Wicker Park vacation rentals

We found 1,283 vacation rentals — enter your dates for availability

Discover a selection of 21 homes, 31 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:Jul 3 - Jul 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, (184 reviews)
Exceptional
(184 reviews)

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

Chicago

17% off
Price is $720
$5,040 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.

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, apartments, and condos are all popular rental options, with several of each type available throughout this vibrant neighborhood. Many of these rentals are situated close to local attractions, including trendy shops, art galleries, and a variety of dining options. Travelers can expect amenities such as fully equipped kitchens, modern living spaces, and in some cases, private outdoor areas or balconies that provide a great spot to relax after exploring the lively surroundings.
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 vacation rental amenities include fully equipped kitchens, which allow travelers to prepare their own meals and enjoy the convenience of home cooking. Many rentals also feature balconies, providing a lovely outdoor space to relax and take in the neighborhood's vibrant setting. For those needing to work or study during their stay, desks and desk chairs are commonly available, making it easy to maintain productivity. Additionally, onsite parking is a sought-after amenity, particularly in this bustling area where street parking can be limited.
Can I find family house rentals in Wicker Park?
In Wicker Park, Illinois, there are several family house rentals available, making it a great choice for those traveling with kids. This vibrant neighborhood is known for its lively atmosphere, featuring a mix of trendy shops, parks, and family-friendly eateries. Many of the homes offer spacious living areas, full kitchens for preparing meals, and outdoor spaces where children can safely play.

Nearby, visitors can explore parks like Wicker Park itself, which has playgrounds, sports facilities, and walking paths, providing ample opportunities for family activities. Additionally, the area is rich in cultural attractions, including art galleries and music venues, which can be enjoyed by the whole family.
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 pools or hot tubs, making it an appealing option for travelers looking to unwind. This trendy neighborhood in Chicago is known for its vibrant arts scene, energetic shops, and diverse dining options. Many of the rentals provide modern amenities such as private hot tubs, relaxing outdoor spaces, and fully equipped kitchens, great for both comfort and entertaining.
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.
Can I book pet-friendly vacation rentals in Wicker Park?
In Wicker Park, travelers will find several pet-friendly vacation rentals that cater to those looking to enjoy this vibrant neighborhood. Many of these properties feature modern amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces like balconies or patios, superb for relaxing after a day of exploration.

Wicker Park is known for its artistic vibe, trendy shops, and diverse dining options, making it an exciting place to stay. Additionally, the neighborhood has nearby parks like Wicker Park itself, which offers walking paths, green space, and a dog-friendly atmosphere, allowing pets to enjoy the outdoors.
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?
The best time to visit Wicker Park for a vacation rental is during the peak season from May to July, with July being the most popular month. This vibrant neighborhood comes alive in the summer, offering an array of outdoor activities, festivals, and a lively option that attracts travelers seeking both adventure and cultural experiences.

During these months, Wicker Park boasts pleasant temperatures ranging from the mid-60s to the mid-80s Fahrenheit, making it ideal for exploring local parks, enjoying al fresco dining, or visiting the eclectic shops and art galleries that line the streets. With a variety of events, including street festivals and music performances, you can immerse yourself in the local culture while enjoying the warm summer weather.

For those looking for a more budget-friendly option, consider planning your visit in December. While this month may be quieter, it offers a unique charm with its festive decorations and cozy ambiance, making it a lovely time to explore the neighborhood's coffee shops and boutiques without the summer crowds.
Are there any remote work vacation rentals in Wicker Park?
In Wicker Park, Illinois, there are about 10 vacation rentals that cater specifically to remote work needs. This vibrant neighborhood is known for its lively mix of shops, restaurants, and cultural venues, making it a lively place for both work and leisure. Travelers can expect amenities such as high-speed Wi-Fi, dedicated workspaces with desks and chairs, and comfortable living areas conducive to productivity. Many properties also feature full kitchens, allowing for convenient meal preparation during longer stays.

Wicker Park is home to picturesque parks and a thriving arts scene, providing opportunities for relaxation and inspiration outside of work hours. 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, Illinois, United States of America?
In Wicker Park, visitors can enjoy a vibrant mix of attractions that reflect the neighborhood's artistic and cultural spirit. The Wicker Park itself is a major highlight, featuring beautiful green spaces, walking paths, and a playground, making it an ideal spot for relaxation or outdoor activities. The park often hosts community events, art fairs, and festivals throughout the year.

Nearby, the neighborhood is known for its eclectic mix of boutiques, vintage shops, and local galleries that showcase the work of emerging artists. The area is also home to numerous acclaimed restaurants and cafes, offering a diverse culinary scene that ranges from casual eateries to fine dining options.

For those interested in nightlife, Wicker Park boasts a variety of bars and music venues, including places that feature live music and DJ sets, contributing to the neighborhood's lively option. Additionally, the historic Damen Avenue and Milwaukee Avenue intersections are bustling hubs for shopping and entertainment, with plenty of public art installations adding to the area's charm.
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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