West Town vacation rentals

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Discover a selection of 53 homes, 195 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.

Vacation rentals with weekly discounts - West Town

Showing deals for:Aug 14 - Aug 21

Image gallery for Luxury 6BD/5BTH + Roofdeck - Downtown Chicago!

Living area
9.2 out of 10, Wonderful, (10 reviews)
Wonderful
(10 reviews)

Luxury 6BD/5BTH + Roofdeck - Downtown Chicago!

Chicago

9% off
Price is $1,530
$10,712 for 7 nights
All fees included
Luxury 6BD/5BTH + Roofdeck - Downtown Chicago!

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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.

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 around 136 available across this vibrant neighborhood known for its lively mix of culture and dining. These apartments typically come with fully equipped kitchens, comfortable living areas, and often feature amenities like in-unit laundry and balconies for enjoying the lively surroundings.

For those needing more space, there are approximately 43 vacation houses that cater to families or groups, offering multiple bedrooms, private outdoor spaces, and sometimes even BBQ facilities for gatherings. Additionally, about 22 condos can be found, which often include shared amenities such as pools and fitness centers.
Are there any beach house rentals in West Town?
In West Town, there are about 17 beach house rentals available, primarily situated in vibrant neighborhoods that offer easy access to local attractions and the city's cultural scene. These vacation homes typically feature amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces for relaxation. Guests can expect a comfortable, home-like environment that is ideal for families or groups looking to enjoy a unique stay in the heart of Chicago.
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, popular rental amenities include fully equipped kitchens, allowing travelers to prepare their own meals with ease. Many rentals also feature coffee and tea makers for those who enjoy a warm beverage in the morning. Onsite parking is commonly available, providing convenience for guests with vehicles. Additionally, many properties come with decks or patios, offering outdoor space to relax and enjoy the neighborhood's ambiance. For pet lovers, a number of rentals are pet-friendly, accommodating furry companions during their stay.
Can I find family house rentals in West Town?
In West Town, Illinois, there is a wide selection of family-friendly house rentals available, with approximately 88 options to choose from. This vibrant neighborhood is known for its lively mix of culture, dining, and entertainment, making it an ideal location for families.

Many of these homes offer spacious layouts with multiple bedrooms, allowing for comfortable accommodations for larger groups. Visitors can expect amenities such as fully equipped kitchens, cozy living rooms, and outdoor spaces for relaxation or play. Some properties may even have features like game rooms or private patios, great for enjoying time with family after a day of exploring.

The area is also conveniently located near various parks, like Humboldt Park, which offers playgrounds, sports facilities, and beautiful walking paths. Additionally, families can enjoy nearby attractions like the trendy shops and restaurants along Milwaukee Avenue.
Can I rent a vacation home with a pool or hot tub in West Town?
In West Town, Illinois, travelers have several options for vacation rentals that feature pools and hot tubs, with around 13 rentals offering pools and 22 providing hot tubs. This vibrant neighborhood in Chicago is known for its vibrant culture and proximity to the city's attractions. Vacation homes here often come equipped with amenities such as private pools for refreshing swims during the warmer months, and hot tubs superb for relaxing after a day of exploring.

Many of these rentals also include spacious living areas, fully equipped kitchens, and outdoor spaces where guests can enjoy barbecues or simply gather to unwind.
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.
Can I book 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. This vibrant neighborhood in Chicago offers a variety of accommodations that often come with modern amenities such as fully equipped kitchens, spacious living areas, and sometimes outdoor spaces like balconies or patios, great for enjoying the city's atmosphere.

West Town is known for its artistic vibe and lively dining scene, with many pet-friendly cafes and restaurants nearby, making it convenient for those traveling with pets. Additionally, the area provides access to parks where you can take your dog for a walk or enjoy some outdoor time.
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?
The best time to visit West Town for a vacation rental is during the peak season from March to May, when the city comes alive with vibrant energy and a variety of activities. This period is especially appealing to travelers looking to immerse themselves in the local culture, enjoy outdoor spaces, and partake in lively events as the weather warms up.

March is particularly popular, as visitors can revel in the early signs of spring with temperatures ranging from the low 40s to mid-60s Fahrenheit. This comfortable climate is great for exploring the charming streets filled with unique shops, art galleries, and welcoming cafés. It's also an excellent time for outdoor enthusiasts to take advantage of the city's parks and green spaces, where you can enjoy leisurely strolls or picnics.

If you're looking for a more budget-friendly option, consider visiting in December. While it's the low season, the holiday season offers a different charm with festive decorations and local events. This quieter month allows for a more intimate experience of West Town's winter atmosphere, ideal for those who appreciate a slower pace.

Ultimately, your choice of when to visit West Town will depend on your preference for vibrant spring activities or a cozy winter getaway.
Are there any remote work vacation rentals in West Town?
In West Town, Illinois, there are numerous vacation rentals available for remote work, with around 163 options to choose from. This vibrant neighborhood is known for its eclectic mix of art, dining, and cultural experiences, making it an appealing place for those looking to balance work with leisure. Many of the rentals are equipped with essential remote work amenities, including high-speed Wi-Fi, dedicated workspaces, and comfortable seating, ensuring a productive environment.

Travelers can expect properties featuring modern kitchens for meal prep, cozy living areas for relaxation, and access to local cafes and restaurants that are conducive to remote work. The neighborhood is also well-connected to public transportation, allowing for easy access to downtown Chicago and other attractions. 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, Illinois, United States of America?
In West Town, visitors can discover a range of attractions that capture the neighborhood's energetic charm and vibrant culture. The area is known for its artistic flair, with numerous galleries and studios showcasing local talent, particularly in the Wicker Park section. Here, travelers can explore the iconic Wicker Park itself, which features beautiful green spaces, walking paths, and a charming pond, making it a great spot for relaxation or a picnic.

Nearby, the bustling Division Street offers a variety of boutiques, cafes, and restaurants, reflecting the neighborhood's diverse culinary scene. This area is also home to live music venues and nightlife, great for those looking to experience the local entertainment culture.

For those interested in history and architecture, the historic buildings and converted warehouses in the area provide a glimpse into West Town's past.
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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