15 Best Things to Do in Wicker Park, Chicago

Wicker Park, IL
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Wicker Park is a small and affluent neighborhood in Chicago, Illinois, that effortlessly blends culture and modernity.

Here, visual art, cuisine, music, and fashion come together to create a bustling community that celebrates human prowess and creativity.

It’s often called one of the most hipster places in the country, with quaint dive bars, numerous art galleries, vintage clothing stores, and other hallmarks of counterculture and progressivism.

So for those who are looking for a unique, multifaceted destination that will appeal to all your senses, this place is the best destination to be.

Visit this unusual and excellent neighborhood on your next weekend getaway!

Here are the 15 best things to do in Wicker Park:

Explore the Outdoors at The 606

View of The 606
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On what was once an abandoned rail line now stands The 606, a multi-use recreational path that spans 2.7 miles.

This Chicago attraction passes right through Wicker Park on Bloomingdale Avenue, and it will bring you to some of the most significant landmarks in this part of the city.

In fact, this green space is a living work of art in itself, with painted murals, architectural marvels, and lots of open spaces where the community gathers.

View of The 606
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Many events take place along the path, such as fun runs, bake-offs, concerts, art workshops, and yoga classes—all of which you’re welcome to join in.

But if you don’t see any during your visit, it’s also just fine to explore the trail as it is.

You’d be brought to other neighborhoods like Humboldt Park, West Town, and Logan Square, which also have their own unique attractions.

View of The 606
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Shop Vintage Apparel at Kokorokoko

Don’t be intimidated by the unusual name—Kokorokoko is actually a well-loved vintage clothing shop that is a must-visit for thrift haulers.

It’s one of the many vintage fashion stores in the area, but this attraction takes the cake as the most visited among the rest.

And for a good reason.

Stepping into the store feels like going into a boutique fashion outlet in New York, owing to chic interior design, natural lighting, and a clean layout that’s refreshing to the eyes.

You’d find a lot of 80s and 90s clothing along the shelves and racks, from denim jackets, parachute pants, printed shirts, sequined hats, and neon dresses.

Just be patient during your search, and you might find something that will bring your fondest memories of the 90s.

Play and Drink at Emporium Wicker Park

Many attractions in town will bring you back in time, and one of the most famous ones is Emporium Wicker Park.

This place combines old-school and contemporary arcade games with whiskey and craft beer, making it a fun place for those who need to get away from the stress of city life.

Once you enter, you’d be immediately hit by the tavern ambiance, with the neon lights, industrial design, and busy atmosphere.

You’d find pool tables, pinball machines, foosball tables, and so many other games that will bring out a feeling of nostalgia.

While playing, enjoy the very best beers, ales, and other refreshing alcoholic beverages that are manufactured right in the building.

There are also live shows and music events to watch out for, and they definitely add another level of fun to your visit.

Emporium Wicker Park truly is the best place to warm up for the other destinations waiting.

Immerse in the Retro Vibe of Dove’s Luncheonette

Dove’s Luncheonette is another crowd-favorite dining establishment because of the retro decor reminiscent of Chicago’s bygone years.

It’s also part of the award-winning One Off Hospitality Group, which has other establishments in Chicago.

Under their management, Dove’s Luncheonette has emerged as a well-known restaurant that offers Tex-Mex dishes.

Their menu consists of tamales, relleños, salads, and burgers, all made from fresh and quality ingredients.

The restaurant is also famous for its delicious selection of cocktails, beers, and other beverages inspired by Southern cuisine.

Visit the Dive Bars Along Milwaukee Avenue

View of Milwaukee Avenue
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While many people debate the qualities that make a dive bar a dive bar, there’s one thing that they can all agree on: it’s a hipster haven.

In general, dive bars are small and eclectic establishments that offer an authentic and unpretentious ambiance.

And there are a lot of them here in Wicker Park, especially along Milwaukee Avenue.

