The Wicker Park in Chicago under a clear blue sky

15 Best Things to Do in Wicker Park (By a Local)

Located in the northwestern corner of Chicago, there are a ton of great things to do in Wicker Park. Also known as Bucktown, this area is artsy and eclectic with tons of great restaurants, coffee shops, music venues, and secondhand shops.

As a Chicago local, I can tell you firsthand that there are tons of incredible Chicago neighborhoods, each with their own personalities. Wicker Park is easily one of my favorite neighborhoods in Chicago. You can reach it by taking the Blue Line to Damen, where you’ll be dropped right into the bustling central hub, known as “Six Corners.”

In this article, I’ll be covering the 15 best things to do in Wicker Park – but you can also check out our guide to the best things to do in Chicago.

Disclosure: Travel Lemming is an independent reader-supported blog. You can support us by purchasing via the affiliate links on this page, which may earn us commissions. Thank you!

15 Top Things to Do in Wicker Park, Chicago

Subterranean 

Enjoy live music at this local and intimate music venue

People watching the Ax and the Hatchetmen performing in Subterranean
Ax and the Hatchetmen performing, along with a few other bands

📍 Google Maps | Phone: (773) 278-6600 | Subterranean Website | Hours: 6:30 pm – 2 am daily (exact hours vary depending on show times) | Tickets: $10 – $20 

If you’re looking for a cool, local, and intimate music venue, this one 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. 

Proof of vaccination is still required for entry, so be sure to bring a physical or digital copy of your vaccine card. 

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

Chop Shop

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

View of Mindchatter performing in Chop Shop
Mindchatter, who recently performed at Coachella, performing at the Chop Shop

📍 Google Maps | Phone: (773) 537-4440 | Chop Shop Website | Hours: 5 pm – 9 pm Monday, Tuesday, 11 am – 9 pm Wednesday, Thursday, 11 am – 10 pm Friday, Saturday, 11 am – 5 pm Sunday | Tickets: $20+ 

The Chop Shop is an eatery, bar, and music venue located on W North Avenue in the heart of Wicker Park. Although people come here for delicious deli sandwiches and other American fare, 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.

👉 Pro Tip: Proof of vaccination is still required for entry, so be sure to bring a physical or digital copy of your vaccine card.

Violet Hour

Sip some of Chicago’s tastiest cocktails inside this intimate, speakeasy bar

A colorful mural in Violet Hour
The exterior wall is always covered by rotating murals

📍 Google Maps | Phone: (773) 252-1500 | Violet Hour Website | Hours: 5 pm – 1 am Wednesday – Sunday 

If you didn’t know about the Violet Hour, you’d probably walk right past its unsuspecting mural wall and not even realize there was a speakeasy behind it. But that’s part of the charm. 

For locals and visitors alike, Violet Hour is a Wicker Park institution that serves up some of the city’s best creative and classic cocktails. The cocktail menu rotates seasonally too, so there’s always something new to try. A visit to Violet Hour is perfect for date night, or to enjoy tasty drinks with friends.

Myopic Books

Browse floor-to-ceiling shelves of used books

View from an isle of bookshelf in Myopic Books
You’re sure to find some gems amongst their massive used book collection

📍 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.

Flat Iron Arts Building 

Take in local art inside this historic Wicker Park building

Colorful arts displayed inside Flat Iron Arts Building
Some hallway art displayed for the public

📍 Google Maps | Phone: (312) 566-9800 | Flat Iron Arts Website | 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. 

Big Star

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

View from the Big Star in Chicago
Sit on the patio for good food, great energy, and a real taste of Wicker Park

📍 Google Maps | Phone: (773) 235-4039 | Big Star Website | Hours: 11:30 am – 10 pm Monday – Thursday, 11:30 am – 11 pm Friday, 11 am – 11 pm Saturday, 11am – 10 pm Sunday 

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. The restaurant 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.

The 606 Bloomingdale Trail

Get moving on Chicago’s elevated greenway

The The 606 Bloomingdale Trail under the clear blue sky
The 606 connects a few different Chicago neighborhoods

📍 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.

Walgreens

Step inside the prettiest ever Walgreens

The Walgreens Pharmacy from the inside
Decorative, gilded ceilings

📍 Google Maps | Phone: (773) 342-9161 | Walgreens Website | Hours: 6 am – 12 am daily

You’re probably thinking, Walgreens? How on earth did this make the list? Hear me out. This Walgreens, which is located at the corner of N Milwaukee Avenue and N Damen Avenue in the center of Wicker Park, used to be a bank in the early 1900s. 

The outside of the building features some early 20th-century architecture, but the inside of the 3-story building is what’s especially cool. When you step inside, you’ll be greeted with tall, gold, and gilded ceilings—a sight worth snapping a few pictures of. Downstairs, they even have a “vitamin vault” with the original bank vault door and a wall of safety deposit boxes.

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

Wicker Park Farmers Market

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

View of people relaxing near the Wicker Park Fountain
Sit on a bench by the Wicker Park fountain to enjoy your farmers market goodies

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

Reckless Records

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

Vinyl displayed inside the Reckless Records
Spend at least an hour looking through their large selection of vinyl

📍 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 Lakeview.

Thrifting on N Milwaukee Avenue

Spend hours browsing vintage clothing and secondhand goods

Shirts and caps displayed inside the Round Two Store
Round Two has a cool, curated selection of vintage tees and jackets

📍 Google Maps | Phone: (773) 772-4296 | store B vintage Website | 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.

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

Emporium Arcade Bar

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

Different kinds of arcade games inside Emporium Arcade Bar
Tons of classic arcade games to choose from

📍 Google Maps | Phone: (773) 697-7922 | Emporium Website | Hours: 5 pm – 2 am Monday – Thursday, 3 pm – 2 am Friday, 12 pm – 3 am Saturday, 12 pm – 2 am Sunday | 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.

Dorian’s

Step inside a hidden cocktail bar and intimate live music venue 

View of Ivan Singh performing inside Dorian's
Ivan Singh performing—an up-and-coming blues guitarist

📍 Google Maps | Phone: (773) 687-9824 | Dorian’s Website | Hours: 6 pm – 1 am Wednesday, Thursday, Sunday, 6 pm – 2 am Friday, Saturday, Closed Monday & Tuesday | 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 an entirely unique experience for locals and visitors alike. 

The inside 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.

Wicker Park Fest

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

Performers in Wicker Park Fest in Chicago
This is a music-first festival with a great lineup of artists!

📍 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

View of The Robey Hotel in Chicago
The Robey—an iconic Wicker Park landmark

📍 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 on the 15 best things to do in Wicker Park. I hope my guide will help you make the most out of a fun-filled day in Wicker Park. For more ideas, check out all our Chicago travel guides.

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