Photo by Marc Jacobs
West Bucktown vacation rentals
We found 119 vacation rentals — enter your dates for availability
Discover a selection of 9 homes and other vacation rentals in West Bucktown that are perfect for your trip. Whether you’re traveling with friends, family, or just with your pet, vacation homes have the best amenities for spending time at your vacation home, which might include parking and a fireplace. No matter what you're looking for, you'll be able to choose a rental that has what everyone needs, including a place that is accessible or non-smoking.
Vacation rentals with weekly discounts - West Bucktown
Showing deals for:Nov 14 - Nov 21
Image gallery for Clean, Private, Cozy Urban Oasis Chicago Greystone In Heart of Logan Square
1010 out of 10 rating
Exceptional
(42 reviews)
Clean, Private, Cozy Urban Oasis Chicago Greystone In Heart of Logan Square
Chicago, IL
19% off
Price is CA $300
CA $300
CA $3,066 total
CA $3,066 total
includes taxes & fees
Image gallery for Spacious 8 BDRM + 2 Kitchens + Garage! Sleeps 16!
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Spacious 8 BDRM + 2 Kitchens + Garage! Sleeps 16!
Chicago, IL
10% off
Price is CA $659
CA $659
CA $6,732 total
CA $6,732 total
includes taxes & fees
Image gallery for Bright 4 bed family home in Logan Sq w/private backyard & grill.Free parking
9.69.6 out of 10 rating
Exceptional
(7 reviews)
Bright 4 bed family home in Logan Sq w/private backyard & grill.Free parking
Chicago, IL
19% off
Price is CA $732
CA $732
CA $7,623 total
CA $7,623 total
includes taxes & fees
Image gallery for Unique And Amazing Gigantic Sunlit Loft ~ One Of A Kind ~ Excellent Location!
9.89.8 out of 10 rating
Exceptional
(53 reviews)
Unique And Amazing Gigantic Sunlit Loft ~ One Of A Kind ~ Excellent Location!
Chicago, IL
10% off
Price is CA $1,486
CA $1,486
CA $14,414 total
CA $14,414 total
includes taxes & fees
Image gallery for ❤️🔥MAGNIFICENT NEW Home w/8 Beds & Free Parking❤️🔥
9.69.6 out of 10 rating
Exceptional
(35 reviews)
❤️🔥MAGNIFICENT NEW Home w/8 Beds & Free Parking❤️🔥
Chicago, IL
15% off
Price is CA $627
CA $627
CA $6,089 total
CA $6,089 total
includes taxes & fees
Image gallery for Huge & Luxurious Logan Sq home,2 car garage,PRIVATE rooftop deck,great location!
1010 out of 10 rating
Exceptional
(6 reviews)
Huge & Luxurious Logan Sq home,2 car garage,PRIVATE rooftop deck,great location!
Chicago, IL
5% off
Price is CA $964
CA $964
CA $9,448 total
CA $9,448 total
includes taxes & fees
Image gallery for The Avondale Guesthouse
9.69.6 out of 10 rating
Exceptional
(40 reviews)
The Avondale Guesthouse
Chicago, IL
20% off
Price is CA $165
CA $165
CA $1,759 total
CA $1,759 total
includes taxes & fees
Image gallery for The Logan Square Guest House - Classic Vintage Comfort With Free Parking!
1010 out of 10 rating
Exceptional
(30 reviews)
The Logan Square Guest House - Classic Vintage Comfort With Free Parking!
Chicago, IL
5% off
Price is CA $368
CA $368
CA $3,668 total
CA $3,668 total
includes taxes & fees
Image gallery for Chic and Spacious Bi-level 3BD in Bucktown!
1010 out of 10 rating
Exceptional
(6 reviews)
Chic and Spacious Bi-level 3BD in Bucktown!
