Wicker Park is one of Chicago’s most popular neighborhoods, known for its trendy boutiques, hip restaurants, and vibrant nightlife. Whether you’re a visitor or a local, there’s something for everyone to enjoy in Wicker Park.
In this blog post, we’ll share 21 of the best things to do in Wicker Park, Chicago. From shopping and dining to exploring art galleries and catching live music, this list has something for everyone.
Best Things to Do in Wicker Park, Chicago: A Comprehensive Guide
You’re going to love Chicago’s Wicker Park, a vibrant neighborhood located on the west side of the city.
This historic neighborhood, home to one of the first skyscrapers built in the city (the Northwest Tower, now the Robey Hotel), is known for its eclectic charm, thriving arts scene, and diverse culinary offerings.
Wicker Park truly offers a captivating experience for both locals and visitors alike. There is lot going on in this neighborhood: every time I visit, I discover something new that captures my attention. It’s one reason why it’s one of my favorite neighborhoods in Chicago.
From the delicious smells coming from Stan’s Donuts on the corner of Damen and North to the hustle and bustle of Milwaukee Avenue, Wicker Park has something for everyone.
In this fun guide, we’ll share the neighborhood’s rich history, highlight why it’s a great place to visit, showcase the best things to do, recommend mouthwatering places to eat and drink, suggest comfortable places to stay, and unveil the most enticing points of interest.
Get ready to immerse yourself in the vibrant tapestry of Wicker Park!
Located about 15 minutes northwest of downtown Chicago, use this Chicago Neighborhood Guide to plan your trip to one of the most vibrant neighborhoods in the city of Chicago.
History of Wicker Park, Chicago
Wicker Park’s history dates back to the 1870’s, when it was originally established as a fashionable residential district.
Over the years, the neighborhood has transformed into a cultural haven, attracting artists, musicians, and creative minds. The name “Wicker Park” originates from the beautiful park located at the heart of the neighborhood, offering a serene green space for residents and visitors alike.
Today, Wicker Park maintains its independent spirit and artistic vibe, with preserved landmarks such as the historic Flat Iron building, Northwest Tower, the North Avenue Bridge and St. Mary’s of the Angels Church.
Why Wicker Park is a Great Place to Visit
Chicago’s Wicker Park is a haven for creative souls that combines artistic flair, vibrant energy, and a sense of community. Whether you’re a local looking for a lively weekend or a visitor exploring the city, Wicker Park promises an unforgettable journey.
With its thriving arts scene, diverse culinary options, and exciting events, Wicker Park captures the essence of Chicago’s eclectic culture.
Best Things to Do in Wicker Park
Explore the Bloomingdale Trail – 1801 N Ridgeway Ave
Immerse yourself in the lush greenery of the Bloomingdale Trail, an elevated park that offers a unique perspective of Wicker Park and its surroundings. Take a leisurely walk or bike ride along this former railway line and enjoy stunning views of the city.
Take a Dip in the Cabana Club – 2018 W North Ave Chicago, IL 60647
Located at the iconic Hotel Robey, this may be the only public outdoor swimming pool in the city. Open seasonally from May to September, you can enjoy drinks poolside from the rooftop. The pool is not big, but it’s definitely enough to cool off while taking in some amazing views in the summertime.
Visit Wicker Park Farmers Market – 1425 N Damen Ave
Experience the vibrant local community and support sustainable travel practices by visiting the Wicker Park Farmers Market. Discover a wide variety of fresh produce, artisanal products, and locally made goods.
Unleash Your Inner Gamer at Emporium Wicker Park Arcade Bar -1366 N Milwaukee Ave
Dive into a world of arcade games and nostalgia at Emporium Arcade Bar. Challenge your friends to classic and modern arcade games while enjoying a wide selection of craft beers and cocktails.
Embrace the Artistic Vibe of the Flat Iron Arts Building – 1579 N Milwaukee Ave
Explore the creative energy of Wicker Park by visiting the Flat Iron Arts Building. This historic landmark houses numerous artist studios, galleries, and creative spaces. Take a stroll through the building and immerse yourself in the neighborhood’s vibrant art scene.
Explore the Street Art Scene
Wicker Park is a haven for street art lovers. Take a leisurely stroll through theneighborhood and marvel at the vibrant murals and graffiti adorning the walls. Each piece tells a unique story and adds to the artistic fabric of the community.