View of Milwaukee Avenue
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Phyllis Musical Inn is one of the more visited ones because of their beer garden, and they also regularly hold live concerts in their relaxed saloon setting.

At Whiskey Business, you can enjoy cocktails, beers, and other refreshing beverages while on their scenic and colorful roof deck.

Nick’s Beer Garden has pool tables and jukeboxes aside from their tasty drinks, allowing you to entertain yourself while you sip your favorite beverage.

Check Out the Paintings at Flat Iron Building

The US has a fair amount of these so-called “Flat Iron Buildings,” which are triangular structures located usually at the intersection of three roads.

Wicker Park is no exception, boasting its own Flat Iron Building that has been around since the 1920s.

And since the 1980s, it has been turned into an artist’s colony.

It’s one of the well-known hubs for visual and performance art in the neighborhood, with more than 40 artist studios, a tattoo parlor, a theater, and other facilities.

Everyone is welcome to explore the building and see the various works of art on display.

But the real treat is the special events that happen every first Friday of the Month.

Flat Iron Building opens its doors to the Wicker Park community so they can share their work, leading to a flurry of paintings, sculptures, and other beautiful pieces.

The event is usually accompanied by musical performances and other entertaining shows that elevate the whole experience.

Join the Crowds at The Hideout

Nothing screams “counterculture” as a small, clandestine performance venue that may or may not have started as an illegal establishment.

The Hideout did begin as a balloon-frame house, built in two days in order to avoid the authorities who might come and take it down.

And today, it still stands.

It even earned a reputation as one of Chicago’s most beloved small venues, attracting a diverse crowd that wants to immerse in the hipster culture.

Considered as the house of rebels, this place hosts performances of many budding indie bands in genres like punk rock, indie rock, and alt-country.

And you can enjoy these performances while chugging mugs of beer or eating hearty Chicago staples.

It’s really the best destination for those who do not seem to fit in in our polite and sensitive society.

Laugh Your Worries Away at The Comedy Clubhouse

For those who are looking for a good laugh, The Comedy Clubhouse is the place to be.

It’s actually the top-rated club of its kind in the whole of Chicago, attracting throngs of people every showing for some good entertainment.

Their lineup of comedians will tickle the laugh out of you with improvs, stand-up, and scripted performances.

In fact, some of them have become stars in shows like Parks and Recreation, the Office, and The Mindy Project.

So you can expect hilarious skits and theatrical acts that will have you rolling on the floor.

Best of all, you can enjoy the shows along with delicious drinks and refreshing alcoholic drinks.

Enjoy a Family Day at Wicker Park

People at Wicker Park
Adam Jones, Ph.D., CC BY-SA 3.0, via Wikimedia Commons

Not to be confused with the neighborhood itself, Wicker Park is the main outdoor destination within this area.

It’s quite small, covering only 4.74 acres, but it’s an excellent destination nonetheless with its many modern amenities, well-tended gardens, and other facilities.

And who doesn’t love a gorgeous green space that serves as a respite from urbanity?

The beautiful fountain right in the middle, framed by trees and lush flowering plants, creates a peaceful ambiance for those who want a relaxing afternoon.

If you want to bond with your loved ones, there are other spaces for activities like picnics and outdoor sports.

There are even annual and seasonal events that you should watch out for, such as movie screenings, farmers markets, and live concerts by local performers.

Most of the community comes together to celebrate these activities, giving you a chance to mingle with locals and immerse in their culture.

Shop for Stylish Apparel in the Many Boutiques Around Town

Wicker Park stands as a vanguard of fashion in this region of the US, so you definitely shouldn’t miss the many boutiques dotting every corner.

There’s something for every taste and preference in the curated shelves of these shops, making Wicker Park a fashionista’s heaven.

Penelope’s is a cozy nook offering trendy items from US and European fashion brands, with casual apparel and glamorous accessories gracing their displays.

At Ragstock, you’d find hip pieces that are an equal mix of new and vintage—a great spot for someone looking for one-of-a-kind clothing.

