16 Fun Things to Do in Wicker Park (By a Local)

Wicker Park is a cool neighborhood located on the northwest side of Chicago that’s best known for being artsy and eclectic.

As a Chicago local, I can tell you firsthand that there are tons of incredible Chicago neighborhoods, but Wicker Park is easily one of my favorites.

In this article, I’ll be covering all the best things to do in Wicker Park including great restaurants, coffee shops, music venues, and secondhand shops.

You can reach Wicker Park by taking the Blue Line to Damen, where you’ll be dropped right into the bustling central hub, known as “Six Corners.”

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Best Things to Do in Wicker Park

Subterranean 

Enjoy live music at this local and intimate music venue.

📍 Google Maps | Phone: (773) 278-6600 | Subterranean Website | Hours: Showtimes vary | Tickets: $10 – $20+

If you’re looking for a cool, local, and intimate Chicago music venue, Subterranean in the center of Wicker Park is it. Subterranean has shows almost every night of the week, which makes it a great place to frequent if you love smaller shows and discovering new artists. 

Tickets and drinks are pretty affordable so this is a popular venue for music lovers in their 20s and 30s. I’ve discovered tons of new artists by attending shows here, and the energy is always so much fun. 

🛎️ Need a Hotel? The Robey is right across the street from Subterranean.

Chop Shop

Catch up-and-coming artists at this local music venue.

📍 Google Maps | Phone: (773) 537-4440 | Chop Shop Website | Hours: 11 am – 9 pm Wed-Sat, 11 am – 4 pm Sun, Closed Mon & Tue | Tickets: $20+ 

The Chop Shop is an eatery, bar, and music venue in the heart of Wicker Park.

People come here for delicious deli sandwiches and other American fare, however, the music venue is the big draw, which is located in the back of the 100-year-old former auto-shop building. 

The open and decked-out performance space brings in up-and-coming artists, as well as some bigger name artists. Shows here are a high-energy experience.

Myopic Books

Browse floor-to-ceiling shelves of used books.

📍 Google Maps | Phone: (773) 862-4882 | Myopic Books Website | Hours: 12 pm – 8 pm daily 

Carrying an impressive collection of over 60,000 used books, Myopic Books is a Chicago favorite and one of the city’s largest used bookstores.

Genres span from fiction and nonfiction to science and the arts. As soon as you walk in, you’ll be greeted with that familiar book smell. 

The bookstore itself has three floors, tons of smaller nooks, and sections for smaller genres. Although temporarily suspended, Myopic also hosts live music and reading events. For book lovers, this is a must-see if you’re visiting Wicker Park.

Thrifting on N Milwaukee Avenue

Spend hours browsing vintage clothing and secondhand goods.

📍 Google Maps | Phone: (773) 772-4296 | Hours vary for each store

The Wicker Park neighborhood is known for its local shops, and the vintage clothing and secondhand stores along N Milwaukee Avenue won’t disappoint.

Within one block is a huge roundup of thrift stores like store B vintage, Vintage Underground, Round Two, Ragstock, Crossroads Trading, Buffalo Exchange, and more. The stores range from curated vintage collections to typical thrift store finds and unique home goods. 

Thrifting in Wicker Park is a great way to spend the afternoon and is an especially popular activity for younger crowds. If you don’t have any luck thrifting, there are other popular stores nearby like Urban Outfitters, Free People, and Adidas.

For more, see my full list of my favorite Chicago thrift shops.

👉 Pro Tip: Bring a reusable bag with you while you shop!

Flat Iron Arts Building 

Take in local art inside this historic Wicker Park building.

📍 Google Maps | Phone: +1 847 809 2606 | Hours: 7 am – 10 pm daily 

Flat Iron Arts Building is a historic landmark located in the heart of Wicker Park at the corner of W North Ave and N Milwaukee Ave.

What was once an office building built in the early 20th century is now a thriving community of local artists. Today, studio spaces fill the space, and the halls are made up of art galleries, which the public can wander through for free.

Community events like “First Friday” are also held here, where studio doors are opened for the community to explore individual art galleries. The work features contemporary art, visual art, art installations, and sometimes, performance events are held. 

If you visit Wicker Park, it would be hard to miss this iconic destination. If you’re at all interested in art, stop by to take a peek at some of the incredible work by local artists. 

