A guide of what to do in Wicker Park, Chicago – this hipster neighborhood will seem familiar if you are a fan of High Fidelity since much of the 2000 John Cusack film was shot here.
Wicker Park is to Chicago what Brooklyn is to New York City. It’s that effortlessly cool neighborhood. And like Brooklyn, it feels like a neighborhood – a place where people actually live – instead of an area filled with office buildings.
Wicker Park has it all: great restaurants, lots of independent boutiques, bookshops, coffee houses, music venues, vintage shopping, and a lively nightlife. Charles and I love it so much that it’s the neighborhood we are moving to next.
Where is Wicker Park?
Wicker Park is located northwest of downtown Chicago. The southern border is Division Street, the western border is Western Avenue, the eastern border is Ashland Avenue, and the northern border is West Bloomingdale Avenue. This neighborhood is considerably smaller than Lincoln Park or Lakeview and is very walkable.
Getting to Wicker Park
The easiest way to get to Wicker Park is to take the Blue Line to the Damen or Division stop.
What to do in Wicker Park
Walk the Bloomingdale Trail (The 606)
This 2.7 mile elevated trail for bikers and runners goes along the north edge of Wicker Park and incorporates art installations and landscape design. Locals tend to call the trail “The 606” but if you want to get technical, the elevated walkway is the Bloomingdale Trail which is a part of the The 606. The 606 includes six street level parks (two aren’t complete yet) and the Bloomingdale Trail.
The park named Wicker Park is a small triangular park in the center of the Wicker Park neighborhood. This 4 acre park is tiny in comparison to Lincoln Park, Oz Park, or Grant Park. The park contains a fountain, a dog park, a baseball diamond, a football/soccer field, a water playground, and a walking path.
You can find a mix of vendors selling produce, prepared food products, spices, juice, and meat at this market. Plus, several restaurants participate in the market.
The Wicker Park Farmers Market takes place in Wicker Park from 8 am – 2 pm on Sundays in the Spring, Summer, and Fall. From December to April the market takes place at The Robey Hall (2022 W. North Ave) from 10 am to 3 pm on Saturdays.
A two floor live music venue that hosts a wide variety of bands and events. Not many venues have a reggae concert one night and emo night the next.
A theatre and performance space that hosts plays, concerts, DJs, and standup comedy.
Searching for street art is a fun thing to do as you explore the neighborhood. You will find large murals that completely cover the sides of buildings, and smaller works tucked away in alleyways.
Unlike the vast majority of comedy clubs, this stand-up and improv club is BYOB. Most shows are just $8 for advance online purchases and $12 at the door – this is a great place for a cheap night out!
Where to Eat in Wicker Park
A Tex-Mex diner with a tequila and mezcal focused bar menu, this is a diner with a counter service and exceptional food. Menu items included burnt ends hash, buttermilk fried chicken, and chile relleno. It’s one of the only places where you can find a papusa in Chicago.
One of the most beloved restaurants in Chicago, Big Star has a take out window and a restaurant with a big sunny patio. Big Star is known for serving up delicious guacamole with freshly made chips, strong pitchers of margaritas, and a variety of tacos. The panza and al pastor tacos have been on the menu since the start and are must try menu items. I’m also a sucker for the walking taco.
An old school red sauce Italian restaurant with a big menu of pastas and meat dishes. Charles loves the meatball salad and I love the alfredo. This place is popular, so make sure you make a reservation.
Piece is one of Chicago’s most beloved pizzerias, and likely the reason why Charles is so desperate to move to Wicker Park. The pizza here is New Haven style thin crust and available in small, medium, and large sizes. Piece is known for collaborating with other Chicago restaurants and chefs, you can get pizza topped with Hot Doug’s sausage or Honey Butter Fried Chicken. It’s also one of the only places where I’ve seen mashed potatoes as a pizza topping option.
Pub Royale is a British style pub that serves Indian food. I love everything about this place, it has a great British pub atmosphere that brings me back to London and the food and drinks are fantastic. I especially love the butter paneer, the eggplant curry, and the royale burger.
Kanela has a handful of locations throughout the city, and there are two in Wicker Park (one of Milwaukee and one on Division). They serve brunch everyday, and the menu has just the right mix of breakfast and lunch options. I usually get the goat cheese omelette or the grilled cheese.
Another brunch spot, Bongo Room focuses more on the breakfast side of brunch with a menu filled with egg dishes and sweet meals like pancakes and french toast. They are especially known for their pancakes that come in flavors like white chocolate and caramel pretzel, pumpkin spice, and caramelized apple.
A cafe that specializes in vegan food – but the menu is so good you might not even realize all the food is plant-based.
A sister restaurant to Happy Camper in Old Town and Homeslice in Lincoln Park, Paradise Park is more about the party than the pizza. The space has a large patio and rooftop where people drink the weekends away.
