West Bucktown holiday rentals
We found 97 holiday rentals — enter your dates for availability
Discover a selection of 6 homes and other holiday rentals in West Bucktown that are perfect for your trip. Whether you're travelling with your children and pets, with friends or just your children, holiday homes have the best amenities for hanging out with the people that matter most, which might include a hot tub and a washer and dryer. No matter what you're looking for, you'll find a property to rent for everyone's needs, including accessible or non-smoking choices.
Holiday rentals with weekly discounts – West Bucktown
Showing deals for:13 Nov - 20 Nov

Exceptional
(54 reviews)
Modern Logan Square Luxury: 5 bedroom - sleeps 16!
Chicago
AU$7,841
for 7 nights, 1 home
AU$1,120 per night
includes taxes & fees

Exceptional
(5 reviews)
5BR/4BA Modern SFH Logan Square!
Chicago
AU$4,532
for 7 nights, 1 home
AU$647 per night
includes taxes & fees

Exceptional
(96 reviews)
Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.
Chicago
AU$6,352
for 7 nights, 1 home
AU$907 per night
includes taxes & fees

Exceptional
(10 reviews)
Peaceful Living-2Bdrm/2Bath w/Private Parking, WiFi-Work Station-Wicker Park!
Chicago
AU$2,988
for 7 nights, 1 apartment
AU$427 per night
includes taxes & fees

Wonderful
(49 reviews)
Gorgeous 5 BDR/ 4BA in Logan Square w/Parking!
Chicago
AU$6,145
for 7 nights, 1 home
AU$878 per night
includes taxes & fees

Exceptional
(22 reviews)
Sunny 2-Bedroom Logan Square Apartment – Your Perfect Chicago Base
Chicago
AU$2,502
for 7 nights, 1 apartment
AU$357 per night
includes taxes & fees
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Find the best place to stay - West Bucktown

Bright/Cozy/Hip 2/1 Apt | Logan Square
Sleeps 5 · 2 bedrooms · 1 bathroom

Smart Home in Logan Square by the 606 Trail
Sleeps 8 · 3 bedrooms · 2+ bathrooms

Beautiful duplex in the heart of bucktown.
Sleeps 10 · 2 bedrooms · 2 bathrooms

Sunny 2-Bedroom Logan Square Apartment – Your Perfect Chicago Base
Sleeps 4 · 2 bedrooms · 1 bathroom

The Logan Square Guest House - Classic Vintage Comfort With Free Parking!
Sleeps 5 · 2 bedrooms · 1 bathroom

Unique And Amazing Gigantic Sunlit Loft ~ One Of A Kind ~ Excellent Location!
Sleeps 16 · 6 bedrooms · 2+ bathrooms
Top rated rentals - West Bucktown

