Wicker Park holiday homes

We found 1,231 holiday rentals — enter your dates for availability
Discover a selection of 20 homes, 23 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:18 Dec - 25 Dec

Exterior
Interior
Room
Terrace/patio
Exceptional
(39 reviews)

Private Historical Mansion,Luxury Home in Chicago’s Gold Coast, Event-Capable.

Chicago

8% off
NZ$44,552
for 7 nights, 1 home
NZ$6,365 per night
includes taxes & fees
Private Historical Mansion,Luxury Home in Chicago’s Gold Coast, Event-Capable.
It is huge! With lots of areas for relaxing and entertaining
Our downtown Townhouse is in an amazing location
Room
Dining
Exceptional
(91 reviews)

Historic luxury townhouse on Chicago's Gold Coast

Chicago

5% off
NZ$13,531
for 7 nights, 1 home
NZ$1,933 per night
includes taxes & fees
Historic luxury townhouse on Chicago's Gold Coast
Private kitchen
Dining
Interior
Exterior
Exceptional
(8 reviews)

5BR/4BA Modern SFH Logan Square!

Chicago

7% off
NZ$6,315
for 7 nights, 1 home
NZ$902 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
Bedroom 3 w/ Queen Bed
Exceptional
(34 reviews)

The Exclusive- 7 Bed, 6 Bath Retreat

Chicago

5% off
NZ$12,836
for 7 nights, 1 apartment
NZ$1,834 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
NZ$14,355
for 7 nights, 1 home
NZ$2,051 per night
includes taxes & fees
Stunning Lincoln Park Single-Family House with Fantastic Game Room
Dining room area
3 bedroom unit is top floor of historic greystone
Living room area
View of Robey Hotel from back deck
Exceptional
(100 reviews)

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

Chicago

7% off
NZ$7,978
for 7 nights, 1 home
NZ$1,140 per night
includes taxes & fees
Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.
Downstairs living room
Downstairs living area
Kitchen (upstairs)
Upstairs queen bedroom 2
Exceptional
(99 reviews)

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

Chicago

7% off
NZ$15,973
for 7 nights, 1 apartment
NZ$2,282 per night
includes taxes & fees
Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
Interior
Interior
Dining
Room
Exceptional
(18 reviews)

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

Chicago

7% off
NZ$3,183
for 7 nights, 1 apartment
NZ$455 per night
includes taxes & fees
Modern + Cozy Chicago stay w/garage parking & 20min to downtown
Private kitchen
Interior
Room
Interior
Exceptional
(12 reviews)

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

Chicago

7% off
NZ$3,687
for 7 nights, 1 apartment
NZ$527 per night
includes taxes & fees
Peaceful Living-2Bdrm/2Bath w/Private Parking, WiFi-Work Station-Wicker Park!
Private kitchen
Belmont Harbor
Exterior
Living area
Exceptional
(192 reviews)

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

Chicago

14% off
NZ$8,399
for 7 nights, 1 home
NZ$1,200 per night
includes taxes & fees
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Private kitchen
Exterior detail
Dining
Room
Exceptional
(71 reviews)

Wicker Park near Downtown and the Salt Shed Special 115.00 Sept 8-11

Chicago

7% off
NZ$3,200
for 7 nights, 1 apartment
NZ$457 per night
includes taxes & fees
Wicker Park near Downtown and the Salt Shed Special 115.00 Sept 8-11
Living area
Room
Private kitchen
Exterior
Exceptional
(6 reviews)

Peaceful Zen Flat | 2BR Oasis with Free Parking

Chicago

8% off
NZ$4,332
for 7 nights, 1 apartment
NZ$619 per night
includes taxes & fees
Peaceful Zen Flat | 2BR Oasis with Free Parking
Exterior
Living area
Private kitchen
Living area
Exceptional
(14 reviews)

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

Chicago

7% off
NZ$5,539
for 7 nights, 1 apartment
NZ$791 per night
includes taxes & fees
Cozy apartment near zoo, DePaul, Oz Park and much more!

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    Enjoy full kitchens, laundry, pools, gardens and more

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    More space, more privacy, more amenities — more value

Why visit Wicker Park

  • Lively streets and urban charm: Wander through Wicker Park's vibrant streets, where a mix of modern skyscrapers and quaint corners offers a uniquely urban experience.
  • Artistic flair: Soak up striking street art and local creative expressions that add a colourful touch to the neighbourhood.
  • Festive events: Enjoy local celebrations like the Wicker Park Fest, immersing yourself in the area's cultural buzz.
  • Green retreats: Relax in peaceful parks and green spaces, perfect for a leisurely family outing.
  • Dynamic atmosphere: Experience a blend of business and romantic vibes, reflecting the true spirit of urban Chicago.

Top attractions near Wicker Park

Wicker Park in Chicago, Illinois, is a vibrant neighbourhood perfect for family outings and urban adventures. Visitors can enjoy its lively atmosphere, featuring stunning skyscrapers and charming streets. The area hosts various events, including the popular Wicker Park Fest, offering a taste of local culture and entertainment. With its parks and city-themed attractions, Wicker Park provides a delightful experience for travellers seeking a blend of relaxation and exploration in an urban setting.

  • 875 North Michigan Avenue: Experience the dynamic city vibes of this skyscraper, a striking architectural marvel that offers a glimpse into urban Chicago, located a short distance from Wicker Park.
  • North Avenue Beach: Enjoy the inviting beach vibes at this popular urban beach, perfect for a swim or a relaxing stroll along the shore, situated a brief distance from Wicker Park.
  • Garfield Park Conservatory: Revel in the outdoor, family-friendly atmosphere at this lush conservatoryGarden, ideal for exploring diverse plant collections, located near Wicker Park.