Attend the Renegade Craft Fair
If you’re visiting at the right time, don’t miss the Renegade Craft Fair. This lively event showcases the works of talented artists and makers from around the country, offering a unique opportunity to support independent artisans and find one-of-a-kind treasures.
Head to the Comedy Clubhouse – 1462 N Ashland Ave
Immerse Yourself in the Local Comedy Scene for an evening of laughter and entertainment. This intimate comedy venue hosts a variety of shows featuring local comedians, providing an unforgettable night out.
Indulge in Delicious Ice Cream Treats
Cool down with a visit to local ice cream shops in Wicker Park. Whether you choose to enjoy a scoop at Jeni’s Splendid Ice Creams – 1505 N Milwaukee Ave, or sample the inventive flavors at Black Dog Gelato – 859 N Damen Ave, these spots will satisfy your sweet tooth.
Discover Hidden Gems at Mildblend Supply Co. – 1342 N Milwaukee Ave
Explore this trendy boutique that offers a curated selection of high-quality denim, clothing, and accessories. Find your perfect style while immersing yourself in the fashion scene of Wicker Park.
Enjoy the Blue Line Art Scene
Hop on the Blue Line, Chicago’s iconic subway line, and explore the diverse art installations that adorn several stations along the way. From intricate murals to thought-provoking sculptures, the Blue Line transforms the daily commute into a visual delight.
Visit the Iconic Smoke Daddy – 1804 W Division St
Experience the flavors of authentic barbecue at Smoke Daddy, a popular spot known for its mouthwatering smoked meats, live music, and lively atmosphere. Indulge in delicious ribs, pulled pork, and homemade sauces while enjoying the vibrant energy of the neighborhood.
Head to Wicker Park Fest
This annual event has been called “Chicago’s Best Street Festival of the Summer,” and that’s saying something for a city that prides itself on amazing street fests all summer long. Live music, amazing food and lots of fun – don’t miss it.
Catch a Show at The Den Theatre – 1333 N Milwaukee Ave
Immerse yourself in Chicago’s performing arts scene at The Den Theatre. This vibrant venue hosts a variety of innovative performances, including plays, musicals, and more.
Best Shopping in Wicker Park
Take a stroll along Milwaukee Avenue, the vibrant heart of Wicker Park. Discover an array of unique shops, stylish boutiques, vintage clothing stores, and secondhand shops that offer a glimpse into the neighborhood’s eclectic charm. You’ll find a huge mix of national brands like Doc Martens, North Face, Urban Outfitters, Free People, Yeti and Lululemon as well as many independently owned shops and boutiques. There are a lot of vintage and secondhand stores to check out, too. Here are few of our favorites:
Buffalo Exchange – 1478 N Milwaukee Ave, Chicago, Illinois 60622
You’ll find a good mix of new and used clothing that you can buy, sell, or trade on the spot at this popular spot.
Ragstock – 1459 N Milwaukee Ave, Chicago, IL 60622
You’ll find a mix of new and vintage clothes here: it’s a must when you’re on the hunt for the perfect ugly Christmas sweater for your holiday together.
Adidas Original Flagship Store- 1532 N Milwaukee Ave, Chicago, IL 60622
If you’re a fan of sneakers, this is the place for you. The flagship store for Adidas, you’ll find everything from apparel to vintage shoe styles. This sprawling Adidas store features shoes and clothing by this world-renowned athletic shoe brand.
Belmont Army – 1318 N Milwaukee Ave, Chicago, IL 60622
Conveniently located within walking distance of the Division or Damen Blue Line stops, you’ll find vintage clothing in this army surplus store stocking men’s and women’s apparel. Even if you’re not in the market for army-surplus-style fashion, it’s a fun place to check out.
Akira – 1814 W North Ave, Chicago, IL 60622
This local chain offers trendy women’s clothes and accessories at a good price; you can pick up some unique items here.
Saint Alfred – 1529 N Milwaukee Ave, Chicago, IL 60622
This upscale streetwear shop in Wicker Park is the pace to be for the latest sneaker drops. Good selection of footwear, hats, and shirts, too.