Wonderful stay!
Super neat, clean, easy check in and out, wonderful hosts, amazing location! I would definitely recommend! Oh and the sauna is a fantastic plus! Thank you for having us!
Meenakshi C.
Stayed May 2025
- 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, gardens and more
- More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
What is the most popular type of holiday rental in West Bucktown?
In West Bucktown, both holiday houses and apartments are equally popular, with around 12 of each type available in this vibrant neighbourhood. The apartments typically offer modern amenities such as fully equipped kitchens, comfortable living spaces, and often access to communal gardens or rooftop areas for relaxation.On the other hand, the holiday houses tend to provide more space, featuring multiple bedrooms, private outdoor spaces, and amenities like barbeque areas—ideal for families or groups looking for a home away from home.
What are popular rental amenities in West Bucktown?
In West Bucktown, popular holiday rental amenities include fully equipped kitchens, superb for preparing meals, and coffee and tea makers to enjoy a warm beverage at any time. Many rentals also feature decks or patios, providing outdoor space to relax or entertain. Onsite parking is commonly available, making it convenient for those travelling by car. Additionally, accommodations often include a desk, suiting business travellers or anyone needing a dedicated workspace.
Can I find family house rentals in West Bucktown?
In West Bucktown, visitors will find several family-friendly house rentals that cater to various needs. This vibrant neighbourhood is known for its tree-lined streets and proximity to parks, making it an ideal spot for families. Many of the properties boast spacious living areas, fully equipped kitchens for preparing meals together, and outdoor spaces where children can play safely.Additionally, families can enjoy nearby attractions such as the expansive Walsh Park, which features playgrounds and sports facilities, adding to the overall appeal of the area.
Can I rent a holiday home with a pool or hot tub in West Bucktown?
In West Bucktown, there are several holiday homes available for rent that feature pools and hot tubs. This vibrant neighbourhood, known for its trendy atmosphere and proximity to the city centre of Chicago, offers a variety of amenities to enhance your stay. Many properties come equipped with private hot tubs, outdoor spaces for relaxation, and modern kitchens suitable for self-catering. Visitors can also expect comfortable living areas, Wi-Fi, and air conditioning to ensure a pleasant experience.
Can I book pet-friendly holiday rentals in West Bucktown?
In West Bucktown, there are several pet-friendly holiday rentals available for those looking to enjoy a stay in this vibrant neighbourhood. Many of these rentals come equipped with modern amenities such as fully furnished kitchens, spacious living areas, and outdoor spaces where pets can relax. The area is known for its tree-lined streets and proximity to parks, making it ideal for pet owners who wish to take their furry friends for walks.Nearby, the expansive Humboldt Park offers ample green space, walking trails, and a dog-friendly environment, providing great opportunities for outdoor activities with pets. West Bucktown also has various pet-friendly cafes and shops, ideal for travellers accompanied by their pets.
When is the best time to visit West Bucktown for a holiday rental?
The best time to visit West Bucktown for a holiday rental is during the peak season from May to July. This vibrant period attracts a diverse crowd, including families and adventure seekers, all eager to explore the lively neighbourhood filled with unique shops, parks, and cultural events. July stands out as the most popular month, where you can enjoy warm summer temperatures, typically ranging between 20 to 30 degrees Celsius, great for outdoor activities and leisurely strolls.During this time, you'll find plenty of options for outdoor dining and local festivals that highlight the area's artistic flair. The community comes alive with events that cater to various interests, making it an excellent choice for those looking to immerse themselves in a rich cultural experience.If you're seeking a more budget-friendly option, consider visiting in December. During this time, this month offers a unique charm as the holiday season transforms West Bucktown into a winter wonderland. You can enjoy festive decorations, local holiday markets, and a relaxed atmosphere that's great for intimate gatherings with friends and family.Ultimately, your ideal visit to West Bucktown will depend on whether you prefer the bustling energy of summer or the serene beauty of the holiday season.
Are there any remote work holiday rentals in West Bucktown?
In West Bucktown, Illinois, there are around 20 holiday rentals that cater specifically to remote work needs. This neighbourhood is known for its vibrant setting and convenient access to various amenities. Many of the available properties come equipped with essential remote work amenities such as free Wi-Fi, dedicated workspaces with desks and chairs, and some even offer access to printers, making them suitable for professionals looking to balance work and leisure.The area is also well-connected, allowing for easy exploration of nearby parks, local cafes, and shops, which can provide a nice break from work. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are the top attractions in West Bucktown, Illinois, United States of America?
In West Bucktown, visitors can enjoy a blend of local charm and urban convenience. The neighbourhood is known for its vibrant arts scene, with numerous galleries and studios showcasing the work of local artists. Just a short stroll away, the 606 Trail offers an elevated park experience for walking, jogging, and cycling, providing scenic views of the city.Nearby, the renowned Wicker Park area is filled with trendy boutiques, cafes, and restaurants, making it a popular spot for dining and shopping. The historic churches and unique architecture in the area add to its character, while local parks like Maplewood Park provide green spaces for relaxation and recreation.For those interested in nightlife, West Bucktown is close to a variety of bars and music venues that host live performances, contributing to the lively option.
Are all fees included in the West Bucktown holiday homes prices shown on Stayz?
Stayz 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.
Are there any West Bucktown holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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 any discounts for West Bucktown holiday homes?
You can find great discounts on holiday homes in West Bucktown on Stayz, 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.
Can I change or cancel my West Bucktown holiday home booking on Stayz?
To find West Bucktown holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in West Bucktown?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising 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 favourites, and build the perfect itinerary together.
How early should I book a West Bucktown holiday home?
Book your West Bucktown holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in West Bucktown?
Prices for holiday homes 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. Stayz offers something for every taste and budget, from affordable homes in West Bucktown to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
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