Wicker Park holiday lettings

We found 1,325 holiday rentals — enter your dates for availability

Discover a selection of 18 homes, 37 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:29 May - 5 Jun

Image gallery for Gilded Age Gold Coast Mansion with Parking, Deck, Fireplaces

Interior
9.6 out of 10, Exceptional, (7 reviews)
Exceptional
(7 reviews)

Gilded Age Gold Coast Mansion with Parking, Deck, Fireplaces

Chicago

7% off
Price is £12,420
for 7 nights, 1 home
£1,774 per night
includes taxes & fees
Gilded Age Gold Coast Mansion with Parking, Deck, Fireplaces

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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 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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