The Den Theatre

Get tickets to comedy shows, performances, and other events at this cozy, local theater. 

📍 Google Maps | Phone: (773) 697-3830 | Website | Hours: Showtimes vary | Tickets: $20-$50 

The Den Theatre is a performing arts theater located on Milwaukee Ave in Wicker Park. Generally, shows are for more mature audiences. They range from stand-up comedy to musical acts, discussions, and events like trivia. The Den Theatre brings in a mix of local performers and touring acts. 

The whole vibe of the Den Theatre is cozy and homey. It’s perfect for a fun evening activity or date night. The theater also has a bar and lounge. You can grab a drink and hang out before or after a show, or just visit for the good vibes.

Big Star

Enjoy tasty tacos and delicious margs in the center of Wicker Park.

📍 Google Maps | Phone: (773) 235-4039 | Big Star Website | Hours: 11 am – 10 pm Mon – Thu, 11 am – 11 pm Fri, 10:30 am – 11 pm Sat, 10:30 am – 10 pm Sun 

Stop by Big Star for a buzzing atmosphere and tasty tacos inspired by Mexican street food. Located in the center of Wicker Park, this Chicago restaurant is a local favorite.

Big Star is casual and laid back, and has a great outdoor patio. In the summer especially, it’s the perfect place to come for a fun meal with friends and split a margarita pitcher. 

If you’re in a bit of a time crunch, pick up tacos at the taco window instead of going into the restaurant. 

👉 Pro Tip: If you’re wondering how to get from Point A to Point B, then read these guides on how to get around in Chicago and driving in Chicago. Also, check out Discover Cars to compare rates on car rentals.

Dorian’s

Step inside a hidden cocktail bar and intimate live music venue.

📍 Google Maps | Phone: (773) 687-9824 | Dorian’s Website | Hours: 6 pm – 1 am Tue – Thu & Sun, 6 pm – 2 am Fri & Sat | Entrance: $10 adults 21+ 

If you walked by Dorian’s you’d never think there was a speakeasy-like music venue hidden behind a couple of doors. But a step “through the record shop” reveals a unique experience for locals and visitors alike. 

The music venue is an intimate performance space where you can enjoy live music by local artists, up close. Dorian’s also has a tasty selection of house cocktails and drinks for sharing.

The first time I visited, I was blown away by the local talent. Dorian’s is a real treat for music lovers and those who want to enjoy a little something different.

The 606 Bloomingdale Trail

Get moving on Chicago’s elevated greenway.

📍 Google Maps | Phone: (312) 742-4622 | 606 Website | Hours: 6 am – 11 pm daily 

One thing that sets Chicago apart from other big cities is its green space. The “606,” also known as the Bloomingdale Trail, is a 2.7-mile elevated greenway that’s perfect for running, biking, and walking.

Wicker Park is lucky to have two main access points within the neighborhood. These access points can be reached from Damen Ave and N Milwaukee Ave.

The trail itself is surrounded by residential streets and tons of trees, flowers, and landscaping. If you’re looking to get active, this is a great escape. 

🚶 How to Get There: Take the Blue Line and get off at either Damen or Western (depending on which access point you want). The two Wicker Park & Bucktown access points are listed as “Park No. 567” on N Milwaukee Ave and “Churchill Field Park” on N Damen Ave.

Wicker Park Farmers Market

Enjoy a slow Sunday morning and picnic in (actual) Wicker Park.

📍 Google Maps | Phone: (773) 384-2672 | Wicker Park Farmers Market Website | Hours: 8 am – 2 pm Sun (summer season) 

Depending on what time of year you visit Chicago, you can spend your Sunday mornings at the Wicker Park Farmers Market (during the summer season).

This farmers market takes place in actual Wicker Park, which is just next door to Big Star and a quick walk from the Damen stop. 

Here, tons of local farm vendors set up shop and sell a variety of fresh, seasonal produce, as well as artisan goods like bread, cheese, and baked goods. Many vendors even serve made-to-order food like crepes and waffles, so you can enjoy a tasty breakfast as well as some green space in the park.

📚 Related Reading: 33 Best Things to Do in Chicago (By a Local)

Reckless Records

Get your music fix at Chicago’s go-to record store.

