Wicker Park vacation rentals

We found 1,339 vacation rentals — enter your dates for availability

Discover a selection of 17 homes, 34 apartments, and other vacation rentals in Wicker Park that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, vacation homes have the amenities you need and want for your stay, which might include WiFi and a hot tub. No matter what you're looking for, you'll be able to choose a rental for everyone's needs, including a place that is accessible or non-smoking.

Vacation rentals with weekly discounts - Wicker Park

Showing deals for:Apr 3 - Apr 10

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

Living area
9.8 out of 10, Exceptional, (183 reviews)
Exceptional
(183 reviews)

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

Chicago

17% off
Price is $489
$3,424 for 7 nights
All fees included
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24

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Find out more about Wicker Park

Why visit Wicker Park

  • Cultural Hub: Immerse yourself in Wicker Park's vibrant arts scene, featuring galleries, theaters, and live music venues.
  • Eclectic Shopping: Discover unique boutiques and vintage shops that offer a one-of-a-kind shopping experience.
  • Charming Cafes: Enjoy a leisurely coffee or meal at cozy cafes that reflect the neighborhood's artistic vibe.
  • Scenic Parks: Relax in beautiful parks, perfect for picnics, strolls, or enjoying local events.
  • Convenient Location: Use Wicker Park as a base to easily explore downtown Chicago and its iconic attractions.

Popular types of accommodation around Wicker Park

If you're exploring Wicker Park for your next getaway, you're in for a treat. Our most popular types of vacation rentals include stylish apartments, cozy houses, and modern condos. Whether you're looking for apartments in Wicker Park, Cicero apartments, Oak Park apartments, or even downtown Chicago apartments, you’ll find the perfect spot to unwind and enjoy all that this vibrant neighborhood has to offer.

  • Apartments: The top choice for vacationers in Wicker Park, offering stylish living spaces for solo travelers or families.
  • Houses: A fantastic option for those seeking more space and comfort, perfect for groups or families wanting a home-like experience.
  • Condos: A popular selection for travelers who desire modern amenities and a convenient location in the heart of the neighborhood.
  • Cottages: Charming and cozy, these rentals provide a quaint getaway atmosphere for a peaceful retreat.**

Top attractions near Wicker Park

Wicker Park offers a fantastic vacation experience for families and urban adventurers alike, featuring a mix of skyscrapers, vibrant streets, and beautiful parks. This lively neighborhood is perfect for those seeking cultural experiences and city adventures, with a variety of attractions that cater to families and travelers looking to immerse themselves in the local vibe. Explore the unique charm of Wicker Park for a memorable getaway in Chicago.

  • Michigan Avenue: Known as the Magnificent Mile, this vibrant street is lined with upscale shops, restaurants, and iconic architecture, offering a quintessential Chicago experience.
  • Chicago Riverwalk: This scenic promenade along the Chicago River is perfect for families, featuring beautiful views, outdoor dining, and recreational activities like boat rentals.
  • Willis Tower: Once the tallest building in the world, this iconic skyscraper offers breathtaking views of the city from its Skydeck, where you can step onto glass ledges for a thrilling experience.

Things to do recommended for couples

Wicker Park offers delightful couple experiences. Enjoy live music at the Aragon Ballroom or House of Blues, both just a short drive away. For a cozy dinner, visit the Historic Michael Jordan Restaurant, where romance meets city charm. Create unforgettable memories together in this vibrant neighborhood.

Things to do recommended for families

Experience the thrill of Wrigley Field's sports atmosphere, unwind at Northerly Island Natural Area's serene surroundings, or enjoy wellness activities at The East Bank Club, all within a short distance from Wicker Park, perfect for family travelers seeking adventure and relaxation.

Things to do recommended for groups

Experience a night of culture and entertainment at the Vic Theatre, just 3 miles from Wicker Park. Enjoy laughter at Second City, located 2 miles away, perfect for family fun. For shopping enthusiasts, the Chicago Place Mall, also 3 miles away, offers a vibrant city atmosphere.

