Photo by Audrey Stocker

Bucktown vacation rentals

We found 109 vacation rentals — enter your dates for availability

Discover a selection of 9 homes and other vacation rentals in Bucktown that are perfect for your trip. Whether you're traveling with your kids or with friends, vacation homes have the amenities you need and want for your stay, which might include air conditioning and a pool. What you'll find is a rental for everyone's needs, including options that are accessible or non-smoking.

Vacation rentals with weekly discounts - Bucktown

Showing deals for:Jan 9 - Jan 16

Image gallery for Unique And Amazing Gigantic Sunlit Loft ~ One Of A Kind ~ Excellent Location!

Living Room
9.8 out of 10, Exceptional, (53 reviews)
Exceptional
(53 reviews)

Unique And Amazing Gigantic Sunlit Loft ~ One Of A Kind ~ Excellent Location!

Chicago, IL

9% off
Price is $1,474
$10,316 for 7 nights
All fees included
Unique And Amazing Gigantic Sunlit Loft ~ One Of A Kind ~ Excellent Location!

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Bucktown

Find out more about Bucktown

Why visit Bucktown

  • Vibrant Art Scene: Experience Bucktown's rich artistic culture through galleries and street art.
  • Eclectic Shopping: Discover unique boutiques and vintage shops that showcase local artisans.
  • Delicious Dining: Enjoy a diverse range of dining options, from trendy cafes to family-friendly restaurants.
  • Urban Parks: Relax in beautiful parks that offer outdoor activities and green spaces for families.
  • Family-Friendly Vibes: Bucktown provides a welcoming atmosphere, perfect for creating lasting memories.

Popular types of accommodation around Bucktown

Discover the charm of Bucktown with our selection of vacation rentals. Whether you're seeking stylish apartments, houses, or cozy condos, we have options that cater to every traveler. Bucktown's unique vibe makes it a perfect spot for your getaway. Explore our Bucktown rentals to find the ideal apartment in Chicago that suits your needs and enjoy your stay in this vibrant neighborhood.

  • Apartments: The top choice for travelers in Bucktown, offering modern living spaces with convenient amenities for a comfortable stay.
  • Houses: A fantastic option for groups or families, these homes provide a home-like atmosphere and privacy during your visit.
  • Condos: Ideal for those seeking a blend of comfort and luxury, these units often come with great facilities and community vibes.
  • Cottages: These quaint retreats offer a cozy and charming ambiance, perfect for a peaceful getaway.**

Top attractions near Bucktown

Bucktown, Chicago, is perfect for family outings and urban adventures, offering a blend of culture and outdoor experiences. Explore stunning skyscrapers, relax in urban parks, and visit historic churches. This vibrant neighborhood caters to travelers seeking a rich city experience, making it an ideal destination for families looking to create lasting memories.

  • Michigan Avenue: Known as the Magnificent Mile, this bustling street is filled with high-end shops, dining, and vibrant city life, making it perfect for shopping enthusiasts and foodies alike.
  • Chicago Riverwalk: A scenic waterfront promenade ideal for families and outdoor lovers, featuring picturesque views, dining options, and the chance to enjoy boat tours along the iconic Chicago River.
  • Willis Tower: One of the tallest buildings in the U.S., offering stunning city views from its observation deck, providing an unforgettable experience of Chicago’s skyline.

Things to do recommended for couples

For a romantic getaway in Bucktown, enjoy a night at the Aragon Ballroom or House of Blues Chicago for live music just a few miles away. Don't forget to indulge in a meal at the historic Michael Jordan Restaurant, perfect for couples looking to savor the city's vibrant atmosphere.

Things to do recommended for families

Your family will love catching a game at Wrigley Field, just 2 miles away, or enjoying the serene surroundings of Northerly Island Natural Area, 6 miles from Bucktown. For some relaxation, visit The East Bank Club, located 3 miles away, perfect for unwinding together.

Things to do recommended for groups

Groups visiting Bucktown can enjoy a night at the Vic Theatre for cultural entertainment, laugh out loud at Second City’s comedy shows, and shop at the Chicago Place Mall for a blend of business and family-friendly vibes.

*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 Bucktown

If you're planning a trip with a group, family, pets, or seeking extended stays, be sure to prioritize your preferences when filtering your options. Here are some helpful Vrbo booking tips for you.