A street level restaurant attached to The Robey hotel, this cafe has a separate entrance so it doesn’t have that hotel restaurant vibe. Instead, it’s bright, sunny, and welcoming. They serve brunch, lunch, and dinner with their brunch menu focusing on classics like egg dishes, hash, pancakes, and sandwiches.
James Beard award winning Chef Mindy Segal’s restaurant serves much more than sweet treats – although you definitely need to save room for those. The restaurant serves brunch, lunch, and dinner and the menu has items like squid ink tagliatelle, risotto, a burger, and a 60 day dry aged pork chop. Brunch has a nice mix of sweet and savory – with over the top french toasts being one of the more popular meals. I also recommend trying the hot chocolate and some of the cookies.
There was a time when getting a reservation was nearly impossible since Schwa wasn’t using any online booking platforms. Now that they are using Tock, things are easier. Schwa pairs fine dining cuisine with a casual atmosphere and it’s one of the best meals I have ever tasted. They serve a multi course (10+ courses) prix fixe menu and it’s BYOB.
A fast casual taco joint with patio seating and a menu that blends Mexican with Midwest. Find guacamole, queso, chili cheese curds, pork carnitas tacos, and more on the menu.
A Roman pizza spot with a couple of Chicago locations, this pizza is on a thicker focaccia-like crust and displayed along the counter. You then tell the staff which pizza and how much you would like and they cut you a slice. You pay for the pizza based on the weight. My favorite pizza is topped with zucchini, lots of fresh ricotta, and lemon juice.
A donut shop that’s sells both old fashioned (cake-like) doughnuts and yeast doughnuts. I love the pistachio and the biscoff pocket.
A beautiful neighborhood Italian restaurant serving pastas and wood-fired food. Their pastas are hand made in house and are used to make dishes like bucatini cacio e pepe and cavatelli bolognese.
What started as a food truck has evolved into multiple restaurants that serve over the top grilled cheeses. One of the most insane: a grilled cheese filled with mac and cheese.
You can simply get a bagel or you can order a bagel sandwich or soup from the menu at this shop located beside Piece.
A casual spot serving up tacos, sharable places, and a variety of dips. I am a big fan of their avocado pine nut puree and their beef barbacoa tacos.
An Asian restaurant that is committed to serving fresh food made with meat that is free of antibiotics, hormones, and steroids. The menu has vegan, vegetarian, and gluten free options. MAK is in the regular rotation of restaurants that I get delivery from. I love their chicken bowl and their fried rice.
Another pizzeria with a big patio and a party atmosphere, Parlor has the most insane pizza bread that comes topped with mozzarella and scallion cream. They also have a very solid menu of pizzas that include classic and more creative options all with funny names like the Cheesus, Mary & Joseph.
An East Asian restaurant serving up meals like Szechuan pepper shrimp, miso rubbed pork chops, everything chicken wings, and a mussel hot pot. Their burger is very popular and only available at the bar.
Coffeeshops in Wicker Park
A coffee shop beside the Bloomingdale Trail that serves a few sandwiches, beer, and cocktails in addition to coffee.
A spacious coffeeshop on Milwaukee with an ’80s theme and a DeLorean.
The front half of this space is a coffeeshop/bar and the back half is a bookshop. Volumes is on this list twice since I love stopping in for a drink and shopping here.
Is there anything more Wicker Park than a coffee shop/record store?
Where to Drink in Wicker Park
A James Beard Award winning cocktail bar located across the street from Big Star. There is no sign, just a light above a doorway to mark the entrance. The cocktail menu has classics and the mixologists’ own creations. All are complex and paired with ice that melts at just the right rate for that specific drink.
This is one of my all-time favorite cocktail bars. It’s got everything, top notch drinks, a friendly bar staff, and a romantic ambiance. The most unique thing about this bar is the layout of the bar – guests can sit on either side of the bar so that you can sip your drink while sitting across from your date. It makes the candlelit space even more romantic.
A pub that serves a menu of sausages and snacks along with a wide choice of beers, spirits, and cocktails.
The Rainbo Club
This Chicago institution was featured in High Fidelity, and has been around since the 1930s when it was a burlesque bar. The dive bar serves cheap draft beer and is a hangout for musicians and artists. In the ’90s Liz Phair hung out here and shot her Exile in Guyville cover in the Photo Booth. The Rainbo Club is also known to be a stop on the Tamale Man’s route.
Innjoy is my favorite spot for a night out with friends. On Saturdays they have an ’80s vs ’90s dance party where they play retro hits along with the music videos.