Chicago, IL
10% off
Price is CA $342
CA $342
CA $3,559 total
CA $3,559 total
includes taxes & fees
Image gallery for Luxury Designer Penthouse Loft | Sleeps 20
9.89.8 out of 10 rating
Exceptional
(9 reviews)
Luxury Designer Penthouse Loft | Sleeps 20
Chicago, IL
10% off
Price is CA $830
CA $830
CA $8,031 total
CA $8,031 total
includes taxes & fees
Image gallery for Cozy Wicker Park Home with Movie Room
9.89.8 out of 10 rating
Exceptional
(9 reviews)
Cozy Wicker Park Home with Movie Room
Chicago, IL
40% off
Price is CA $473
CA $473
CA $5,290 total
CA $5,290 total
includes taxes & fees
Image gallery for Chic Urban Stay: Queen Beds, Near Train, EV Charge
1010 out of 10 rating
Exceptional
(5 reviews)
Chic Urban Stay: Queen Beds, Near Train, EV Charge
Chicago, IL
10% off
Price is CA $542
CA $542
CA $5,525 total
CA $5,525 total
includes taxes & fees
Image gallery for Stylish, Inviting 2-BR near Logan Square and Wrigley Field
1010 out of 10 rating
Exceptional
(58 reviews)
Stylish, Inviting 2-BR near Logan Square and Wrigley Field
Chicago, IL
10% off
Price is CA $187
CA $187
CA $1,920 total
CA $1,920 total
includes taxes & fees
Image gallery for Uniquely Spacious Two-Story Loft in Wicker Park
9.29.2 out of 10 rating
Wonderful
(5 reviews)
Uniquely Spacious Two-Story Loft in Wicker Park
Chicago, IL
15% off
Price is CA $454
CA $454
CA $4,808 total
CA $4,808 total
includes taxes & fees
Image gallery for Bucktown Private Condo
1010 out of 10 rating
Exceptional
(12 reviews)
Bucktown Private Condo
Chicago, IL
10% off
Price is CA $282
CA $282
CA $2,860 total
CA $2,860 total
includes taxes & fees
Image gallery for Light and bright 3BD duplex in Avondale, Chicago
1010 out of 10 rating
Exceptional
(24 reviews)
Light and bright 3BD duplex in Avondale, Chicago
Chicago, IL
21% off
Price is CA $204
CA $204
CA $2,156 total
CA $2,156 total
includes taxes & fees
Image gallery for Bright 2 bed conveniently located in the heart of Logan Square with easy parking
1010 out of 10 rating
Exceptional
(24 reviews)
Bright 2 bed conveniently located in the heart of Logan Square with easy parking
Chicago, IL
10% off
Price is CA $208
CA $208
CA $2,109 total
CA $2,109 total
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - West Bucktown
Beautiful duplex in the heart of bucktown.
Sleeps 12 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
Huge & Luxurious Logan Sq home,2 car garage,PRIVATE rooftop deck,great location!
Sleeps 12 · 5 bedrooms · 4 bathrooms
1010 out of 10
Exceptionalexceptional
6 reviews(6 reviews)
Old Town Elegance Awaits You in This Classic Chicago Stunner! by AllSet Turnover
Sleeps 3 · 1 bedroom · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
8 reviews(8 reviews)
Mid Century Modern Penthouse-Logan Square Chicago
Sleeps 4 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
7 reviews(7 reviews)
Free Parking & Wifi in Bucktown/Logan Square Apt, Close to Everything!
Sleeps 5 · 2 bedrooms · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
65 reviews(65 reviews)
Walk to Blue Line: Sleek Apartment in Bucktown!
Sleeps 6 · 2 bedrooms · 1 bathroom
7.67.6 out of 10
Goodgood
7 reviews(7 reviews)
Top rated rentals - West Bucktown
Bucktown gem
1010 out of 10
Exceptionalexceptional
12 reviews(12 reviews)
Convenient, quiet, clean and close to all of the best that Bucktown has to offer. It was in a perfect location for our needs and I've already recommended to family and friends. We look forward to returning on our next trip to Chicago.
Phyllis B.
Stayed May 2025
Perfect for our family
1010 out of 10
Exceptionalexceptional
42 reviews(42 reviews)
The apartment was perfect for our family including lots of room for our 2 teenagers to spread out and relax. It was very clean and easily accessible to the blue line transit to downtown and O”Hare. There were many great restaurants nearby and our host was super responsive. We’d love to stay again.
Melissa T.
Stayed Aug 2023
Great place in a great neighborhood!
1010 out of 10
Exceptionalexceptional
76 reviews(76 reviews)
Very nice, spacious, top floor of a house. In a great neighborhood, seconds to the train and a huge range of places to eat and drink. Amy is an incredibly friendly and helpful host!.Would love to stay there again.
Tim H.
Stayed Jun 2023
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
What is the most popular type of vacation rental in West Bucktown?