*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

If you're traveling with a group, family, bringing along pets, or planning an extended stay, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Wicker Park with a group: Think about how many bedrooms you'll require, as well as additional features like a full kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and many more on Vrbo.
  • Traveling to Wicker Park with young kids: Traveling with young kids can be quite demanding. It's important to prioritize their comfort and safety, along with having 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 families, a vacation isn't truly fulfilling without their furry companions by their side. If this resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly properties 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 searching for vacation rentals with special offers 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 features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Wicker Park

Wicker Park is a vibrant neighborhood in Chicago, perfect for families and urban explorers alike. Discover eclectic shops, charming cafes, and the lively arts scene that define this area. Just a short trip away, downtown Chicago offers iconic sights and bustling business vibes. Enjoy the friendly atmosphere and scenic parks, making Wicker Park an ideal base for your Chicago adventure.

  • Chicago: As a vibrant metropolis, Chicago is a cultural melting pot where Wicker Park is nestled. Visitors flock to this city for family-friendly activities, outdoor adventures, and urban experiences. Chicago offers an array of attractions, including bustling shopping areas, renowned sports facilities, and educational venues. Don't miss iconic landmarks such as the United Center and the famous Millennium Park, where outdoor concerts and art installations abound. With its diverse neighborhoods and rich history, Chicago is a great base for an unforgettable vacation.
  • Downtown Chicago: Located just 3 miles from Wicker Park, Downtown Chicago is the city's thriving core. This energetic neighborhood is perfect for families and outdoor enthusiasts alike, featuring a variety of shopping options, world-class theaters, and exciting arena entertainment. Key attractions include the Chicago Riverwalk, Grant Park, and the magnificent Art Institute of Chicago. Whether you're exploring the shops along the Magnificent Mile or enjoying a show at the Chicago Theatre, Downtown Chicago offers endless opportunities for adventure and cultural enrichment.
  • West Town: A mere 0.6 miles from Wicker Park, West Town is a dynamic neighborhood known for its artistic vibe and blossoming food scene. Families and outdoor lovers will enjoy the area's inviting urban parks and local music venues, while shopping enthusiasts can discover unique boutiques and artisanal shops. Highlights include the lively Humboldt Park and various theaters that host concerts and performances. With its close proximity to Wicker Park, West Town is an ideal spot to explore the creative spirit that defines Chicago.

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

Looking to save on your next trip? Consider being flexible with your travel dates, as this can lead to significant price differences. Also, extending your stay can often result in additional savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your entire booking. Being the planner truly pays off. By becoming a member of our travel rewards program, One Key, you'll gain access to exclusive discounts and earn OneKeyCash on eligible reservations. Join us today and begin enjoying your savings.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board provides a convenient platform for you to plan new trips, manage your existing plans, and review your bookings. Your saved or booked properties are neatly categorized into Potential, Upcoming, or Current Trips for easy access. To check out Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Wicker Park?
In Wicker Park, vacation houses are quite popular, with several available throughout the neighborhood. These properties typically offer spacious layouts, multiple bedrooms, and outdoor spaces, making them ideal for families or groups looking to enjoy the vibrant local culture and nearby parks. Additionally, apartments and condos are also prevalent, providing travelers with modern amenities such as fully equipped kitchens, comfortable living areas, and access to building facilities like gyms or rooftop terraces.
Are there any beach house rentals in Wicker Park?
In Wicker Park, Illinois, there are several beach house rentals available, offering travelers a great experience in this vibrant neighborhood. These rentals typically feature modern amenities, including fully equipped kitchens, spacious living areas, and outdoor spaces for relaxation. Many properties are situated near popular points of interest, such as the trendy shops and restaurants along Milwaukee Avenue and the scenic parks in the area.
How much does it cost to rent a vacation home in Wicker Park?
Prices for vacation 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 vacation 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 that often feature modern appliances like blenders and coffee/tea makers, providing convenience for travelers who prefer to prepare their own meals. Many rentals also come with kitchen islands, offering additional space for cooking and dining. Onsite parking is another sought-after amenity, making it easier for guests with vehicles to navigate the area.
Are there any family house rentals in Wicker Park?
In Wicker Park, Illinois, families can find around twelve vacation rentals that cater to their needs. This vibrant neighborhood is known for its artistic vibe and lively dining options, making it an exciting destination for visitors of all ages. Many of the homes here offer spacious living areas, fully equipped kitchens, and amenities like Wi-Fi and air conditioning, ensuring a comfortable stay.