John Fluevog Shoes – 1551 N Milwaukee Ave, Chicago, IL 60622
You’ll find beautifully made shoes from this Canada-based shoemaker whose brightly colored designs have attracted the likes of singer Jack White of the White Stripes, and clothing designed Anna Sui.
DECIEM The Abnormal Beauty Company – 1401 N Milwaukee Ave, Chicago, IL 60622
One of my favorite stores in the city is this health and beauty store that focuses on clean skin care. They carry a full line of The Ordinary, a top skincare brand.
The Red Balloon – 1940 N Damen Ave, Chicago, IL 60647
One of the best children’s stores in the city, you’ll find everything from toys and games to clothing, gifts, and more. Ther are tons of cute stuffed animals that you won’t find anywhere else!
Myopic Books – 1564 N Milwaukee Ave, Chicago, IL 60622
If you’re a book lover, Myopic Books should be at the top of your bucket list. There’s more than 70,000 books in this amazing Chicago bookstore on Milwaukee Avenue with three levels to peruse. In addition to an amazing collection, they also host book signings, concerts and poetry nights.
Reckless Records – 1379 N Milwaukee Ave
Vinyl enthusiasts shouldn’t miss a visit to Reckless Records, a beloved record store that offers an extensive collection of music from various genres. Spend hours digging through crates and uncover hidden gems to add to your collection.
Places to Eat and Drink in Wicker Park
You’ll find a variety of new hotspots and old favorites in Wicker Park. Here are a few of our favorite stops:
The Violet Hour – 1520 N Damen Ave
Step into a world of craft cocktails at The Violet Hour. Known for its elegant ambiance and innovative drinks, this speakeasy-style cocktail bar offers an unforgettable experience.
Café Robey – 2018 W North Ave
Indulge in a delicious meal at Café Robey, located in The Robey Hotel. This stylish restaurant offers a range of culinary delights, from delectable brunch options to creative dinner plates.
Antique Taco – 1360 N Milwaukee Ave
Savor the flavors of Mexican cuisine with a modern twist at Antique Taco. This popular eatery serves up mouthwatering tacos made with fresh ingredients and unique flavor combinations.
Doves Luncheonette – 1545 N Damen Ave
Visit Doves Luncheonette for a cozy dining experience featuring American comfort food. From savory sandwiches to delectable brunch items, Doves Luncheonette has something for everyone.
Takito Kirchen- 2013 W Division St, Chicago, IL 60622
From artisanal street tacos to handcrafted margaritas, you’ll find a wide range of gluten-free menu items to choose from, all featuring a fresh Mex taste.
Wormhole Coffee – 1462 N Milwaukee Ave, Chicago, IL 60622
A DeLorean in a coffee shop? Yep, and that’s not all you’ll find at this 80’s themed coffee shop that ‘s a favorite with coffee lovers in Chicago. They pour coffee from locally roasted beans, and you can enjoy your cup in their comfy shop while surrounded by endless memorabilia.
Piece Brewery – 1927 W North Ave, Chicago, IL 60622
Looking for the best pizza in Wicker Park? It’s got to be here, at this cozy brewery on North Ave. I was here when it opened up and was amazed by the flavors in my slice; it’s only gotten better since.
Lone Owl Gastropub- 1547 N Milwaukee Ave, Chicago, IL 60622
You can’t miss this fun, dog-friendly eatery on Wicker Park- look for the shining red phone booth out front! You’ll find a Pacific Northwest vibe with lots of unique and tasty seafood, as well as craft beer and cocktails.
Places to Stay in Wicker Park
The Robey Hotel – 2018 W North Ave
Immerse yourself in modern luxury at The Robey Hotel. This trendy boutique hotel offers stylish rooms, a rooftop lounge with panoramic views of the city, and easy access to Wicker Park’s attractions.
Urban Holiday Lofts – 2014 W Wabansia Ave
Experience affordable accommodations at Urban Holiday Lofts, a vibrant hostel offering shared and private rooms. Socialize in the communal kitchen and common areas while enjoying the neighborhood’s lively atmosphere.
More About Wicker Park in Chicago IL
As you explore the vibrant neighborhood of Wicker Park, be sure to soak in the lively atmosphere, indulge in delicious food and drink, and embrace the creative spirit that permeates the streets. Wicker Park and its surrounding areas offer a blend of diverse attractions, making it a must-visit destination within Chicago’s vibrant neighborhoods.
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