West Town vacation rentals

We found 1,506 vacation rentals — enter your dates for availability

Discover a selection of 55 homes, 188 apartments, and other vacation rentals in West Town that are perfect for your trip. Whether you're staying in a vacation rental with family or friends, you'll find the best amenities for hanging out with the people that matter most, which might include parking and a fireplace. You'll be sure to find a rental for everyone's needs, including places that are non-smoking or accessible.

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Find out more about West Town

Why visit West Town

  • Eclectic Streets: Discover vibrant streets lined with local cafes and unique shops that showcase the neighborhood's urban charm.
  • Family-Friendly Activities: Enjoy a variety of cultural experiences and outdoor activities perfect for families and travelers alike.
  • Scenic Parks: Venture into nearby parks for relaxing outdoor experiences and welcoming atmospheres.
  • Rich Heritage: Immerse yourself in the area's rich history through its towering skyscrapers and historic buildings.
  • Diverse Accommodations: Choose from cozy apartments, spacious homes, and stylish lofts for a comfortable stay.

Popular types of accommodation around West Town

West Town offers a variety of vacation rentals to suit every traveler’s needs. Whether you're looking for a cozy bedroom apartment, a spacious private vacation home, or a stylish modern loft, you'll find plenty of options. Popular choices include Dallas and DeSoto apartments, as well as Duncanville condos. Explore the best of West Town with accommodations that provide comfort, convenience, and a touch of local charm.

  • Apartments: The top choice for visitors, offering comfortable living spaces with essential amenities for an enjoyable stay in West Town.
  • Houses: Ideal for families or groups, these homes provide a cozy atmosphere and a sense of privacy during your vacation.
  • Condos: A popular option, offering modern facilities and often located in vibrant areas for a lively experience.
  • Cottages: Quaint and charming, these rentals provide a rustic retreat amidst the urban environment of West Town.
  • Villas: Luxurious accommodations that deliver spacious living and upscale amenities for a lavish getaway.**

Top attractions near West Town

West Town, Chicago, is perfect for family-friendly, outdoor, and city-themed vacations. Visitors can explore a variety of attractions, including towering skyscrapers, vibrant streets, and historic buildings. The area offers cultural experiences and activities ideal for families and travelers looking to immerse themselves in the city's rich heritage. Be sure to take advantage of the local points of interest that highlight the unique character of this vibrant neighborhood.

  • Michigan Avenue: Known as the Magnificent Mile, this bustling street features high-end shopping, world-class dining, and vibrant city life. Stroll along its wide sidewalks and enjoy stunning architecture and cultural landmarks.
  • Chicago Riverwalk: A scenic promenade along the Chicago River, perfect for families and outdoor enthusiasts. Enjoy beautiful views, public art, dining options, and recreational activities like kayaking and boat tours.
  • Willis Tower: Once the tallest building in the world, this iconic skyscraper offers breathtaking views from its observation deck, Skydeck. Experience the thrill of standing on the glass balcony extending out over the city.

Things to do recommended for couples

For a romantic getaway in West Town, enjoy live music at the House of Blues Chicago, just 2 miles away. Savor a delightful meal at the Historic Michael Jordan Restaurant, 3 miles from your stay. Don’t miss the vibrant atmosphere at the Aragon Ballroom, 5 miles away.

Things to do recommended for families

During your family visit to West Town, explore Wrigley Field for thrilling sports action, unwind at Northerly Island Natural Area surrounded by nature, or enjoy wellness activities at The East Bank Club. Each destination offers a unique experience for family travelers.

Things to do recommended for groups

Groups visiting West Town can enjoy a captivating show at the Cadillac Palace Theatre, laugh together at the Second City comedy club, and shop at Chicago Place Mall, all within a 2-mile radius, offering vibrant culture, entertainment, and family-friendly experiences.

*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 around West Town

When traveling with a group, family, or pets, or if you're planning an extended stay, it's important to set your priorities when searching. Here are some helpful booking tips for Vrbo to guide you.

  • Traveling to West Town with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor area for group get-togethers. The good news is that you can easily narrow down your options for all of these amenities and more on Vrbo.
  • Traveling to West Town 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'll be to family-friendly attractions.
  • Taking your pets with you to West Town: For many families, a vacation isn’t truly fulfilled without their furry companion by their side. If this resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly properties come equipped with feeding bowls and cozy beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting West Town: If you're in search of vacation rentals with 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 your search criteria as well.

Where to stay near West Town

West Town, Chicago, offers a vibrant mix of urban charm and family-friendly experiences. Explore the neighborhood's eclectic streets filled with local cafes and unique shops. Venture into nearby neighborhoods for scenic parks and welcoming atmospheres, perfect for outdoor activities. Whether you're enjoying the lively vibes of West Town or discovering the beautiful western suburbs, your vacation will be filled with delightful sights and friendly people, making it an ideal destination for all types of travelers.