Families can enjoy the nearby parks, such as Wicker Park itself, which features playgrounds, walking paths, and sports facilities. The area is also rich in local culture, with unique shops and family-friendly restaurants just a short stroll away.
Can I rent a vacation home with a pool or hot tub in Wicker Park?
In Wicker Park, there are several vacation homes available for rent that feature hot tubs, providing travelers with a comfortable and luxurious experience. This vibrant neighborhood in Chicago is known for its vibrant atmosphere, with a mix of trendy boutiques, art galleries, and lively dining options. Many of the rentals in this area come equipped with modern amenities, including spacious living areas, fully equipped kitchens, and private outdoor spaces that may also include patios or gardens.

Travelers can enjoy the convenience of being close to public transportation, making it easy to explore the greater Chicago area, while also having the option to unwind in the comfort of their rental after a day of adventure.
Are there any Wicker Park vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Wicker Park with parking available—perfect for families or travelers 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 vacation rentals in Wicker Park?
In Wicker Park, travelers can indeed find several pet-friendly vacation rentals that cater to both comfort and convenience. This vibrant neighborhood is known for its vibrant mix of shops, restaurants, and parks, making it an ideal spot for visitors with pets. Many vacation homes in the area come equipped with modern amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces where pets can enjoy the fresh air.

Wicker Park is home to the picturesque Wicker Park itself, which features walking paths and green spaces superb for leisurely strolls with your furry companions. The area also boasts numerous pet-friendly cafes and boutiques, ideal for those traveling with pets.
Can I find long-stay vacation rentals in Wicker Park?
A long-stay vacation rental in Wicker Park is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
When is the best time to visit Wicker Park for a vacation rental?
July is the most popular time to visit Wicker Park, where vibrant energy and a bustling atmosphere come alive. The peak season stretches from May through July, attracting travelers eager to explore the unique blend of art, culture, and dining that this trendy neighborhood has to offer. During these months, you'll find an abundance of outdoor festivals, street fairs, and open-air markets, creating an inviting environment for those who thrive on social experiences and outdoor activities.

The summer temperatures typically range from the mid-70s to low 90s Fahrenheit, providing superb conditions for leisurely strolls, bike rides, and enjoying the local parks. Wicker Park is known for its picturesque tree-lined streets and lively shops, making it an ideal setting for sightseeing and immersing yourself in the community's artistic vibe.

If you're looking for a more budget-friendly option, consider planning your visit in December. This month offers a charming winter atmosphere, where you can enjoy cozy cafes, local holiday markets, and festive decorations throughout the neighborhood.
Are there any remote work vacation rentals in Wicker Park?
In Wicker Park, Illinois, there are ample options for remote work vacation rentals, with around 15 available to cater to your needs. This vibrant neighborhood is known for its vibrant mix of shops, cafes, and lively arts scene, making it an ideal place for a workcation. Many rentals in this area come equipped with essential remote work amenities such as high-speed Wi-Fi, dedicated office spaces, and comfortable desk chairs. Some properties even feature additional conveniences like computer monitors to enhance productivity during your stay.

The neighborhood itself is rich with attractions, including parks, trendy restaurants, and cultural venues, offering plenty of opportunities to unwind after a day of work. Enjoy leisurely strolls through the charming streets, or take advantage of the nearby public transportation options to explore the broader Chicago area. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Wicker Park vacation rental?
Book your Wicker Park vacation 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 vacation 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 neighborhood known for its eclectic blend of culture, art, and entertainment. The centerpiece of the area is Wicker Park itself, a large green space ideal for picnics, outdoor activities, and community events. Surrounding the park, visitors can find a variety of trendy boutiques, cafes, and restaurants that reflect the neighborhood's creative spirit.

For art enthusiasts, the neighborhood boasts numerous galleries and street art, particularly along Milwaukee Avenue, which is lined with unique shops and eateries. The area is also home to the historic Double Door venue, known for live music, and the iconic Flat Iron Arts Building, which hosts art studios and exhibitions.

Additionally, Wicker Park's proximity to the Damen Blue Line station makes it easily accessible for visitors looking to explore the broader Chicago area.
Can I change or cancel my Wicker Park home rental booking on Vrbo?
To find Wicker Park vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 vacation 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.Vrbo also offers support via live chat through our Help Center, 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 organizing 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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