Where to Shop in Wicker Park
Wicker Park has a mix of locally owned independent boutiques and recognizable national brands. Most of the larger brands have locations the on small stretch of Damen Avenue between North Avenue and Willow Street. This is where you can find Lululemon, Toms, The North Face, Marine Layer, Cynthia Rowley, Fjallraven, Club Monaco, and more. This small stretch of the neighborhood differs from the rest of the neighborhood where most shops are locally owned. I have decided to focus on shops that are unique to Wicker Park here.
This shop is part coffee house, part bar, and part book store. It’s also a venue for literary events like a happy hour book club, author events, story time for children, and open mic spoken word performances.
This book store has a large collection of independent zines, comic booklets, and unusual publications. I love this shop because you can find things that you just won’t see anywhere else. The shop often hosts events too.
A sprawling bookshop with an inventory of over 70,000 used books. They also host events like an experimental music series, book readings, and poet talks.
Men’s clothing, sneakers, and skateboards are the main items sold at this large skate shop.
Shop locally produced Chicago-themed products including tee shirts, coasters, posters and more here.
I love this store where you can select a tee shirt, long sleeved shirt, or sweatshirt in a wide range of colors and then custom design it. It’s where I got the Andiamo shirt that I wore in Italy.
The cooler company with a cult following has a new flagship store in the heart of Wicker Park. It even has a bar so you can buy a yeti mug and fill it with a beer or coffee. On weekends they show sporting events on a massive tv.
This shop is geared towards men and women who like to explore. Find a mix of apparel, backpacks, outerwear, travel books, and other supplies for the adventurous here. I love the selection of clothing – I got a great sweater for myself and a tee for Charles that says “Whiskey will do”.
This Chicago-based company has several locations. They focus on women’s clothing specifically geared towards young women. It’s the perfect place to pick up an outfit for a night of clubbing or a music festival.
A women’s clothing and jewelry shop with three locations in Chicago, Enaz has trendy yet sophisticated clothing for women in their 20s and 30s.
A girly store with cards, party supplies, home decor items, and gifts. This is the perfect place to get supplies if you are hosting a party.
Belmont Army is a boutique with a mix of casual men’s and women’s clothing on the first level and in the basement you will find an army surplus store.
A store selling beauty products made by brands under the Deciem umbrella. The store has a cult following and affordable price points.
A store specializing in streetwear and footwear like crisp white Air Force 1s, graphic tees, and hoodies.
A shop selling “tools for nomads”. They have eyewear, notebooks, travel essentials, slippers, backpacks, and more.
Shop men’s and women’s apparel at this Milwaukee Avenue store. They have lots of clever graphic tees for men.
The primary item sold here is leather jackets but they also have some men’s apparel.
A large boutique selling clothing for both men and women. They have a big selection of denim and offer in-house hemming and denim repairs. They also sell footwear and jackets.
A shoe store that showcases the unique and colorful designs of John Fluevog. This location has been open since 1999 and his designs have been worn by musicians including Alice Cooper, George Clinton, and Jack White. He created the shoes for Anna Sui’s 2019 and 2020 runway shows.
This brand was founded by MIT grads, Ministry of Supply sells high performance clothing for men and women. They sell clothing that is fitting for the office as well as casual wear.
Vintage and Secondhand Shopping in Wicker Park
The Wicker Park record store in High Fidelity wasn’t real, but it reminds me of Reckless Records that sells secondhand vinyl.
US #1 Vintage
This vintage shop has a Western theme. You can find cowboy boots, Western shirts, and suede jackets for both men and women here.
The ’80s and ’90s vibes are strong that this store that sells neon clothing, stonewashed denim, and nostalgia inducing items like The Babysitters Club movie on VHS and cassette tapes.
Chicagoans in need of an ugly sweater flock here in December. Ragstock has a few locations and sells a mix of new and vintage clothing for both men and women.
A neatly organized resale boutique that specializes in tees and sneakers. It’s a store for casual second hand clothing.
Annual Events in Wicker Park
One of the largest street festivals in Chicago, Do Division is a three-day music festival, food festival, and sidewalk sale that takes place at the end of May. Two music stages are curated by The Empty Bottle and Subterranean. There is also a Family Fun Fest that takes place as part of this street festival and it includes a petting zoo, mega slide, and a stage with kid’s music. Do Division has a $10 entrance fee.
Wicker Park Fest
This Friday-Sunday street festival that takes place at the end of July has a music lineup curated by Suberranean and dozens of retail vendors in addition to food from several local restaurants. With four stages of music and over 50 bands performing, this is a music-centric event. There is even a special lineup of music for kids at Wicker Park Fest Kids Fest. There is a $10 donation/entrance fee.
This pop up music festival involves bands performing in storefronts in Wicker Park and Bucktown. It takes place in February and the goal is to bring music and shopping together while celebrating the neighborhood’s creative roots.
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