Wicker Park holiday rentals

We found 1,210 holiday rentals — enter your dates for availability
Discover a selection of 20 homes, 25 apartments and other holiday rentals in Wicker Park 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 amenities that you expect for your stay, which might include Wi-Fi and a washer and dryer. No matter what you're looking for, you'll find a property to rent to meet everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Wicker Park

Showing deals for:25 Dec - 1 Jan

Living area
Terrace/patio
Interior
Living area
Exceptional
(13 reviews)

6BD/5BTH + Roofdeck - Downtown Chicago!

Chicago

8% off
AU$21,474
for 7 nights, 1 apartment
AU$3,068 per night
includes taxes & fees
6BD/5BTH + Roofdeck - Downtown Chicago!
Dining
Our downtown Townhouse is in an amazing location
Room
Interior
Exceptional
(91 reviews)

Historic luxury townhouse on Chicago's Gold Coast

Chicago

5% off
AU$18,644
for 7 nights, 1 home
AU$2,663 per night
includes taxes & fees
Historic luxury townhouse on Chicago's Gold Coast
Interior
Dining
Interior
Exterior
Exceptional
(8 reviews)

5BR/4BA Modern SFH Logan Square!

Chicago

8% off
AU$5,971
for 7 nights, 1 home
AU$853 per night
includes taxes & fees
5BR/4BA Modern SFH Logan Square!
2 spots come with the unit- occupied by the van and SUV in this photo.
Top floor kitchen and dining area
Dining Area
Kitchen on Top Floor
Exceptional
(34 reviews)

The Exclusive- 7 Bed, 6 Bath Retreat

Chicago

5% off
AU$10,382
for 7 nights, 1 apartment
AU$1,483 per night
includes taxes & fees
The Exclusive- 7 Bed, 6 Bath Retreat
Living Room with 60 in Smart TV
Chef kitchen with Sub-Zero refrigerator, Wolf stove, Bosch dishwasher.
Living Room with 60 in Smart TV
Living Room with 60 in Smart TV
Exceptional
(92 reviews)

Stunning Lincoln Park Single-Family House with Fantastic Game Room

Chicago

11% off
AU$10,218
for 7 nights, 1 home
AU$1,460 per night
includes taxes & fees
Stunning Lincoln Park Single-Family House with Fantastic Game Room
View of Robey Hotel from back deck
3 bedroom unit is top floor of historic greystone
Living room area opens into dining room & kitchen
Living room area
Exceptional
(100 reviews)

Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.

Chicago

7% off
AU$6,342
for 7 nights, 1 home
AU$906 per night
includes taxes & fees
Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.
Upstairs queen bedroom 2
Downstairs living area
Fun Mirror Wall Upstairs
Downstairs living room
Exceptional
(99 reviews)

Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!

Chicago

7% off
AU$13,243
for 7 nights, 1 apartment
AU$1,892 per night
includes taxes & fees
Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
Dining
Interior
Room
Interior
Exceptional
(18 reviews)

Modern + Cozy Chicago stay w/garage parking & 20min to downtown

Chicago

7% off
AU$2,651
for 7 nights, 1 apartment
AU$379 per night
includes taxes & fees
Modern + Cozy Chicago stay w/garage parking & 20min to downtown
Living area
Interior
Private kitchen
Interior
Exceptional
(12 reviews)

Peaceful Living-2Bdrm/2Bath w/Private Parking, WiFi-Work Station-Wicker Park!

Chicago

7% off
AU$2,958
for 7 nights, 1 apartment
AU$423 per night
includes taxes & fees
Peaceful Living-2Bdrm/2Bath w/Private Parking, WiFi-Work Station-Wicker Park!
Private kitchen
Belmont Harbor
Living area
Living area
Exceptional
(192 reviews)

Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24

Chicago

15% off
AU$8,395
for 7 nights, 1 home
AU$1,199 per night
includes taxes & fees
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Living area
Room
Interior
Exterior
Exceptional
(6 reviews)

Peaceful Zen Flat | 2BR Oasis with Free Parking

Chicago

8% off
AU$3,984
for 7 nights, 1 apartment
AU$569 per night
includes taxes & fees
Peaceful Zen Flat | 2BR Oasis with Free Parking
Room
Living area
Private kitchen
Living area
Exceptional
(14 reviews)

Cozy apartment near zoo, DePaul, Oz Park and much more!

Chicago

7% off
AU$4,365
for 7 nights, 1 apartment
AU$624 per night
includes taxes & fees
Cozy apartment near zoo, DePaul, Oz Park and much more!
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