In West Bucktown, vacation houses and apartments are both popular choices, with several of each type available throughout the neighbourhood. Many apartments are situated close to local parks and trendy shops, offering amenities like fully equipped kitchens, comfortable living areas, and access to communal spaces such as rooftop terraces. These rentals typically provide a modern, urban feel, appealing to those looking for a city vibe.
How much does it cost to rent a vacation home in West Bucktown?
Prices for vacation rentals in West 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 travelling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in West Bucktown to more spacious homes.
Are there any discounts for West Bucktown vacation house rentals?
You can find great discounts on house rentals in West 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 West Bucktown?
In West Bucktown, popular rental amenities include fully equipped kitchens, allowing guests to prepare their own meals, along with coffee and tea makers for a warm beverage any time of day. Many properties also feature blenders for those who enjoy smoothies or other blended drinks. Onsite parking is a convenient option for those travelling by car, and outdoor patios provide a lovely space to relax and enjoy the neighbourhood's charm.
Are there any family house rentals in West Bucktown?
In West Bucktown, there are several family-friendly house rentals available, with around eleven options to choose from. This vibrant neighbourhood offers a mix of modern amenities and easy access to local attractions, making it ideal for families. Properties often include spacious living areas and fully equipped kitchens, allowing for comfortable family meals and gatherings. Many homes also feature outdoor spaces, great for children to play and for parents to unwind.
Can I rent a vacation home with a pool or hot tub in West Bucktown?
In West Bucktown, there are several vacation homes available for rent that feature hot tubs, providing an excellent option for relaxation after a day of exploring the area. This vibrant neighbourhood, known for its artistic flair and proximity to the city's attractions, offers a variety of properties that cater to different group sizes and preferences.
Are there any West Bucktown vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in West Bucktown 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.
Are there pet-friendly vacation rentals in West Bucktown?
In West Bucktown, travellers can indeed find several pet-friendly vacation rentals available. This vibrant neighbourhood offers a variety of accommodations, including modern apartments and charming houses, many of which feature amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces for relaxation.
Can I find long-stay vacation rentals in West Bucktown?
A long-stay vacation rental in West Bucktown 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.
When is the best time to visit West Bucktown for a vacation rental?
The best time to visit West Bucktown for a vacation rental is during the peak season from May to July. This vibrant period attracts many visitors eager to enjoy the neighbourhood's lively atmosphere, with an abundance of outdoor activities, dining options, and cultural events. With temperatures typically ranging from the mid-teens to low 30s Celsius, the warm weather creates the great backdrop for exploring the local parks and vibrant street scenes.
July is particularly popular, as the summer reaches its zenith. You can immerse yourself in the local culture, with many outdoor festivals and events taking place, creating a bustling environment filled with energy and excitement. The longer daylight hours allow for plenty of time to enjoy everything West Bucktown has to offer, making it an ideal time for families and friends travelling together.
For those looking for a more budget-friendly option, consider visiting in December. While this month falls within the low season, it offers unique charms, such as festive vacation decorations and a quieter atmosphere. You can enjoy the local shops and cafes at a more leisurely pace, making it a lovely time for a peaceful retreat.
Are there any remote work vacation rentals in West Bucktown?
In West Bucktown, there are several remote work vacation rentals available, with around 15 options to choose from. This vibrant neighbourhood in Chicago offers a unique blend of urban living and accessibility to nature. Properties typically feature amenities tailored for remote workers, including high-speed Wi-Fi, dedicated desks, ergonomic chairs, and sometimes even office spaces equipped with computer monitors. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a West Bucktown vacation rental?
Book your West 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 West Bucktown?
In West Bucktown, visitors can enjoy a mix of local charm and vibrant culture. One of the popular attractions is the 606, an elevated park and trail system that offers walking, jogging, and cycling paths, providing stunning views of the surrounding neighbourhoods. This area is also known for its artistic flair, with various galleries and street art that reflect the community's creative spirit.
For those interested in shopping and dining, the neighbourhood boasts a range of independent boutiques and trendy cafes along its main thoroughfares. Additionally, the nearby Wicker Park area enhances the experience with its lively atmosphere, featuring music venues, bars, and restaurants that showcase the local culinary scene.
Can I change or cancel my West Bucktown home rental booking on Vrbo?
To find West 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 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 West 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.