  • Chicago: As a vibrant metropolis, Chicago is the third-largest city in the United States and the home of West Town. This bustling urban center offers an array of experiences for families, outdoor enthusiasts, and city explorers alike. Visitors can enjoy a diverse shopping scene, catch a game at one of the major sports stadiums, or immerse themselves in cultural education at local museums. Chicago's iconic landmarks, such as the Willis Tower and Millennium Park, provide unforgettable settings for both sightseeing and relaxation.
  • Downtown Chicago: Located approximately 3 miles from West Town, Downtown Chicago is the city's energetic core. This area is a family-friendly destination filled with shopping districts, renowned theaters, and entertainment facilities. Spend an afternoon strolling along the Magnificent Mile or take in a show at one of the many theaters. With attractions like the Art Institute of Chicago and the historic Chicago Riverwalk nearby, Downtown serves as a perfect blend of culture, recreation, and excitement.
  • East Village: Just 0.2 miles from West Town, East Village is a charming neighborhood known for its eclectic vibe and community spirit. This area is perfect for families and outdoor lovers, featuring lush parks and recreational facilities. Visitors can enjoy performances at local theaters or unwind at the urban parks nearby. The neighborhood is also close to sports facilities and stadiums, making it an ideal spot for catching a game or enjoying outdoor activities.

Best time to go to West Town

If you're planning a trip to West Town, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from March to May, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January25.7°F (-3.5°C)Light RainMostly CloudyAverageSlightly Low
February27.0°F (-2.8°C)Light RainMostly CloudyAverageSlightly Low
March37.0°F (2.8°C)Light RainMostly CloudyHighSlightly Low
April46.0°F (7.8°C)Light RainMostly SunnyHighAverage
May57.0°F (13.9°C)Light RainMostly SunnyHighAverage
June67.3°F (19.6°C)Light RainMostly SunnyAverageSlightly High
July73.4°F (23.0°C)Light RainMostly SunnyAverageSlightly High
August73.0°F (22.8°C)Light RainMostly SunnyAverageSlightly High
September67.1°F (19.5°C)Light RainMostly SunnyAverageAverage
October54.9°F (12.7°C)Light RainMostly SunnyLowAverage
November42.3°F (5.7°C)Light RainMostly SunnyLowAverage
December33.1°F (0.6°C)Light RainMostly CloudyLowAverage

Booking with Vrbo is a breeze

Are you hoping to save on your upcoming trip? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, booking a longer stay can lead to considerable savings. To discover a Vrbo property that suits your budget, feel free to use our filters to narrow down your options by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and receive OneKeyCash on the full booking amount. Being the planner truly has its benefits. When you enroll in our travel rewards program, One Key, you'll gain access to exclusive discounts and accumulate OneKeyCash on eligible bookings. Sign up today and begin enjoying your savings.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board offers a user-friendly platform for planning your trips. You can easily create new itineraries, resume previous ones, or organize your travel plans all in one place. You'll see the properties you've saved or booked neatly sorted into sections for Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply head over to: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in West Town?
In West Town, apartments are the most popular vacation rental option, with approximately 114 available throughout the area. These apartments are typically situated in vibrant neighborhoods, offering easy access to local cafes, shops, and cultural venues. Travelers can expect amenities such as fully equipped kitchens, spacious living areas, and often in-unit laundry facilities, providing a comfortable and convenient stay.

For those seeking more space, about 47 vacation houses are also available, featuring multiple bedrooms, private yards, and outdoor seating areas, making them suitable for families or groups. Additionally, there are around 34 condos, which offer a mix of modern amenities and communal facilities, such as pools or fitness centers.
Are there any beach house rentals in West Town?
In West Town, Illinois, there are approximately 50 beach house rentals available, primarily located near the waterfront areas along the Chicago River and close to the vibrant neighborhoods of Wicker Park and Ukrainian Village. Travelers can expect a variety of amenities in these rentals, including spacious layouts, modern kitchens, and outdoor spaces for relaxation. Many properties feature large windows that offer views of the cityscape, while some may even include rooftop decks or balconies for enjoying the urban scenery.
How much does it cost to rent a vacation home in West Town?
Prices for vacation rentals in West Town 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 West Town 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 West Town vacation house rentals?
You can find great discounts on house rentals in West Town 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.
What are popular rental amenities in West Town?
In West Town, travelers can expect popular vacation rental amenities that enhance their stay. Most rentals come with fully equipped kitchens, allowing guests to prepare their own meals, along with a coffee and tea maker for those who enjoy a warm beverage. Many properties feature patios, providing an outdoor space to relax and enjoy the neighborhood ambiance. Onsite parking is also a common amenity, offering convenience for those who may be driving.
Are there any family house rentals in West Town?
In West Town, Illinois, there are some family-friendly house rentals available, with a total of around 116 options to choose from. This vibrant neighborhood is known for its vibrant mix of culture and community, making it an excellent choice for families. Many properties offer spacious living areas, fully equipped kitchens, and backyards or patios where children can play and enjoy the outdoors.