What is the most popular type of holiday rental in Wicker Park?
In Wicker Park, holiday houses are the most popular type of holiday rental, with about 28 available in the area. These properties often provide spacious living areas, fully equipped kitchens, and outdoor spaces such as gardens or patios, making them suitable for families or groups. Additionally, there are around 16 apartments scattered throughout the neighbourhood, offering a more compact option for those looking for a comfortable stay. These apartments typically feature modern amenities, including kitchen facilities and cosy living spaces, ideal for short-term visits.
Are there any beach house rentals in Wicker Park?
In Wicker Park, beach house rentals are available, although the area is not directly adjacent to the beach. These rentals typically offer a unique urban experience, with many located within vibrant neighbourhoods known for their artsy vibe and trendy shops. Amenities often include modern kitchens, spacious living areas, and outdoor spaces such as rooftops or patios, great for enjoying the lively option. While Wicker Park itself is more renowned for its cultural scene, those seeking a beach-like experience may find these rentals appealing for their proximity to the city's attractions and public transport options to nearby lakeside areas.
What are popular rental amenities in Wicker Park?
In Wicker Park, popular rental amenities include fully equipped kitchens, which allow guests to prepare their own meals with ease. Many rentals also feature balconies, providing a lovely outdoor space to relax and enjoy the vibrant neighbourhood. For those needing to work while away, accommodations often come with a desk and desk chair, suiting business travellers or those who simply prefer a dedicated workspace. Onsite parking is another prevalent amenity, making it convenient for guests with vehicles to access the area without hassle.
Can I find family house rentals in Wicker Park?
In Wicker Park, there are several family-friendly house rentals available, making it an appealing choice for those travelling with children. This vibrant neighbourhood is known for its energetic mix of shops, restaurants, and parks, providing plenty of entertainment options for families. Many of the homes feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where kids can play or enjoy a barbecue.Visitors will appreciate the close proximity to local attractions, such as the picturesque Wicker Park itself, which offers playgrounds, sports facilities, and a scenic area for picnics. Additionally, the neighbourhood's lively option includes numerous cafes and eateries, making it easy to find family-friendly dining options.
Can I rent a holiday home with a pool or hot tub in Wicker Park?
In Wicker Park, there are several holiday homes available for rent that feature pools or hot tubs, making it a great choice for travellers seeking relaxation and leisure. This vibrant neighbourhood in Chicago is known for its eclectic mix of dining, shopping, and nightlife, providing a lively option for visitors.Properties in Wicker Park often come equipped with amenities such as private hot tubs, outdoor patios for entertaining, and fully fitted kitchens, ideal for families or groups looking to enjoy their stay comfortably. Some rentals may also include additional features like barbecue grills and spacious living areas, ensuring a delightful experience for guests.
Can I book pet-friendly holiday rentals in Wicker Park?
In Wicker Park, there are several pet-friendly holiday rentals available, making it a great option for travellers looking to bring their furry companions along. This vibrant neighbourhood is known for its vibrant mix of boutiques, cafes, and lively street art, creating a special environment for visitors. Many of the holiday rentals here come equipped with amenities such as modern kitchens, spacious living areas, and outdoor spaces where pets can roam.Wicker Park is also close to several parks, including the expansive Wicker Park itself, which features walking paths, playgrounds, and green spaces great for a leisurely stroll with pets. The area is well-connected to public transport, allowing easy access to downtown Chicago and other attractions, further enriching the experience for both you and your pet.
When is the best time to visit Wicker Park for a holiday rental?
The best time to visit Wicker Park for a holiday rental is during the peak season from May to July, with July being the most popular month for travellers. This vibrant period attracts those keen to explore the neighbourhood's energetic offerings, including its renowned street festivals, bustling farmers' markets, and a diverse array of dining options. The warm weather, with temperatures typically ranging from 15 to 30 degrees Celsius, makes it ideal for outdoor activities, leisurely strolls, and enjoying the charming parks.Throughout the peak season, Wicker Park comes alive with an energetic atmosphere, great for those who relish a lively environment and the chance to meet fellow adventurers. Whether you're indulging in local cuisine or browsing unique boutiques along Milwaukee Avenue, the summer months offer a delightful blend of experiences.If you're looking for a more budget-friendly option, consider visiting in December. This month, while quieter, allows you to experience the holiday charm of Wicker Park, complete with festive decorations and local events that capture the spirit of the season.Ultimately, your ideal time to visit Wicker Park will depend on your preference for lively summer activities or the more tranquil, yet equally enchanting, atmosphere of the winter months.
Are there any remote work holiday rentals in Wicker Park?
In Wicker Park, Illinois, there are numerous options for remote work holiday rentals, with around 40 available in the area. This vibrant neighbourhood is known for its lively mix of shops, cafes, and parks, providing an inspiring environment for those working remotely. Many of the rentals come equipped with essential amenities such as free Wi-Fi, dedicated work desks, and comfortable desk chairs, allowing for a productive work-from-home experience.Additionally, Wicker Park is home to lovely green spaces like Wicker Park itself, where you can take breaks and enjoy the outdoors. The local coffee shops and eateries also provide great spots for a change of scenery while working. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are the top attractions in Wicker Park, Illinois, United States of America?
Wicker Park is a vibrant neighbourhood known for its lively mix of culture, art, and dining. One of the main attractions is Wicker Park itself, which features beautiful green spaces, walking paths, and a playground, making it a great spot for outdoor activities. Nearby, the historic Damen Avenue offers a variety of boutique shops and cafes, superb for leisurely strolls and local dining experiences.Art lovers can explore the numerous galleries and street art that adorn the area, while music enthusiasts might enjoy the live performances at local venues. The neighbourhood is also home to the renowned Flat Iron Arts Building, which hosts artist studios and exhibitions.
Are all fees included in the Wicker Park 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 Wicker Park holiday homes with parking?
Stayz offers a wide selection of holiday homes in Wicker Park 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 Wicker Park holiday homes?
You can find great discounts on holiday homes in Wicker Park 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 Wicker Park holiday home booking on Stayz?
To find Wicker Park 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 Wicker Park?
A long-stay holiday home in Wicker Park 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 Wicker Park holiday home?
Book your Wicker Park 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 Wicker Park?
Prices for holiday homes in Wicker Park 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 Wicker Park 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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