Young professional transplants to Chicago tend to gravitate toward apartments and condos as close to Lake Michigan as possible. As a result, some of the trendiest neighborhoods tend to be within a mile of the shoreline on the city’s North Side.
The Bucktown and Wicker Park neighborhoods buck that trend — they’re several miles away from the lake and just west of Interstate 90/94. The area invites 20-somethings who don’t need immediate access to lakefront running paths but still desire a neighborhood where they can enjoy age-appropriate activities and nightlife. The two border each other, but they blend geographically and culturally.
As with many neighborhoods in Chicago, Wicker Park and Bucktown were both European immigrant enclaves that have seen considerable changes in ethnic composition over the years. Through the 1990s, the neighborhoods had a large Puerto Rican community; gentrification over the past two decades led to a rise in property value and the Puerto Rican community moving west into Humboldt Park and elsewhere.
Unlike Lakeview and Lincoln Park, Bucktown and Wicker Park have something of an edge that provides a unique charm — they’re hotbeds for young artists and progressives, and it’s not uncommon to see left-leaning political statements peppering the streets and facades.
The heart of the area lays in the six-cornered intersection of North, Damen and Milwaukee avenues, where while standing in the middle of the street you can look any direction and find a wealth of restaurants, clubs, bars and boutique shops.
There’s a lot to do here, enough to warrant repeat visits. And with access right off Kennedy Expressway exits and the CTA Blue Line stop, visits aren’t hard to make.
It’s an ideal area to make a beeline for after rolling out of bed on a weekend morning with easy parking and lots of meal options in a small radius.
Feast Restaurant (1616 N. Damen Ave.) is one of the best places to have brunch in the spring and summer. On top of having stellar food — including chilaquiles, the garbage omelette and really tasty eggs Benedict — the available restaurant capacity almost doubles with the opening of a large outdoor patio that puts you right outside of the busy, people-watching-friendly North-Damen-Milwaukee intersection while you eat.
Even at its busiest, you usually won’t experience more than a 25-minute wait at Feast, unlike The Bongo Room (1470 N. Milwaukee Ave.), which is so popular that you could wait an hour for a table. It’s worth it, though, with the restaurant’s artisanal approach to traditional breakfast fare (the banana hazelnut pancakes with ground pralines are better than most normal humans could ever make). It makes sense why you’ll see a line of people stretched outside when passing the restaurant at certain times.
Wicker Park might be the epicenter of indie music in Chicago. No venue better captures the city’s fledgling hip-hop scene than Subterranean (2011 W. North Ave.). Right off the North-Damen-Milwaukee intersection, the two-floor establishment prides itself on theme nights, including reggae on Thursdays, Motown sounds on Fridays and open-mic hip-hop on Tuesdays. Many underground music acts that play Chicago make their way through Subterranean at some point.
The Double Door (1572 N. Milwaukee Ave.) is a spacious live music venue with a distinguished roster of previous performers, including the Rolling Stones and Sonic Youth, who have occupied the same stage as up-and-coming local acts. Until recently, the venue was identified mainly by the “Double Door Liquors” neon sign that one might confuse for a corner store. The young, bohemian element that makes up the neighborhood can often be found at the Double Door.
When the sun comes out and the days get long, Chicago is the place to go for block-shuttering street festivals. The Wicker Park Fest closes down Milwaukee Avenue between North Avenue and Paulina Street and sets up three stages, including one for kids, and several vendors. The $5 suggested donation will get you and the 70,000 other expected attendees plenty of family-friendly entertainment on July 26 and 27.
A vendor relaxes at his booth at the Bucktown Arts Fest.
Photo courtesy of the Bucktown Arts Fest Board.
Taking up considerably more space, the Bucktown Arts Fest is in and surrounding the Senior Citizens Memorial Park (2300 N. Oakley Ave.). The volunteer-run festival occupies a large part of the interior neighborhood, with artists from all over the country setting up booths off of Western and Fullerton avenues to display and sell their work. With more than 200 artists peddling every type of art from canvas-based to sculptures along with a carnival-style group of eating booths and several bands, dancers, poets and performing artists — you’ll need every moment of its Aug. 23 and 24 run to see everything.