📍 Google Maps | Phone: (773) 235-3727 | Reckless Website | Hours: 10 am – 7 pm daily 

This Wicker Park record store is sure to have music lovers head over heels. Located on N Milwaukee Ave, Reckless Records boasts an impressive selection of used vinyl, as well as CDs, DVDs, cassettes, and video games. 

If you’re looking for a record, regardless of genre, they’re likely to have it. And don’t worry, they sell new records, too! Reckless Records also has locations in the Loop and in Lakeview.

Jackson Junge Gallery

Visit this unique, local gallery that features the work of Laura Lee Junge and other Chicago artists. 

📍 Google Maps | Phone: (773) 227-7900 | Website | Hours: 11 am – 8 pm daily, closes 7 pm on Sundays | Entrance: Free

Jackson Junge Gallery is easy to miss when visiting Wicker Park, but it shouldn’t be! This unique, local art gallery is located right on Milwaukee Ave.

It showcases the work of Chicago artist Laura Lee Junge (who is co-owner of the gallery), as well as work by other Chicago artists. The artwork on display is often colorful and thought-provoking. There are usually tables featuring locally-made gifts and objects for purchase as well. 

Overall, Jackson Junge Gallery is just a cool spot to stop in and wander around while you’re exploring Wicker Park.

Emporium Arcade Bar

Have fun with friends at this unique arcade bar and entertainment venue.

📍 Google Maps | Phone: (312) 450-0246 | Emporium Website | Hours: 5 pm – 2 am Mon – Thu, 3 pm – 2 am Fri, 12 pm – 3 am Sat, 12 pm – 2 am Sun | Event Tickets: $20+ 

Emporium Arcade Bar is a fun and lively spot perfect for friends and larger groups. Part bar, part live entertainment venue, and part arcade, this Wicker Park Emporium always has something to do. Think air hockey, pinball machines, and tons of video game machines.

If arcades aren’t your thing, check out their lineup of events ranging from themed DJ nights to live music and tournaments. The dive bar atmosphere is fun, colorful, and is sure to be a throwback with its selection of childhood arcade games.

Quimby’s Bookstore

This bookstore focuses on comic books, magazines, and independently made and published works. 

📍 Google Maps | Phone: (773) 342-0910 | Website | Hours: 12 pm – 6 pm Thu – Mon, Closed Tue & Wed

Quimby’s Bookstore is an indie bookstore on W North Ave. It’s perfect for those interested in comic books, magazines, and unconventional titles. Quimby’s is also known for having independently published works including zines, which you won’t find in most other bookstores. 

Quimby’s has a quirky but cozy vibe. You can shop for books as well as weird, little gifts and objects. Quimby’s isn’t the bookstore for everyone but I’d recommend it to those who like indie and off-beat books.

Wicker Park Fest

Celebrate music, culture, and food at one of Chicago’s best street festivals.

📍 Google Maps | Phone: (773) 384-2672 | Wicker Park Fest Website | Season: summer | Entrance: $10 donations 

Chicago in the summer is truly unmatched, and this is partly due to the incredible events and festivals that take place in each neighborhood around the city. For the Wicker Park community especially, the Wicker Park Fest is a true highlight. 

This Chicago street festival that takes place between N Milwaukee Avenue and N Paulina Street is a fun-filled weekend of music, local food, as well as arts, crafts, and local retail.

The Chicago Tribune even named Wicker Park Fest “Chicago’s Best Street Festival of the Summer.” If you’re a local or happen to be in town for this one, you won’t want to miss it.

The Robey Hotel

Enjoy brunch, drinks, and views at Wicker Park’s tallest building.

📍 Google Maps | Phone: (872) 315-3050 | The Robey Website | Hours vary for Cafe Robey, The Up Room, and Cabana Club 

Wicker Park is one of the best areas to stay in Chicago, but even if you’re not staying at The Robey hotel, this historic building still has a lot to offer.

On the first floor, Cafe Robey offers brunch and dinner with some classic American fare. Up on the 6th floor is Cabana Club, where non-guests can enjoy drinks and stunning views of Wicker Park and the Chicago skyline. 

For even higher views, head to The Up Room lounge on the 13th floor. Here, you can sip a drink while enjoying a cozy atmosphere and more beautiful views. From The Up Room’s terrace, you can look up to see The Robey’s spire up close.

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That’s a wrap! I hope my guide will help you make the most out of a fun-filled day in Wicker Park. For more ideas, check out our list of top things to do in Chicago!