Wicker Park holiday lettings

We found 1,215 holiday rentals — enter your dates for availability
Discover a selection of 20 homes, 22 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:15 Jan - 22 Jan

Terrace/patio
Exterior
Living area
Room
Exceptional
(41 reviews)

Chicago Gold Coast Luxury Private Mansion

Chicago

6% off
£16,587
for 7 nights, 1 home
£2,370 per night
includes taxes & fees
Chicago Gold Coast Luxury Private Mansion
Room
Our downtown Townhouse is in an amazing location
Interior
It is huge! With lots of areas for relaxing and entertaining
Exceptional
(93 reviews)

Historic luxury townhouse on Chicago's Gold Coast

Chicago

5% off
£3,788
for 7 nights, 1 home
£541 per night
includes taxes & fees
Historic luxury townhouse on Chicago's Gold Coast
Interior
River North Luxury Living
Outdoors at night
The building
Exceptional
(107 reviews)

River North's Rock N' Roll - In The Heart of the City

Chicago

7% off
£2,631
for 7 nights, 1 apartment
£376 per night
includes taxes & fees
River North's Rock N' Roll - In The Heart of the City
Kitchen (upstairs)
Downstairs living area
Downstairs living room
Fun Mirror Wall Upstairs
Exceptional
(101 reviews)

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

Chicago

7% off
£8,089
for 7 nights, 1 apartment
£1,156 per night
includes taxes & fees
Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
Living area
Interior
Interior
Private kitchen
Exceptional
(54 reviews)

Modern Logan Square Luxury: 5 bedroom - sleeps 16!

Chicago

7% off
£3,647
for 7 nights, 1 home
£521 per night
includes taxes & fees
Modern Logan Square Luxury: 5 bedroom - sleeps 16!
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
(93 reviews)

Stunning Lincoln Park Single-Family House with Fantastic Game Room

Chicago

10% off
£4,246
for 7 nights, 1 home
£607 per night
includes taxes & fees
Stunning Lincoln Park Single-Family House with Fantastic Game Room
Interior
Private kitchen
Dining
Interior
Wonderful
(50 reviews)

Gorgeous 5 BDR/ 4BA in Logan Square w/Parking!

Chicago

7% off
£2,682
for 7 nights, 1 home
£383 per night
includes taxes & fees
Gorgeous 5 BDR/ 4BA in Logan Square w/Parking!
Dining
Living area
Private kitchen
Interior
Exceptional
(14 reviews)

Wicker Park: Cozy Fireplace, Grand Piano

Chicago

25% off
£2,248
for 7 nights, 1 apartment
£321 per night
includes taxes & fees
Wicker Park: Cozy Fireplace, Grand Piano
Exterior
Living area
Private kitchen
Living area
Excellent
(11 reviews)

Spacious / New - 8BD/4BTH - Sleeps 16 + Garage!

Chicago

7% off
£3,717
for 7 nights, 1 home
£531 per night
includes taxes & fees
Spacious / New - 8BD/4BTH - Sleeps 16 + Garage!
Property grounds
Room
Interior
Terrace/patio
Exceptional
(76 reviews)

Private Historic Coach House Wicker Park

Chicago

6% off
£1,877
for 7 nights, 1 home
£268 per night
includes taxes & fees
Private Historic Coach House Wicker Park
View of Robey Hotel from back deck
3 bedroom unit is top floor of historic greystone
Dining room area
Living room area
Exceptional
(101 reviews)

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

Chicago

7% off
£4,658
for 7 nights, 1 home
£665 per night
includes taxes & fees
Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.
Living area
Belmont Harbor
Exterior
Living area
Exceptional
(193 reviews)

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

Chicago

8% off
£2,763
for 7 nights, 1 home
£395 per night
includes taxes & fees
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Interior
Living area
Dining
Kitchen
Exceptional
(32 reviews)

Sunny 2-Bedroom Logan Square Apartment – Your Perfect Chicago Base

Chicago

7% off
£1,211
for 7 nights, 1 apartment
£173 per night
includes taxes & fees
Sunny 2-Bedroom Logan Square Apartment – Your Perfect Chicago Base
Private kitchen
Interior
Room
Dining
Exceptional
(21 reviews)