For those who want stylish men’s clothing, Mildblend Supply Co. has a collection of fine leather goods, denim jeans, rugged footwear, and more!

Buffalo Exchange is where you can trade or sell your own vintage clothing, and you can also find hip and trendy apparel within their store.

Catch a Show at The Den Theatre

Sitting across Emporium Wicker Park is a local performance art venue favored by locals and visitors alike.

The Den Theatre is more spacious than other facilities of its kind in the neighborhood, seating more than 200 people at a time.

As one of the places where artistic expression and creativity are encouraged, this place holds performances that provoke minds and challenge the existing culture.

So while here, you can expect plays, live music concerts, and other shows that champion diversity, inclusivity, and change.

It’s not hipster if it’s not counterculture, after all.

So check out their calendar today and see their upcoming shows.

That way, you can schedule your itinerary around a performance that you want to see.

Try Exquisite Drinks at The Wormhole Coffee

Another marker of the 80s culture in Wicker Park is The Wormhole Coffee, a well-known establishment in the neighborhood.

There’s even a DeLorean inside, as well as posters of Ghost Busters, Indiana Jones, and other iconic 80s hits.

But most people come here for the aromatic coffees roasted and brewed in-house.

With these delicious drinks and the cozy, welcoming ambiance of the establishment, you’re guaranteed a great coffee-drinking experience.

The 80s theme is just icing on the cake.

Find Rare Music at Reckless Records

Inside View of Reckless Records
swimfinfan from Chicago, CC BY-SA 2.0, via Wikimedia Commons

Music lovers will have an exhilarating time exploring this well-known and historical attraction.

Reckless Records is an old-school music store that fits well with the hipster vibe of Wicker Park.

Whether you’re looking for previously owned LPs by an indie artist, a vinyl record by an underground 80s band, or DVD copies of a 90s blockbuster, they have it here.

Whatever genre, whatever period, and whatever type of media, they have it in their large and spacious store.

You can spend hours browsing the catalog looking for some rare items or a new artist to discover.

Their diverse and beautiful collection is arguably one of the largest in the state and the region, so it’s no wonder that this place has become an institution in Wicker Park.

Browse the Numerous Art Galleries

Hipster culture is almost synonymous with art, so it’s a guarantee that Wicker Park has many art galleries that embody this movement.

Aside from the ones in Flat Iron Building, there are many art hubs scattered along the streets and hidden within nondescript buildings in town.

Dreambox is one of these galleries featuring contemporary art by emerging and established local artists.

For those looking for something more cutting-edge or avant-garde, Johalla Projects is a large space that features art in various themes and media.

The Vertical Gallery, on the other hand, is focused more on urban and street art, showcasing graffiti works and graphic designs that are simply stunning.

LVL3 is an artist-run exhibition space specializing in up-and-coming local artists, allowing them to show off their works to a more mainstream crowd.

Sample Mexican Dishes at Big Star

Set in the heart of Wicker Park, Big Star is one of the most visited restaurants in the city.

It prides itself as a “bourbon and beer-focused” dining establishment that offers authentic Mexican dishes.

The Wild West vibes of this restaurant add to the appeal, with themed decor, dishes, and entertainment that really elevates your dining experience.

Try some of their savory burritos, tasty nachos, and cheesy quesadillas.

There are also stranger dishes for those with adventurous tastebuds, such as tacos of exceedingly exotic flavors, fresh ensaladas, and crispy flautas.

Of course, don’t forget to try their drinks, ranging from agave spirits, whiskeys, cervecas, and craft beer.

There’s also occasional live music by talented bands to entertain you while you dine al fresco at their patio.

Final Thoughts

As a hotspot for music, art, fashion, and food, Wicker Park has lots of attractions in store.

You don’t need to be a hipster to enjoy all these wonders.

So reference this list and plan your itinerary for an amazing and memorable trip!