  • Traveling to Bucktown with a group: Think about how many bedrooms you'll require, as well as any additional features like a full kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Bucktown with young kids: Traveling with small children can be quite demanding. It's important to prioritize their comfort and safety, along with access to suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Bucktown: For many families, a vacation wouldn’t feel complete without their furry companion by their side. If this resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly properties offer feeding bowls and cozy beds to ensure that everyone feels at home.
  • Planning for a long term stay visiting Bucktown: If you're in search of vacation rentals that offer discounts 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 include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Bucktown

Exploring Bucktown, Chicago, offers a unique blend of urban charm and family-friendly vibes. This trendy neighborhood is known for its vibrant art scene, eclectic shops, and delicious dining options. Nearby neighborhoods like Wicker Park and Logan Square further enhance your experience with their scenic parks and welcoming atmosphere. Whether you’re enjoying outdoor excursions or soaking in the local culture, Bucktown promises an unforgettable vacation filled with friendly faces and exciting adventures.

  • Chicago: As a vibrant metropolis, Chicago is the backdrop for your Bucktown adventure. This city is known for its family-friendly atmosphere, outdoor spaces, and urban experiences. Explore the bustling shopping districts, catch a game at one of the local stadiums, or immerse yourself in the rich cultural offerings at various educational venues. Must-visit attractions include the renowned sports facilities and the lively tourist precinct, all of which provide a taste of the Windy City's charm and excitement.
  • Downtown Chicago: Located a mere 4 miles from Bucktown, Downtown Chicago is the city's bustling hub. It's a prime destination for families and outdoor enthusiasts alike. Here, you can enjoy a wealth of activities, from shopping in world-class boutiques to catching a show in one of the city's many theaters. The area is well-known for its vibrant tourist precinct, and visitors can easily access iconic stadiums and sports facilities that highlight Chicago's rich sports culture. Don't miss the chance to stroll along the scenic waterfront or visit Millennium Park.
  • West Bucktown: Just 0.6 miles from Bucktown, West Bucktown is a charming neighborhood that offers a blend of city life and community spirit. This area is perfect for families and those looking to enjoy outdoor activities. West Bucktown boasts excellent shopping opportunities, lively music concerts, and educational institutions. Key attractions include local stadiums and urban parks, which provide a great setting for relaxation and recreation. Experience the welcoming vibe of this neighborhood, where city-themed adventures await around every corner.

Best time to go to Bucktown

If you're planning a trip to Bucktown, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April, July and September, while off-peak times, like November to January tend to have fewer bookings and better deals.

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

Booking with Vrbo is simple

Are you hoping to save on your next getaway? It’s a great idea to stay flexible with your travel dates, as prices can vary. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Unlock savings with One Key

Plan your group getaway by booking an eligible Vrbo and earn OneKeyCash on your entire reservation. Being the planner has its rewards. When you join our travel rewards program, One Key, you’ll gain access to exclusive member discounts and accumulate OneKeyCash on qualifying bookings. Sign up today and start enjoying your savings.

Vrbo Trips: Effortless planning

Vrbo's Trip Board offers a practical way to plan your travels, allowing you to create new trips, continue from where you last paused, or manage your itinerary effortlessly. You can easily find your saved or booked properties neatly organized under Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply go to: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Bucktown?
In Bucktown, apartments are the most popular type of vacation rental, with around 12 available in this vibrant neighborhood known for its artistic flair and vibrant dining scene. Many of these apartments come equipped with modern amenities, including fully stocked kitchens, comfortable living spaces, and often access to shared outdoor areas or rooftops that provide nice views of the city.

In addition to apartments, there are several vacation houses, condos, and cottages that cater to travelers seeking more space or unique accommodations. These properties typically feature multiple bedrooms and outdoor spaces, making them suitable for families or groups looking to enjoy the charm of Bucktown while having the comforts of home.
How much does it cost to rent a vacation home in Bucktown?
Prices for vacation rentals in Bucktown 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 Bucktown 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 Bucktown vacation house rentals?
You can find great discounts on house rentals in Bucktown 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 Bucktown?
In Bucktown, popular vacation rental amenities include fully equipped kitchens, allowing travelers to prepare their own meals and enjoy the convenience of home cooking. Many rentals feature coffee and tea makers for a quick caffeine fix, and onsite parking is commonly available, making it easy for guests with vehicles. Properties often boast kitchen islands, providing additional space for meal prep or casual dining, as well as patios where guests can relax outdoors and enjoy the neighborhood's vibrant atmosphere.
Are there any family house rentals in Bucktown?
In Bucktown, Illinois, there are some family-friendly house rentals available, making it a great choice for those traveling with children. This vibrant neighborhood is known for its artistic vibe and proximity to various attractions. Many of these homes provide spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces for kids to enjoy.