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

Chicago

6% off
£870
for 7 nights, 1 apartment
£124 per night
includes taxes & fees
Modern + Cozy Chicago stay w/garage parking & 20min to downtown
Room
Interior
Interior
Private kitchen
Exceptional
(12 reviews)

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

Chicago

7% off
£1,648
for 7 nights, 1 apartment
£235 per night
includes taxes & fees
Peaceful Living-2Bdrm/2Bath w/Private Parking, WiFi-Work Station-Wicker Park!
Terrace/patio
Living area
Living area
Interior
Exceptional
(12 reviews)

Your Logan Square Oasis with Lush Outdoor Haven!

Chicago

7% off
£1,399
for 7 nights, 1 apartment
£200 per night
includes taxes & fees
Your Logan Square Oasis with Lush Outdoor Haven!
Living area
Living area
Room
Exterior
Exceptional
(14 reviews)

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

Chicago

7% off
£2,428
for 7 nights, 1 apartment
£347 per night
includes taxes & fees
Cozy apartment near zoo, DePaul, Oz Park and much more!
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Why visit Wicker Park

  • Eclectic Shopping: Discover unique boutiques and artisanal shops that offer one-of-a-kind finds.
  • Culinary Delights: Enjoy a diverse range of trendy cafes and restaurants serving delicious local cuisine.
  • Vibrant Art Scene: Immerse yourself in the local culture through galleries and street art.
  • Lush Green Spaces: Relax in Wicker Park, a picturesque park ideal for leisurely strolls and picnics.
  • Community Events: Experience the lively atmosphere at local events like the popular Wicker Park Fest.

Popular types of accommodation around Wicker Park

Welcome to Wicker Park, a vibrant neighbourhood in Chicago known for its eclectic mix of art, culture, and culinary delights. Here, you'll find a variety of accommodation options, including stylish apartments, charming private homes, and contemporary condos. Explore the bustling streets filled with unique boutiques, trendy cafes, and lively parks. Wicker Park offers an authentic Chicago experience, making it an ideal base for your adventure in the Windy City.

  • Flats: The most sought-after option in Wicker Park, flats offer a comfortable and convenient base for your stay.
  • Private Homes: A popular choice for families or groups, private homes provide ample space and a homely atmosphere.
  • Condominiums: Ideal for modern living, condominiums combine luxury and practicality in Wicker Park.
  • Cottages: For a quaint and charming experience, cottages are a delightful retreat in this vibrant neighbourhood.**

Top attractions near Wicker Park

Wicker Park, a vibrant neighbourhood in Chicago, offers a delightful mix of cultural experiences and outdoor activities, making it ideal for families and city explorers alike. Visitors can enjoy the lively atmosphere of local events, including the popular Wicker Park Fest, while exploring its urban parks and streets lined with unique shops and eateries. The area is perfect for immersing oneself in the local culture and enjoying a quintessential city experience.

  • Wicker Park: A vibrant neighbourhood known for its artsy atmosphere, Wicker Park features unique boutiques, trendy cafes, and lively music venues. The park itself is perfect for leisurely strolls and picnics, surrounded by beautiful trees and green spaces.
  • Wicker Park's Historic District: Explore the charming streets lined with stunning Victorian architecture, showcasing the rich history of the area. This district offers a glimpse into the past with its well-preserved buildings and inviting atmosphere.
  • Wicker Park Farmers Market: Enjoy fresh produce, local crafts, and delicious food from various vendors at this weekly market. It’s a delightful experience for food lovers and a great way to engage with the community.

Things to do recommended for couples

Wicker Park offers a charming escape for couples. Explore unique boutiques hand in hand, savour artisanal delights at local cafes, or enjoy a leisurely stroll through the park's lush greenery. In the evening, catch a live music show for a perfect romantic finish to your day.

Things to do recommended for families

Families will delight in the interactive exhibits at the Chicago Children's Museum, explore the vibrant murals in Wicker Park, or enjoy a leisurely stroll through the lush green spaces of the park, perfect for a picnic or playtime.

