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Carefully curated vintage boutiques. Concept stores. Dive bars. A coffee shop with a DeLorean car. Shelves of used books. Does any of this sound interesting? You’ll find all of this and more in Wicker Park. Trust me — I used to live in this neighborhood!
Easily one of Chicago’s most popular areas, Wicker Park is best known for its trendy yet indie and youthful atmosphere. There are plenty of cool things to do over here. Some of my favorite Wicker Park spots even made my list of 75 best things to do in Chicago!
In this article, I’ll be covering all the best things to do in Wicker Park, including restaurants, coffee shops, music venues, shopping, and more.
Oh, and you can reach Wicker Park by taking the Blue Line to the Damen stop, where you’ll be dropped right into the bustling central hub, known as “Six Corners.”
Myopic BooksBrowse floor-to-ceiling shelves of used 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 shop has three floors, tons of smaller nooks, and sections for smaller genres. Myopic also hosts live music and reading events. For book lovers, this is a must-visit if you’re in the neighborhood.
Thrifting on N Milwaukee AvenueSpend hours browsing vintage clothing and secondhand goods.
Round Two has a cool, curated selection of vintage tees and jackets
📍 Google Maps | Phone: (773) 772-4296 | Hours: Vary per store
Wicker Park is known for its local shops, and the vintage clothing and secondhand stores along Milwaukee Avenue won’t disappoint.
Within one block is a huge roundup of thrift stores like store B vintage, Vintage Underground, Round Two, Vintage House Chicago, 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. It’s especially popular with younger crowds. If you don’t have any luck thrifting, though, there are other popular brands like Urban Outfitters, Free People, and Adidas along this same strip.
For more, see my full list of my favorite Chicago thrift shops.
👉 Pro Tip: Bring a reusable bag with you while you shop to avoid the local bag fee!
SubterraneanEnjoy live music at this local and intimate music venue.
Ax and the Hatchetmen performing, along with a few other bands
📍 Google Maps | Phone: (773) 278-6600 | Subterranean Website | Hours: Showtimes vary | Tickets: $20+
If you’re looking for a cool, 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.
Chop ShopCatch up-and-coming artists at this local music venue.
Mindchatter, who recently performed at Coachella, performing at the Chop Shop
📍 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 located in the back of the 100-year-old former auto-shop building is the main draw.
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.
The Den TheatreGet tickets to comedy shows, performances, and other events at this cozy, local theater.
Inside the Den Theatre
📍 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. Think everything from local theatre groups to popular names like John Mulaney.
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 StarEnjoy tasty tacos and delicious margs in the center of Wicker Park.
Sit on the patio for good food, great energy, and a real taste of Wicker Park
📍 Google Maps | Phone: (877) 298-0617 | Big Star Website | Hours: 11:30 am – 10 pm Mon – Thu, 11/11:30 am – 11 pm Fri & Sat, 11 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 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.
Dorian’sStep inside a hidden cocktail bar and intimate live music venue.
Ivan Singh performing — an up-and-coming blues guitarist
📍 Google Maps | Phone: (773) 687-9824 | Dorian’s Website | Hours: 6 pm – 1 am Tue – Thu & Sun, 6 pm – 2 am Fri & Sat, Closed Mon | Entrance: $10 cover for 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 TrailGet moving on Chicago’s elevated greenway.
The 606 connects a few different Chicago neighborhoods
📍 Google Maps (Access Point) | Phone: (312) 742-4622 | 606 Website | Hours: 6 am – 11 pm daily | Entrance: Free
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. And once you’re done, grab a coffee at Ipsento.
🚶 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.
The WormholeGo where the locals go and grab your morning coffee at this offbeat, sci-fi-themed cafe.
You can see the DeLorean in the back!
📍 Google Maps | Phone: (773) 661-2468 | Website | Hours: 7 am – 7 pm Mon – Fri, 8 am – 7 pm Sat & Sun
There’s a decent amount of cafes around Wicker Park. But if you’re wondering where to go, head straight to The Wormhole for a good cup of coffee.
As its quirky name likely suggests, this cafe is unpretentious with its friendly service, oddball decor (I mean, there’s literally a DeLorean replica from Back to the Future in the back…), and lived-in vibe. It feels like the type of place locals frequent because it quite literally is.
They’ve got good coffee and all your espresso classics. One of their most popular lattes is the Honey Bear, which includes local honey.
Wicker Park Farmers MarketEnjoy a slow Sunday morning and picnic in (actual) Wicker Park.
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 Sun (summer)
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 RecordsGet your music fix at Chicago’s go-to record store.
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’ll likely have it. And don’t worry, they sell new records, too! Reckless Records also has locations in the Loop and in Lakeview.
Flat Iron Arts BuildingTake in local art inside this historic Wicker Park building.
Some hallway art displayed for the public
📍 Google Maps | Phone: (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.
Built in the early 20th century, this former office building is now a thriving community of local artists. Today, studio spaces and art galleries fill the halls, which the public can wander through for free.
Community events like “First Fridays” 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.
If you visit Wicker Park, it’s hard to miss this iconic building. If you’re at all interested in art, stop by to take a peek at some of the incredible work by local artists.
Jackson Junge GalleryVisit this unique, local gallery that features the work of Laura Lee Junge and other Chicago artists.
A gallery wall of work by local artists
📍 Google Maps | Phone: (773) 227-7900 | Website | Hours: 11 am – 8 pm Mon – Sat, 11 am – 7 pm Sun | 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.
So, stop in and wander around the gallery while you’re exploring Wicker Park.
Emporium Arcade BarHave fun with friends at this unique arcade bar and entertainment venue.
Tons of classic arcade games to choose from
📍 Google Maps | Phone: (312) 450-0246 | Emporium Website | Hours: 5 pm – 2 am Mon – Thu, 3 pm – 2 am Fri & Sun, 3 pm – 3 am Sat | 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 BookstoreThis bookstore focuses on comic books, magazines, and independently made and published works.
Inside Quimby’s Bookstore
📍 Google Maps | Phone: (773) 342-0910 | Website | Hours: 12 pm – 7 pm daily
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 FestCelebrate music, culture, and food at one of Chicago’s best street festivals.
A band performing at Wicker Park Fest
📍 Google Maps | Phone: (773) 384-2672 | Wicker Park Fest Website | Season: summer | Entrance: $10 suggested donation
Chicago in the summer is truly unmatched, and this is partly due to the incredible events and local festivals that take place in each neighborhood around the city. In Wicker Park, the Wicker Park Fest is a true highlight.
This street festival takes place between N Milwaukee Avenue and N Paulina Street. It’s 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 HotelEnjoy brunch, drinks, and views at Wicker Park’s tallest building.
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, 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 my complete list of Chicago neighborhoods.