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What to do in Wicker Park Chicago

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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. I moved to Wicker Park in 2021 and I am so thrilled to share my favorite spots with you!

A guide of what to do in Wicker Park, Chicago - a list of all the best restaurants, shops, coffee houses, bars, and things to do!

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.

Wicker Park

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.

Wicker Park Farmers Market

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.

The Den Theatre

A theatre and performance space that hosts plays, concerts, DJs, and standup comedy.

Street Art

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.

The Comedy Clubhouse

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!

Big Mini Putt Club

A 9 hole indoor mini golf course with a bar – It’s great group activity.

Where to Eat in Wicker Park

Looking for pizza? Read Where to Get Pizza in Wicker Park

The Rundown Nov 2018 7

Dove’s Luncheonette

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.


Big Star

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.


Tortello is a restaurant and pasta shop with a very special place in my heart. The pastas are exceptional. The large outdoor patio is charming and often has live music. You can buy pasta and ingredients to take home, or you can eat there. We do both. You can find me there buying fresh housemade pasta and burrata that comes fresh from Italy. I adore the cacio e pepe and the burrata filled tortelli.

Club Lucky

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 Brewery & Pizza

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.

The Perch

The Perch is our regular spot. The food is great and the service is excellent. Plus, they have a kids menu that is free from 4-6! We go at least once a week. We love the Wrightwood Salad, the Burger, and the Prime Rib. Their brunch menu is our favorite in the neighborhood too.

The Smoke Daddy

One of the best places in the city for barbecue – we love the ribs and the burnt ends.

Falafel and Grill

This Mediterranean restaurant is fast, affordable, and seriously good. We often get takeout from here when we don’t want to cook. We’ve tried most of the menu at this point and I recommend everything.

Pub Royale and Queen Mary Tavern 6

Pub Royale

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 Breakfast Club

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.

Bongo Room

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.

Native Foods

A cafe that specializes in vegan food – but the menu is so good you might not even realize all the food is plant-based.

Paradise Park

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.

The Robey Cafe

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.

Little Victories

Little Victories is a gastropub with a large outdoor patio and a chill vibe. The menu is small, and I could put this under the Where to Drink category, but the food is so good that it’s a big selling point for this spot. The burgers are fantastic – and creative – one has Sun Chips on top which is shockingly good. Also try the fried chicken and the short rib chili tots.

Craft Pizza

An excellent BYOB pizzeria serving up Neapolitan-style pizzas. They have a great Tuesday special too! I love this spot.


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.

Antique Taco

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.

Stan’s Donuts

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.

Cheesie’s Pub & Grill

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.

Takito Kitchen

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.

MAK (Modern Asian Kitchen)

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.

Parlor Pizza

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.

Mott Street

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

Wicker Park has A LOT of coffee shops – a separate blog post is going to take on this topic soon.

La Colombe

I am not much of a coffee drinker, but I’ll walk past 7 coffee shops to get the draft latte from La Colombe.


A coffee shop beside the Bloomingdale Trail that serves a few sandwiches, beer, and cocktails in addition to coffee.

The Wormhole Coffee

A spacious coffeeshop on Milwaukee with an ’80s theme and a DeLorean.

Where to Drink in Wicker Park

The Violet Hour

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.

Pub Royale and Queen Mary Tavern 4

Queen Mary

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.

Bangers and Lace

A pub that serves a menu of sausages and snacks along with a wide choice of beers, spirits, and cocktails. As of October 2021, they are hosting a Tamale Guy pop-up!

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 on the small stretch of Damen Avenue between North Avenue and Willow Street. This is where you can find Lululemon, The North Face, Marine Layer, 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.


Penelope’s specializes in casual men’s, women’s, and kid’s clothing and accessories.

Prery Collective

A new shop specializing in women’s clothing and accessories. Their goal is let customers shop all their favorite local brands in one space.


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.

The Red Balloon

A store for children that sells a wide range of toys, books, clothing, and other essentials. It’s the perfect place to buy a gift for a child or expecting parents.


This shop has locally produced goods including clothing, prints, ceramics, and more. It is a good spot to find a unique gift.


Located right next to Neighborly, Gemini sells men’s and women’s clothing and some home goods.

Myopic Books

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.

Secret Agent Supply Co

Every purchase from this children’s shop supports 826CHI’s free writing programs for children! This shop on Milwaukee just north of Division is so much fun. They have fun hats and disguises, toys, and lots of books.

Building Blocks

A toy store with a big selection of toys and books for children of all ages.


A bookstore, gallery space, and coffeeshop that showcases authors of color. The new space has murals, tables for working or reading, and a large children’s corner.

Field & Florist

A florist and shop selling home items, jewelry, and gifts.


You can find jewelry and jewelry making supplies, and yes, lots and lots of beads at this store.

Raw Edge

Raw Edge just opened on Division and sells goods from local makers and artists including prints, cards, clothing, jewelry, cosmetics, and more.


Men’s clothing, sneakers, and skateboards are the main items sold at this large skate shop.

Transit Tees

Shop locally produced Chicago-themed products including tee shirts, coasters, posters and more here.

The T-Shirt Deli

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 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.

Bow & Arrow

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

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.

St. Alfred

A store specializing in streetwear and footwear like crisp white Air Force 1s, graphic tees, and hoodies.

Top Drawer

A shop selling “tools for nomads”. They have eyewear, notebooks, travel essentials, slippers, backpacks, and more.

Mildblend Supply Co.

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.

John Fluevog Shoes

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.

Markets in Wicker Park


Foxtrot is a market, wine shop, and cafe that offers 60 minute delivery. We are huge fans and often pick up dips, salads, and wine here. Their wine selection is amazing!

Olivia’s Market

When compared to Foxtrot or Goddess, Olivia’s is more of a grocery option. They have a deli counter, produce, and a larger selection of groceries. It is also one of the best places in the neighborhood to buy flowers. Grab some Zingerman’s pimento cheese while you are there.

Goddess & Grocer

A cafe, bakery, and shop with wonderful desserts, sandwiches, grab and go meals, wine, beer, and more. They also offer catering.

Vintage and Secondhand Shopping in Wicker Park

Reckless Records

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.

Kokorokoko Vintage

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.

Round Two

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

Do Division

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.

Renegade Craft Fair

An absolutely massive outdoor craft fair with over 250 top-notch vendors that takes over a large stretch of Division Street each September.

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What to do in Wicker Park
What to do in the Gold Coast
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What to do in Downtown Chicago/The Loop
What to do in Lakeview
What to do in Streeterville

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