Things to do recommended for couples

Wicker Park offers a delightful couple's experience with its charming parks and vibrant street art. Enjoy a leisurely stroll through the lush greenery of Wicker Park itself, or indulge in a cosy dinner at a local bistro. Don't forget to explore the quirky boutiques for unique finds together.

Things to do recommended for families

Explore the vibrant Wicker Park, where family-friendly cafes, boutique shops and urban parks await, creating a relaxed day out in a lively neighbourhood. Enjoy local flavours and a sense of community during your visit.

Things to do recommended for groups

Explore vibrant street art and chic boutiques in Wicker Park, Chicago. Enjoy lively gatherings at local cafes, and immerse in the creative scene and heritage of the neighbourhood 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 Wicker Park

Whether you're journeying with a group, travelling with family, taking your pets along, or seeking extended stays, be sure to apply the appropriate filters. Here are some Vrbo booking tips for you.

  • Traveling to Wicker Park with a group: Consider how many bedrooms you'll require, along with facilities such as a fully-equipped kitchen or an outdoor area for a group gathering. Luckily, you can use filters on Vrbo to select these and many more options.
  • Traveling to Wicker Park with young kids: Journeying with little ones can be quite demanding. It's important to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it’s wise to think about your closeness to attractions that are friendly for families.
  • Taking your pets with you to Wicker Park: Some families wouldn’t consider a trip complete without their furry mate by their side. If that sounds like you, then have a look at Vrbo properties that welcome pets. Most pet-friendly properties offer feeding bowls and beds, ensuring both you and your pet feel right at home.
  • Planning for a long term stay visiting Wicker Park: If you're after holiday rentals offering special rates for stays of a month or more, you've come to the right spot. With the proper filters, you can effortlessly locate and secure savings on monthly rentals. You might also want to consider including options like a parking space, a well-equipped kitchen, or your own private pool in your search.

Where to stay near Wicker Park

Wicker Park in Chicago is a vibrant neighbourhood perfect for family and urban getaways. Stroll through its lively streets, admire striking street art, and relax in green spaces. Enjoy a blend of business and romantic vibes, all while experiencing the friendly, city atmosphere unique to this iconic area of Chicago. Discover the heart of the neighbourhood and its exciting connection to urban culture during your visit.

  • Chicago: Chicago, a vibrant city where Wicker Park is nestled, offers a blend of family-friendly, outdoor, and urban themed experiences. Visitors can enjoy a variety of shopping areas, arena entertainment, and theatre performances. Within the city’s vicinity, you can explore a bustling sports stadium, a popular tourist precinct, and a scenic urban park, making it a well-rounded destination for a memorable holiday.
  • Downtown Chicago: Situated 5km from Wicker Park, Downtown Chicago is a lively neighbourhood that perfectly encapsulates the city's dynamic spirit. With a focus on family outings, outdoor adventures, and urban attractions, this area features prominent shopping venues, a vibrant arena for entertainment, and a theatre scene. Key landmarks include a historic tourist precinct, a major sports stadium, and a charming urban park, promising a rich travel experience.
  • Bucktown: Just 1km away from Wicker Park, Bucktown is a trendy neighbourhood known for its captivating mix of family-friendly, outdoor, and city themed activities. Enjoy a diverse selection of theatre shows, lively music concerts, and tranquil moments in a local recreation park. The area is also home to notable landmarks such as a picturesque urban park, a well-known sports facility stadium, and a venue for event conferences, offering a delightful escape for any traveller.

Best time to go to Wicker Park

If you're planning a trip to Wicker Park, it's a good idea to check both the weather and property rates. The warmest month is July.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January25.7°F (-3.5°C)Light RainMostly CloudySlightly Low
February27.0°F (-2.8°C)Light RainMostly CloudyAverage
March37.0°F (2.8°C)Light RainMostly CloudyAverage
April46.0°F (7.8°C)Light RainMostly SunnySlightly High
May57.0°F (13.9°C)Light RainMostly SunnyAverage
June67.3°F (19.6°C)Light RainMostly SunnySlightly High
July73.4°F (23.0°C)Light RainMostly SunnySlightly High
August73.0°F (22.8°C)Light RainMostly SunnyAverage
September67.1°F (19.5°C)Light RainMostly SunnyAverage
October54.9°F (12.7°C)Light RainMostly SunnyAverage
November42.3°F (5.7°C)Light RainMostly SunnySlightly Low
December33.1°F (0.6°C)Light RainMostly CloudySlightly Low

Booking with Vrbo is simple

If you’re aiming to save a few bucks on your upcoming getaway, think about being flexible with your travel dates since prices do vary. You can often save significantly by booking a longer stay. To locate the perfect Vrbo property that fits your budget, simply use our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board provides a convenient platform for you to plan new adventures, manage your travel arrangements, or review your bookings. Your saved or reserved properties are neatly categorized into Potential, Upcoming, or Current Trips. To check out the Trip Boards, simply head over to: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

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 Bookabach.
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 Bookabach?
Bookabach 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?
Bookabach 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 Bookabach, 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 Bookabach?
To find Wicker Park holiday rentals with free cancellation, just use Bookabach'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, Bookabach 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 Bookabach?
Bookabach'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 Bookabach 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. Bookabach offers something for every taste and budget, from affordable homes in Wicker Park to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach 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 Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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 Bookabach as a host?
Joining Bookabach 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, Bookabach 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 Bookabach 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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