Visitors can explore nearby attractions such as the popular Humboldt Park, which features playgrounds, walking trails, and beautiful gardens. Additionally, the area boasts a variety of family-friendly dining options and local shops, ensuring that you have everything you need within reach.
Can I rent a vacation home with a pool or hot tub in West Town?
In West Town, Illinois, travelers can find several vacation homes available for rent that come with pools, as well as 17 options featuring hot tubs. This vibrant neighborhood offers a mix of urban charm and accessibility to the rest of Chicago. Many of these properties provide desirable amenities, including private pools for relaxation and hot tubs for unwinding after a day of exploring the city. Expect to find spacious living areas, fully equipped kitchens, and outdoor spaces that are superb for gatherings or enjoying warm summer evenings.
Are there any West Town vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in West Town 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.
Are there pet-friendly vacation rentals in West Town?
Yes, you can book pet-friendly vacation rentals in West Town, where there are numerous options available for travelers with pets. This vibrant neighborhood features a variety of accommodations that often include modern amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces like patios or balconies, great for enjoying the city atmosphere.

West Town is known for its lively mix of shops, cafes, and parks, providing ample opportunities for pet owners to explore. Nearby Humboldt Park offers a large green space with walking trails and a dog park, making it an ideal spot for letting your furry friends roam and enjoy the outdoors. Additionally, the area boasts pet-friendly dining options, allowing you to enjoy meals while keeping your pet by your side.
Can I find long-stay vacation rentals in West Town?
A long-stay vacation rental in West Town 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.
When is the best time to visit West Town for a vacation rental?
March is the most popular time to visit West Town, as it marks the beginning of the peak season, which runs from March to May. This vibrant neighborhood in Chicago attracts travelers eager to explore its energetic mix of art, culture, and culinary delights. Spring ushers in milder temperatures, typically ranging from the mid-40s to mid-60s Fahrenheit, creating a friendly space for outdoor activities and leisurely strolls along the picturesque streets.

During these months, you can indulge in a variety of experiences, from visiting local artisan shops to enjoying the flourishing restaurant scene. March, in particular, offers a lively ambiance as the city comes alive with events and activities celebrating the arrival of spring.

For those looking for a more budget-friendly option, consider planning your trip in December. While it's the low season, this month provides a unique charm with festive decorations and holiday events, allowing you to enjoy the city in a more tranquil setting.

Ultimately, your choice of when to visit West Town should align with your preference for bustling energy and lively social scenes in the spring, or a quieter and more reflective experience in the winter months.
Are there any remote work vacation rentals in West Town?
In West Town, Illinois, there are numerous remote work vacation rentals available, with around 149 options to choose from. This vibrant neighborhood is known for its energetic mix of culture, dining, and community activities, making it an appealing spot for those who need to balance work and leisure. Many of these rentals come equipped with essential remote work amenities, including high-speed WiFi, dedicated desks, ergonomic chairs, and comfortable laptop workspaces. Some properties may also feature additional conveniences like computer monitors and safes for securing valuables.

The area is also rich in local attractions, with nearby parks, cafes, and restaurants providing great spots for breaks or after-work relaxation. West Town's unique neighborhoods, such as Wicker Park and Ukrainian Village, are just a short distance away, offering a variety of entertainment and cultural experiences. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a West Town vacation rental?
Book your West Town 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 West Town?
In West Town, visitors can explore a variety of attractions that reflect the neighborhood's vibrant culture and artistic spirit. The area is known for its eclectic mix of dining options, ranging from cozy cafes to trendy restaurants, particularly along Milwaukee Avenue. Visitors can stroll through the historic streets of Wicker Park, which is adjacent to West Town, where they can find unique boutiques, art galleries, and the iconic Wicker Park itself, offering green space and a picturesque setting for relaxation.

For those interested in art and culture, the nearby Ukrainian Village features beautiful churches and cultural institutions that celebrate the area's rich heritage. In addition, the area is home to several music venues and bars that showcase local talent and live performances, contributing to West Town's lively nightlife scene.
Can I change or cancel my West Town home rental booking on Vrbo?
To find West Town 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 West Town 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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