feature modern amenities, including fully equipped kitchens, spacious living areas, and some offer stunning views of the city skyline.
Are there any family house rentals in Chicago?
In Chicago, there are numerous family-friendly house rentals available—approximately 2,114 in total throughout the city. Neighbourhoods such as Lincoln Park and Hyde Park are particularly appealing for families, offering spacious homes close to parks and local attractions. In Lincoln Park, visitors can enjoy properties that often feature large living areas, fully equipped kitchens, and outdoor spaces superb for family gatherings, all while being near the Lincoln Park Zoo and the picturesque lakefront.

Hyde Park, known for its cultural offerings, boasts roomy residences that may include amenities like game rooms or backyards for children to play in. This area is also close to the Museum of Science and Industry, making it an educational and fun destination 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 approximately 703 options to choose from. The city is known for its diverse neighbourhoods, such as the vibrant River North area, which offers a mix of modern amenities and cultural attractions, as well as the family-friendly Lincoln Park, where visitors can enjoy parks and the nearby zoo.
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. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Chicago?
In Chicago, there are numerous pet-friendly house rentals available, particularly across various vibrant neighbourhoods. In areas like Lincoln Park, visitors can find well-appointed homes featuring modern kitchens, spacious living areas, and often outdoor spaces ideal for pets. The proximity to Lincoln Park itself, which offers extensive walking trails and gardens, is a significant advantage for travellers with furry companions.

In the West Loop, vacation rentals tend to have contemporary amenities such as rooftop decks and fitness centres, with easy access to nearby parks like Grant Park. This expansive green space not only provides a great area for walks but also hosts various cultural institutions, making it an enjoyable environment for both pets and their owners.
Are there any remote work vacation rentals in Chicago?
In Chicago, there is an impressive selection of remote work vacation rentals, with around 3,140 options available throughout the city. Many of these properties are situated in vibrant neighbourhoods such as the Loop, River North, and Lincoln Park, offering both convenience and a lively atmosphere. Travellers can expect amenities tailored for remote work, including dedicated desk spaces, high-speed Wi-Fi, and ergonomic office furniture. Some rentals may even feature additional perks like laptop workstations and conference rooms, great for those needing a more professional setting. 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 travellers 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 rental amenities typically include fully equipped kitchens, which are ideal for those who prefer to cook during their stay. Most vacation rentals feature essential appliances such as microwaves, stovetops, and refrigerators, along with cookware, dishware, and utensils to facilitate meal preparation. This is particularly advantageous for families or groups who appreciate the convenience of dining in.
When is the best time to visit Chicago for a vacation rental?
The best time to book a vacation rental in Chicago is during the peak season from May to July. This vibrant period draws travellers from around the world, eager to experience the city's lively atmosphere, numerous festivals, and outdoor events. In July, you'll find the city bustling with energy, as residents and visitors alike take advantage of warm temperatures, typically hovering in the mid-20s Celsius, great for exploring Chicago's famous parks, waterfronts, and cultural attractions.

During the summer months, Chicago comes alive with an abundance of activities. From the iconic Taste of Chicago food festival to outdoor concerts and the spectacular fireworks at Navy Pier, there's something for everyone. The city's renowned museums, such as the Art Institute of Chicago and the Field Museum, are also must-visit spots that can be enjoyed in the pleasant weather.

If you're looking for a more budget-friendly option, consider visiting in December. While temperatures drop to around 0 degrees Celsius, the city transforms into a winter wonderland, adorned with festive lights and vacation decorations. This month offers a unique charm, with opportunities to enjoy ice skating in Millennium Park and sipping hot chocolate at the Christkindlmarket.
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?
In Chicago, visitors can explore a range of attractions scattered across various neighbourhoods. The Millennium Park area features the iconic Cloud Gate sculpture, often referred to as "The Bean," and offers a beautiful setting for art and culture enthusiasts. Nearby, the Art Institute of Chicago houses an extensive collection of artworks, making it a must-visit for art lovers.

In the Loop, tourists can marvel at the stunning architecture that defines the city's skyline, with highlights such as the Willis Tower and the Chicago Riverwalk, which is great for leisurely strolls along the water.

Heading towards Lincoln Park, the Lincoln Park Zoo offers a free and family-friendly experience, alongside the picturesque Lincoln Park itself, which is ideal for outdoor activities.

For those interested in a vibrant nightlife scene, the West Loop boasts trendy restaurants and bars, all within close proximity to attractions such as the Chicago Union Station.
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 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 travellers 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 cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
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.

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