West Town vacation rentals

We found 1,428 vacation rentals — enter your dates for availability

Discover a selection of 56 homes, 174 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:Dec 19 - Dec 26
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Find out more about West Town

Find out more about West Town

Why visit West Town

  • Eclectic Neighborhoods: Discover the unique charm of West Town's diverse neighborhoods, filled with friendly locals and a welcoming atmosphere.
  • Cultural Experiences: Engage in the rich culture of the area, with historic buildings, art galleries, and local events.
  • Family-Friendly Activities: Enjoy outdoor adventures and attractions suitable for all ages, making it perfect for family getaways.
  • Vibrant Nightlife: Experience the lively nightlife with trendy bars, music venues, and local entertainment options.
  • Variety of Accommodations: Choose from cozy apartments to spacious vacation homes, ensuring a comfortable stay.

Popular types of accommodation around West Town

If you're exploring vacation rentals in West Town, you're in for a treat. Our most popular accommodations include cozy apartments, spacious houses, and modern condos. Whether you're searching for West Town rentals, West Vancouver apartments, or rooms for rent, we have a variety of options to suit your needs. Rest assured, you'll find the perfect spot to relax and enjoy your stay in this vibrant community.

  • Apartments: The top choice for vacation rentals in West Town, offering a comfortable and convenient stay for individuals or small groups.
  • Houses: A popular option for those seeking a home-like atmosphere, ideal for families or friends vacationing together.
  • Condos: A stylish and modern accommodation type, perfect for visitors wanting a blend of amenities and local charm.
  • Cottages: These quaint retreats provide a cozy environment, ideal for a peaceful getaway.
  • Villas: Spacious and luxurious options, perfect for those looking to indulge during their stay.**

Top attractions near West Town

West Town, Chicago is perfect for family getaways and outdoor adventures. With attractions like skyscrapers, historic buildings, and vibrant streets, there's something for everyone. Explore the area's rich culture and enjoy family-friendly experiences. Don't miss out on the lively nightlife and consider requesting local tours to get the most out of your visit. Whether you're travelling solo or with loved ones, West Town offers a memorable urban experience.

  • Michigan Avenue: A bustling thoroughfare known for its vibrant city atmosphere, Michigan Avenue is lined with high-end shops, restaurants, and cultural landmarks. It's perfect for shopping and enjoying the urban experience.
  • Chicago Riverwalk: This scenic waterfront promenade is ideal for families, offering outdoor activities and picturesque views of the Chicago River. Enjoy leisurely strolls, dining, and various water-related activities.
  • Willis Tower: One of the tallest skyscrapers in the Western Hemisphere, Willis Tower boasts stunning city views from its observation deck, providing a thrilling urban experience above the bustling streets.

Things to do recommended for couples

Looking for a romantic getaway in West Town, Chicago? Enjoy live music at the House of Blues, savour a meal at the historic Michael Jordan Restaurant, or dance the night away at the Aragon Ballroom. Each venue offers a unique atmosphere perfect for couples.

Things to do recommended for families

Families will have a blast at Wrigley Field, only 4.8km away, immersing in the thrilling sports atmosphere. For some relaxation, head to Northerly Island Natural Area, 8.0km away, or enjoy the serene Norridge Park District, located 14.5km from West Town.

Things to do recommended for groups

Experience the vibrant culture of Chicago by catching a show at the Cadillac Palace Theatre, indulging in some retail therapy at the 900 North Michigan Shops, or enjoying games and drinks at Dave & Buster's. These activities are perfect for creating lasting memories with your group.

*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 planning your trip—whether you're traveling with friends, family, pets, or seeking extended stays—it's important to prioritize your preferences when filtering your options. Here are some helpful Vrbo booking tips to guide you.

  • Traveling to West Town with a group: Think about how many bedrooms you'll require, as well as amenities like a complete kitchen or outdoor areas for group gatherings. Luckily, you can easily refine your search for all of these options, and more, on Vrbo.
  • Traveling to West Town with young kids: Traveling with little ones can be quite demanding. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, thinking about your closeness to family-friendly attractions is a wise choice.
  • Taking your pets with you to West Town: For many families, a vacation wouldn’t feel complete without their furry companion by their side. If this resonates with you, consider exploring Vrbo properties that welcome pets. Most 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 West Town: If you’re seeking vacation rentals with special offers 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 accommodations. Don’t forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near West Town

West Town in Chicago offers a vibrant mix of urban charm and scenic beauty, perfect for families and outdoor enthusiasts. Explore the eclectic neighborhoods nearby, where friendly locals and a welcoming atmosphere enhance your experience. Discover desirable spots that showcase the essence of city life and enjoy the unique vibes of this captivating area. With its blend of culture and community, West Town is an ideal destination for an unforgettable vacation.

