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Wicker Park holiday lettings

We found 1,396 holiday rentals — enter your dates for availability

Discover a selection of 19 homes, 35 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:7 Nov - 14 Nov

Image gallery for 2 Rooftops, 2 Car Garage, 4 Stories|Down-Townhome

Living area
8.0 out of 10 rating
Very good
(14 reviews)

2 Rooftops, 2 Car Garage, 4 Stories|Down-Townhome

Chicago, IL

10% off
Price is £2,495
£356 per night
includes taxes & fees
2 Rooftops, 2 Car Garage, 4 Stories|Down-Townhome

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Find out more about Wicker Park

Find out more about Wicker Park

Why visit Wicker Park

  • Urban charm: Wicker Park offers a vibrant mix of striking architecture and lively streets, perfect for exploration.
  • Family-friendly activities: Enjoy a range of events and attractions suitable for all ages, ensuring a memorable visit.
  • Stunning parks: Experience lush urban parks that provide a refreshing escape from the bustling city.
  • Diverse accommodation: Choose from stylish apartments and unique holiday rentals to suit various preferences.
  • Nearby neighbourhoods: Explore charming nearby areas like Oak Park and Lincoln Park for additional scenic experiences.

Popular types of accommodation around Wicker Park

Wicker Park boasts a fantastic selection of vacation rentals, perfect for any traveller seeking a unique experience in Chicago. From stylish apartments and comfortable houses to modern condos, there's something to suit every preference. Whether you're searching for Wicker Park apartments, rentals, or apartments for rent, you'll find various options to accommodate your needs. Explore the charm of this vibrant neighbourhood while enjoying the convenience and flexibility of your chosen accommodation.

  • Apartments: The top choice for holidaymakers in Wicker Park, offering modern amenities and a convenient base for exploring the area.
  • Houses: Ideal for families or groups seeking a home-like atmosphere, these properties provide ample space and comfort.
  • Condos: A popular option, these self-contained units offer a blend of luxury and practicality in the heart of the neighbourhood.
  • Cottages: Quaint and charming, these lovely retreats provide a cosy escape for those looking to unwind.**

Top attractions near Wicker Park

Wicker Park is ideal for families and those seeking an urban outdoor experience. This vibrant area offers an array of attractions, including striking skyscrapers, bustling streets, and lush urban parks. Visitors can immerse themselves in the local culture and enjoy family-friendly activities. Don't miss out on the various events happening in Wicker Park during your stay, ensuring a memorable visit for everyone.

  • Michigan Avenue: A bustling thoroughfare known for its vibrant atmosphere, featuring high-end shops, dining options, and iconic landmarks, making it a must-visit for urban explorers.
  • Chicago Riverwalk: This scenic promenade offers a delightful outdoor experience, perfect for families. Stroll along the water, enjoy cafes, and take in stunning views of the city.
  • Willis Tower: Once the tallest building in the world, this skyscraper provides an exhilarating experience with its Skydeck, offering panoramic views of Chicago's remarkable skyline.

Things to do recommended for couples

Wicker Park offers a delightful escape for couples. Enjoy live music at the Aragon Ballroom or the House of Blues, both within a short distance. For a romantic meal, the Historic Michael Jordan Restaurant, with its charming atmosphere, is a perfect choice just a few miles away.

Things to do recommended for families

Families will love the excitement of Wrigley Field, just 1.9km from Wicker Park, or unwind at the Northerly Island Natural Area, 3.1km away, perfect for relaxation. For fitness enthusiasts, The East Bank Club is a mere 1.2km from Wicker Park, offering wellness activities.

Things to do recommended for groups

In Wicker Park, groups can enjoy a delightful evening at the Vic Theatre, just 1.9km away, for some cultural entertainment. A visit to the Second City comedy club, 1.2km away, promises laughter, while the 900 North Michigan Shops, also 1.9km away, offers a fantastic shopping experience.

What do I need to keep in mind when booking a vacation around Wicker Park

When travelling with a group, family, pets, or seeking extended stays, it’s important to apply the appropriate filters based on your priorities. Here are some helpful booking tips for using Vrbo.

  • Traveling to Wicker Park with a group: Think about how many bedrooms you require, along with features like a fully equipped kitchen or outdoor area for group gatherings. Thankfully, you can easily refine your search for all of these options, and many 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 for their age, like a private swimming pool. Additionally, it's wise to think about how close you are to attractions that are suitable for families.
  • Taking your pets with you to Wicker Park: For many, a family holiday wouldn’t feel complete without their furry companion. If that resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds to ensure 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 spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include options such as a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Wicker Park

Wicker Park offers a delightful blend of urban charm and family-friendly vibes, perfect for a memorable holiday. Explore stunning architecture and vibrant neighbourhoods, with nearby gems like Oak Park and Lincoln Park providing picturesque scenery and a welcoming atmosphere. Whether you're seeking a romantic getaway or a lively city adventure, Wicker Park is sure to captivate with its unique character and friendly locals.

