Photo by Chandan Rastogi

Wicker Park holiday lettings

We found 1,350 holiday rentals — enter your dates for availability

Discover a selection of 18 homes, 34 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:3 Oct - 10 Oct
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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.

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.

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

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.

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 accommodation in Wicker Park?
Apartments are the most popular kind of holiday rental in Wicker Park, according to our data. Even if you have something bigger or smaller in mind, Vrbo has properties in a variety of shapes and sizes. Compare our options to find your ideal fit.
How much does it cost to rent a holiday rental in Wicker Park?
Season, length of stay and property type are among the factors that can influence the price of a holiday home. Simply add your travel dates to find your perfect match. From cosy country cottages to expansive villas, all Vrbo holiday rentals offer unbeatable value.
How much does it cost to rent a beach house in Wicker Park?
The average price for a holiday home by the beach in Wicker Park depends on when you're travelling and the size and style of property you're searching for. You can easily and quickly find prices on Vrbo by entering your dates of travel. Then make use of the filter tool to choose the number of bedrooms and amenities that you prefer, such as WiFi, air conditioning and a hot tub.
Are there pet-friendly holiday rentals in Wicker Park?
You're in luck. There are. You'll have your pick of 28 stays that allow pets in Wicker Park on Vrbo. Our furry companions also deserve a little time out, so simply use our search function for pet-friendly holiday rentals to find a perfect pad where your doggie can be near his favourite humans.
What are popular rental amenities in Wicker Park?
Nearby museums, a barbecue grill and a firepit rank as the most popular rental amenities in Wicker Park. Whether you're travelling as a party of one, with your significant other or a bunch of friends, Vrbo can help you find a holiday home that matches your style with all the extras you're looking for.
Are there large group holiday rentals in Wicker Park?
Pick from three properties in Wicker Park that can accommodate 10 or more people. Whether you're organising time away with the family or a special event like a birthday party, there's plenty of space to get your group together under one roof.
Are there holiday rentals in Wicker Park that welcome kids?
With 27 family-friendly holiday properties to choose from in Wicker Park, now is a fantastic time to introduce the kiddos to the magic of travel. Click on our "Properties good for families" filter to browse stays that feature conveniences perfect for holidaying families, such as extra bedrooms, pools, entertainment units and bunk beds.
What are the top attractions for families in Wicker Park?
There are plenty of fabulous things to do and see with the family in Wicker Park, including:

  • Navy Pier
  • Chicago Riverwalk
  • Shedd Aquarium

Are there one-bedroom holiday rentals in Wicker Park?
Yes, Wicker Park has eight one-bedroom rentals on offer. Often positioned in prime areas thanks to their smaller size, a one-bedroom rental is great if you're getting away with your partner or a pal. And with comforts such as laundry facilities and more privacy than a standard hotel, you'll be able to kick back while enjoying this top destination.
Can I find two-bedroom holiday rentals in Wicker Park?
Wicker Park has five two-bedroom holiday properties for you to pick from. Enjoy a holiday home with all the comfort and privacy you want at a fantastic price on Vrbo.
Are there holiday rentals with WiFi in Wicker Park?
Wicker Park has 12 holiday rentals with WiFi, so you can stay connected while travelling. Simply check the "WiFi" box in our handy search filter for a list of properties with this feature. From streaming movies with your family to writing and sending emails, these Vrbo homes make it a cinch to get online.
How can I find holiday rentals with air conditioning in Wicker Park?
Select your travel dates and then use the filters to locate holiday rentals with ac in Wicker Park on Vrbo. With 24 air-conditioned properties to choose from here, you can look forward to a cool and comfortable stay.
How old do you have to be to rent a holiday rental in Wicker Park?
You'll need to check with the Wicker Park holiday property you want on Vrbo as the minimum age differs. However, normally it's 16, 18 or 21.
How long can I rent a holiday rental in Wicker Park for?
The length of time you can rent a holiday rental in Wicker Park varies according to the property. Just enter your chosen dates to display a list of options offering extended stays. With loads of creature comforts like washing machines and air conditioning, as well as some offering weekly or monthly discounted prices, you're sure to get someplace just right to call your home away from home in Wicker Park.

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