  • Chicago: Chicago is a vibrant metropolis that offers a rich blend of culture, entertainment, and family-friendly activities. As the home of West Town, the city boasts a variety of attractions, including bustling shopping areas and renowned sports venues. Visitors can explore iconic landmarks such as stadiums and tourist precincts while enjoying diverse culinary options. Chicago’s urban parks provide ample opportunities for outdoor recreation, making it an ideal destination for those seeking an exciting city-themed experience.
  • Downtown Chicago: Located approximately 4.8km from West Town, Downtown Chicago is the heart of the city, filled with towering skyscrapers and cultural landmarks. This dynamic neighbourhood caters to families and outdoor enthusiasts alike, with numerous shopping districts and world-class theatres. Visitors can catch a game at a local stadium or enjoy performances at various entertainment venues. The vibrant atmosphere and rich architectural heritage make Downtown Chicago a must-visit for anyone looking to experience the city's urban charm.
  • East Village: Just 322m from West Town, East Village is a quaint neighbourhood that offers a unique blend of community spirit and urban convenience. This area is perfect for families and those looking for recreational activities, featuring scenic parks and entertainment facilities. Visitors can unwind in local urban parks or enjoy performances at theatres. With its close proximity to West Town, East Village provides a delightful escape with easy access to the bustling energy of Chicago.

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 simple

Are you hoping to save on your upcoming adventure? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, consider booking a longer stay, as this can lead to substantial savings. To discover a Vrbo property that suits your budget, make use of our filters to sort by price, location, and the type of vacation rental that meets your needs.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a user-friendly space for you to plan new adventures, continue from where you last paused, or manage your travel arrangements. You can easily find the properties you’ve saved or booked, organized into sections for Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental accommodation in West Town?
Based on our data, apartments are the most popular vacation rental type in West Town. But as you know, everyone's idea of the perfect stay isn't going to be the same. Vrbo has vacation rentals of all sizes and shapes, and we'll help you locate the perfect fit for you.
How much does it cost to rent a vacation rental in West Town?
The average price for a vacation rental in West Town is based on a number of factors, such as length of stay, season and property type. Whether you'd like a sprawling villa with space for extended family or a cozy cabin just for the two of you, just add your travel dates to see stays with great value.
How much does it cost to rent a beach house in West Town?
The average price for a vacation home close to the beach in West Town depends on when you're going and the type and size of property you're searching for. Find prices easily on Vrbo by entering your travel dates and destination. Then use our filters to pick the number of bedrooms and amenities important to you, like a pool, WiFi and air conditioning.
Are there pet-friendly vacation rentals in West Town?
Good news. There are. You'll have your pick of 146 vacation homes that roll out the welcome mat in West Town on Vrbo. Our furry companions deserve a break too, so simply use our search function for pet-friendly vacation rentals to book a place where Rover can join the fun.
Can I rent a house with a pool in West Town?
Add a whole new level of fun to your adventure by booking your group into one of the five houses with a private pool in West Town. Use our search filter to find the kind of property you want on Vrbo, and then spend your downtime playing and splashing in a swimming pool that's exclusively for you.
What are popular rental amenities in West Town?
A nearby river, a nearby waterfront and a firepit rank as the most popular rental amenities in West Town. Whether you're planning to travel by yourself, with your other half or a group of family members, Vrbo will help you find a vacation rental that suits your tastes with all the features you're looking for.
Are there large group vacation rentals in West Town?
West Town has 15 vacation properties that can fit 10 or more guests. These stays come with the space and privacy you need to enjoy good times with loved ones.
Are there vacation rentals in West Town that welcome kids?
With 139 family-friendly vacation properties to choose from in West Town, now is a fantastic time to introduce your little ones to the wonders of travel. Check our "Properties good for families" filter to look for stays packed with conveniences perfect for families on the move, like extra bedrooms, outdoor spaces, entertainment areas and bunk beds.
What are the top attractions for families in West Town?
There are plenty of amazing things to see and do with the family in West Town, including:

  • Navy Pier
  • Chicago Riverwalk
  • Shedd Aquarium

Are there one-bedroom vacation rentals in West Town?
Yes, West Town has 30 one-bedroom rentals on offer. Often positioned in sought-after areas because of their compact size, a one-bedroom vacation property is great if you're getting away with your partner or a friend. And with plenty of home comforts like laundry facilities and more privacy than a standard hotel, you'll be able to relax while enjoying this amazing destination.
Can I find two-bedroom vacation rentals in West Town?
West Town has 38 two-bedroom vacation properties to choose from. Go for a vacation home with all the space and privacy you're looking for at a price you'll love on Vrbo.
Are there vacation rentals with WiFi in West Town?
West Town has 62 vacation rentals with WiFi, so you'll be able to stay connected while you're away. Simply check the "WiFi" box in our handy search filter to find the perfect property. From streaming movie blockbusters to catching up on social media, these Vrbo homes will keep you online.
How can I find vacation rentals with air conditioning in West Town?
You'll find 129 Vrbo vacation rentals with air conditioning in West Town providing that cooling breeze and extra bit of comfort. Enter your preferred travel dates and then use our handy filters to locate properties with air conditioning.
How old do you have to be to rent a vacation rental in West Town?
The minimum age is normally 16, 18 or 21. It can change from one property to another on Vrbo, so check the rules of your chosen West Town vacation home before booking your stay.
How long can I rent a vacation rental in West Town for?
It's up to the West Town property. To browse available options offering extended stays, just enter your travel dates and guest number into the Vrbo search page. You can enjoy having the whole property to yourself, as well as amenities such as air conditioning, a fully-equipped kitchen and outdoor spaces where the kids can burn off energy. Keep your eyes peeled for any long-term stays that offer weekly or monthly discounts.

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