  • Chicago: Chicago, a vibrant metropolis located 1.9km from Wicker Park, is known for its rich culture and bustling atmosphere. Visitors flock to this city for family-friendly activities, outdoor adventures, and captivating urban experiences. Notable attractions include expansive shopping areas and entertainment venues, such as sports facilities and stadiums, perfect for catching a game or concert. The city's iconic skyline and diverse neighbourhoods offer a unique backdrop for exploring art, history, and cuisine, making Chicago an essential stop on your travels.
  • Downtown Chicago: Just 1.9km from Wicker Park, Downtown Chicago is the heartbeat of the city, offering an exhilarating blend of shopping, dining, and cultural experiences. This lively neighbourhood is ideal for families and outdoor enthusiasts alike, with easy access to theatres and entertainment facilities. Attractions such as tourist precincts and sports stadiums make it a hub for events and activities. Stroll along the famous Magnificent Mile, visit Millennium Park, or enjoy a river cruise to take in the stunning architecture and vibrant atmosphere that Downtown Chicago has to offer.
  • West Town: West Town, located a mere 373m from Wicker Park, is a charming neighbourhood that embodies the spirit of Chicago with its eclectic mix of culture and community. Ideal for families and city explorers, West Town boasts a variety of theatres, music venues, and trendy shopping areas. The local parks provide a delightful escape for outdoor activities, while sports facilities and stadiums offer entertainment for fans. The vibrant art scene and diverse dining options make West Town a must-visit destination for those seeking an authentic Chicago experience.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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 a breeze

Are you hoping to cut costs on your upcoming holiday? Being flexible with your travel dates can often lead to significant savings, as prices can vary. Additionally, opting for a longer stay typically allows for even greater discounts. To discover the perfect Vrbo property that fits your budget, utilise our filters to sort by price, location, and type of accommodation.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board provides an excellent platform for you to craft new journeys, manage your existing plans, or review and organise your bookings. Your saved or booked properties are conveniently categorised into Potential, Upcoming, or Current Trips. To discover more about 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 quite popular, alongside several apartments and condos available throughout the area. The neighbourhood is known for its vibrant atmosphere, with many properties located near bustling streets filled with trendy shops, restaurants, and bars. Most holiday houses typically offer spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor spaces, making them ideal for families or larger groups. Meanwhile, apartments and condos often feature modern amenities such as communal fitness centres, rooftop terraces, and in-unit laundry facilities, providing a comfortable and convenient stay.
Are there any beach house rentals in Wicker Park?
In Wicker Park, Illinois, there are beach house rentals available, offering a great experience in this vibrant neighbourhood. While Wicker Park is primarily known for its urban charm, a selection of holiday rentals can be found nearby, featuring amenities that cater to various needs. Most of these properties include fully equipped kitchens, spacious living areas, and modern furnishings, providing a comfortable stay for guests. Some rentals may also offer outdoor spaces, ideal for enjoying the warm weather and socialising with friends or family.
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 featuring essential appliances such as blenders and coffee makers, along with kitchen islands for added convenience. Many properties also offer onsite parking, making it easier for guests to explore the vibrant neighbourhood and nearby attractions.
Are there any family house rentals in Wicker Park?
In Wicker Park, there are twelve family-friendly house rentals available, making it a great choice for those travelling with children. This vibrant neighbourhood is known for its lively mix of shops, eateries, and parks, ensuring plenty of activities for families. Many of the homes feature spacious living areas, fully equipped kitchens for preparing meals, and outdoor spaces where kids can play or families can enjoy a barbecue.
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 and hot tubs, making it an appealing choice for travellers seeking relaxation and comfort. This vibrant neighbourhood is known for its lively mix of shops, trendy restaurants, and lively arts scene, providing plenty of entertainment options nearby.
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.
Are there pet-friendly holiday rentals in Wicker Park?
In Wicker Park, there are several pet-friendly holiday rentals available, making it an excellent choice for travellers who want to bring their furry companions along. This trendy neighbourhood is well-known for its vibrant atmosphere, featuring a mix of residential charm and urban conveniences. Many of the rentals in the area come equipped with modern amenities such as fully stocked kitchens, spacious living areas, and sometimes outdoor spaces like private patios or balconies, which can be particularly enjoyable for pets.
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 most popular time to visit Wicker Park is during the vibrant summer months, particularly from May to July. This peak season draws in visitors eager to immerse themselves in the energetic atmosphere of the neighbourhood, filled with lively street festivals, outdoor dining, and a bustling arts scene. July, in particular, showcases the area's charm, with warm temperatures averaging in the low 20s Celsius, making it ideal for sightseeing and enjoying the abundance of nearby parks and local attractions.

If you prefer a quieter experience, consider travelling in December. Although it's the low season, this month brings a unique charm, as Wicker Park is beautifully adorned with festive decorations. You can enjoy the local shops and cafés at a leisurely pace, great for those seeking a more relaxed holiday rental experience.
Are there any remote work holiday rentals in Wicker Park?
In Wicker Park, Illinois, there are around 16 holiday rentals specifically suited for remote work, making it an excellent choice for those looking to combine work and leisure. These accommodations typically offer dedicated workspaces, including desks and ergonomic chairs, ensuring comfort during extended periods of productivity. Many properties also come equipped with high-speed Wi-Fi and computer monitors, suiting the needs of remote professionals. 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?
Wicker Park is a vibrant neighbourhood known for its artistic flair and dynamic atmosphere, making it a popular destination for visitors. The area's main attraction is Wicker Park itself, a spacious green space featuring walking trails, a pond, and sports facilities, superb for leisurely strolls or picnics. The neighbourhood is also renowned for its independent boutiques, trendy cafes, and diverse dining options, particularly along Milwaukee Avenue and Damen Avenue.
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 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 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.

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