Visitors will appreciate amenities like Wi-Fi and air conditioning, ensuring a comfortable stay. The locale is also conveniently located near parks, such as the popular Holstein Park, which features playgrounds and sports facilities, great for family outings. Additionally, Bucktown's energetic mix of shops and restaurants along Damen Avenue offers plenty of options for dining and entertainment, allowing families to explore local culture while having fun.
Can I rent a vacation home with a pool or hot tub in Bucktown?
In Bucktown, there are several vacation homes available for rent that feature pools and hot tubs. This trendy neighborhood in Chicago is known for its vibrant arts scene and vibrant dining options, making it an appealing destination for travelers. Many of these properties come with amenities such as private hot tubs, outdoor spaces for entertaining, and modern kitchens, great for relaxing after a day of exploring the city.
Are there any Bucktown vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Bucktown 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 Bucktown?
Yes, you can book pet-friendly vacation rentals in Bucktown. This vibrant neighborhood in Chicago offers a variety of accommodations that welcome pets, with around ten options available. Many of these rentals are equipped with modern amenities such as spacious living areas, fully equipped kitchens, and outdoor spaces where pets can enjoy some fresh air.

Bucktown is known for its artistic vibe and is close to parks like the nearby Holstein Park and the expansive Wicker Park, both of which provide excellent opportunities for walks and outdoor activities with your furry companions. The area is also home to a variety of pet-friendly cafes and shops, making it a great choice for travelers looking to explore the neighborhood with their pets.
Can I find long-stay vacation rentals in Bucktown?
A long-stay vacation rental in Bucktown 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 Bucktown for a vacation rental?
The best time to book a vacation rental in Bucktown is during the peak season from May to July, when the neighborhood comes alive with vibrant energy and outdoor activities. During these months, visitors can enjoy pleasant temperatures ranging from the mid-60s to the low 80s Fahrenheit, making it ideal for exploring the local parks, engaging in outdoor dining, and strolling through the artistic streets filled with boutiques and galleries.

July stands out as the most popular month in Bucktown, bustling with events and an atmosphere that invites travelers to immerse themselves in the local culture. The warm weather is great for enjoying the numerous festivals and outdoor markets that showcase the unique character of this lively Chicago neighborhood.

For those looking for a more affordable experience, consider visiting in November. This time offers a quieter ambiance, allowing you to enjoy Bucktown's charm at a more relaxed pace. You can explore local coffee shops, art installations, and unique shops without the crowds, and the cooler temperatures, typically in the mid-30s to low 50s Fahrenheit, provide a cozy backdrop for a leisurely visit.

Ultimately, the best time to visit Bucktown will depend on your preferences for activity and atmosphere—whether you seek the bustling energy of peak season or the peaceful charm of the quieter months.
Are there any remote work vacation rentals in Bucktown?
In Bucktown, Illinois, travelers seeking remote work vacation rentals will find a variety of options, with around 18 properties available in this vibrant neighborhood known for its lively atmosphere and artistic community. Many of these rentals come equipped with essential remote work amenities, such as high-speed Wi-Fi, dedicated desks, and comfortable office chairs, making them ideal for professionals looking to balance work and leisure. Some properties may also feature multiple workspaces, including computer monitors, providing a conducive environment for productivity.

Bucktown is ideally situated near unique coffee shops and co-working spaces, allowing for convenient breaks or productive outings. Additionally, the area is filled with parks and local boutiques, offering opportunities to unwind after a day of work. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Bucktown vacation rental?
Book your Bucktown 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 Bucktown?
In Bucktown, visitors can enjoy a blend of art, culture, and dining. The neighborhood is known for its vibrant arts scene, with galleries showcasing local artists and street art adorning many buildings. The 606 Trail, an elevated park and bike path, offers a unique outdoor space for walking, running, and cycling, while also providing access to various parks along the route.

Food enthusiasts will appreciate the diverse dining options, ranging from trendy cafes to upscale restaurants. The area is also home to boutique shops and vintage stores that reflect the neighborhood's unique character. For those interested in nightlife, there are several bars and music venues that contribute to Bucktown's lively atmosphere.
Can I change or cancel my Bucktown home rental booking on Vrbo?
To find Bucktown 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 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 Bucktown 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.

More Vacation Ideas

More Vacation Ideas