Things to do recommended for groups

Explore the vibrant street art scene on a guided mural tour, indulge in a food tasting at the local eateries, or enjoy a group bike ride along the scenic 606 Trail. Don't miss the unique shops and live music venues that Wicker Park has to offer.

*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

When planning your trip, whether you're travelling with a group, as a family, with your pets, or seeking extended stays, be sure to apply the appropriate filters based on your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Wicker Park with a group: Think about how many bedrooms you'll require, as well as features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for all these options and more on Vrbo.
  • Traveling to Wicker Park with young kids: Travelling with young children 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 how close you are to family-friendly attractions.
  • Taking your pets with you to Wicker Park: For many, a family holiday isn’t truly complete without their furry companion. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Wicker Park: If you’re in search of holiday rentals offering discounts for stays of a month or more, you’ve come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Additionally, you may want to consider including features such as a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay near Wicker Park

Wicker Park, a vibrant neighbourhood in Chicago, offers a delightful blend of urban charm and artistic flair. Visitors can explore eclectic boutiques, savour culinary delights in trendy cafes, and enjoy the lush greenery of Wicker Park itself. The area is perfect for families and couples alike, providing a dynamic atmosphere filled with friendly locals. With its rich cultural scene and picturesque streets, Wicker Park promises an unforgettable experience for every traveller.

  • Chicago: Chicago, a bustling metropolis, is the vibrant heart of the Midwest. Wicker Park, where you’ll be based, is known for its eclectic blend of art, culture, and cuisine. The city invites you to explore its renowned shopping districts, enjoy thrilling sports events at iconic stadiums, and take in captivating performances at world-class theatres. With urban parks scattered throughout, Chicago provides ample opportunities for outdoor activities, making it a perfect destination for families and city enthusiasts alike.
  • Downtown Chicago: Located merely 5km from Wicker Park, Downtown Chicago is a dynamic hub of activity. This neighbourhood offers a wealth of family-friendly attractions, shopping experiences, and entertainment options. You can immerse yourself in the vibrant atmosphere of its theatres or catch a game at a nearby sports facility. The scenic urban parks and tourist precincts make for delightful strolls, and the skyline views are simply breathtaking, ensuring a memorable visit for all.
  • West Town: Just 966m from Wicker Park, West Town is a charming neighbourhood that boasts a rich cultural scene. Known for its lively theatres and music concerts, it’s a hotspot for those seeking entertainment. With spacious recreation parks and event venues nearby, West Town is perfect for families wanting to enjoy outdoor activities and community events. The blend of arts, dining, and local charm makes West Town a delightful area to explore during your Chicago adventure.

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. Peak season runs in April and June to July, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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 SunnySlightly HighSlightly 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 SunnyAverageAverage
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 reduce costs on your upcoming journey? We recommend considering flexibility with your travel dates, as prices can vary significantly. Additionally, opting for a longer stay often results in considerable savings. To discover the ideal Vrbo property that fits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a convenient way to plan your journeys, pick up from where you last stopped, or manage your itineraries with ease. You can easily access properties you've previously saved or booked, now neatly categorised under Potential, Upcoming, or Current Trips. To start using Trip Boards, please visit: https://www.vrbo.com/en-gb/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.
How much does it cost to rent a holiday home in Wicker Park?
Prices for holiday rentals 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Wicker Park 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 Wicker Park holiday house rentals?
You can find great discounts on house rentals in Wicker Park 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 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.
Are there any Wicker Park holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals 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 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.
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.
Can I find long-stay holiday rentals in Wicker Park?
A long-stay holiday rental 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 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 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 Vrbo.
How early should I book a Wicker Park holiday rental?
Book your Wicker Park holiday 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 holiday rental, the better the price. *Based on analysis of Vrbo booking and occupancy data for 2024 stays.
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.
Can I change or cancel my Wicker Park home rental booking on Vrbo?
To find Wicker Park holiday 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 cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Wicker Park holiday 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way. Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

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