Wicker Park’s Green Music Fest is a byproduct of the aforementioned progressive nature of the neighborhood: An environmentally conscious event that only uses “green” vendors, artists and craftmakers. Taking up Damen Avenue between North and Schiller avenues on June 21 and 22, the festival gives you everything its competitors offer (food, live bands, etc.) but with careful consideration for the planet, including compostable beer and wine cups, eco-friendly food services and the prohibition of plastic bottles and Styrofoam. Bring the young ones to the Green Kids’ Area to help them learn how to create a sustainable planet for their generations to enjoy.
Big Star (1531 N. Damen Ave.) is one of the most lively taco joints in all of the Midwest. Show up on a gorgeous Saturday summer evening looking for a table and you might get quoted a wait time that runs longer than “The Wolf of Wall Street.”
Taco joint Big Star is a popular place.
Photo by Cassie Stadnicki.
Much of its floor space is outdoor seating just off of Damen, though there is also limited seating surrounding the bar inside. The food and drink is authentic: Try any of the nearly two dozen tequilas neat or mixed in the house margaritas. Get the pork shoulder-based taco al pastor or the tilapia taco de pescado — and don’t be surprised when you ask the waiter for seconds.
Wicker Park has two main rib joints — Lillie’s Q (1856 W. North Ave.) and Smoke Daddy (1804 W. Division St.). They both have their merits, but Smoke Daddy takes the cake as not only the best in the neighborhood but the best in the city. Relatively nondescript on a block with many flashy facades, Smoke Daddy offers some fantastic portions for the price and more than enough sides and munchies to go with your baby backs or St. Louis-style spareribs. The pulled meat nachos and sweet potato fries are highly recommended. The place isn’t huge, but it’s big enough to fit live entertainment every evening.
Cafe LaGuardia (2111 W. Armitage Ave.) is one of the best places to get Cuban cuisine in Chicago. Located on a bustling block in Bucktown, the restaurant offers food authentic to the island, which is similar in spirit but distinct from the many authentic Mexican restaurants nearby. The paella valenciana is a scrumptious mixture of meat and seafood over yellow rice, and the jumbo shrimp catalina is filling and delicious. Every meal should start off with beef empanadas and end with the flan dessert.
A close neighbor to LaGuardia in cuisine, Irazu (1865 N. Milwaukee Ave.) caught a significant amount of buzz in the late aughts as Chicago’s only still-standing Costa Rican restaurant, leading to an expansion that helps take the heat off the long waits. The cash-only joint is perhaps most popular for its casado — an authentic dish made with ribeye steak, tilapia or chicken — and its killer oatmeal shake, which is as delicious as it is unique.
Myopic Books (1564 N. Milwaukee Ave.) is a wonderful anachronism — a throwback to the days of yore when dusty old bookstores were ubiquitous and Amazon didn’t ruin our need to ever visit one again. The three-level store keeps more than 80,000 books and houses a decidedly unkempt atmosphere that distinguishes it from, say, a pristine Barnes & Noble store and adds to its charm. You can even sell some of your old books on certain days and times. The space also houses one of the city’s longest-running experimental music venues, adding to the numerous places in the area to listen to music.
The Gorilla Tango Theatre (1919 N. Milwaukee Ave.) offers something you’re unlikely to find anywhere else in the city — burlesque parody shows. Adults-only offerings such as “A Nude Hope: A Star Wars Burlesque” make for an evening with a twist.
A plate of ribs at Smoke Daddy, which celebrated its 20th anniversary in May.
Photo courtesy of Michael Dunlay.
Until recently, Glazed and Infused (1576 N. Milwaukee Ave.) had the Wicker Park market on gourmet doughnuts cornered.
But just a few months ago, Stan’s Donuts & Coffee (1560 N. Damen Ave.) moved across the block in a bid to challenge Glazed for supremacy. The Los Angeles transplant holds court with a delicious array of doughy confections that make the scores of chain stores cower in shame. Intelligentsia is Stan’s coffee bean of choice, with mochas, chai lattes and the usual Starbucks-esque staples.
Glazed and Infused has tighter hours, closing at 2 or 3 p.m. every day and opening from 9 p.m. to 2 a.m. for late nights, and its doughnuts are delectable. Its fruit fritter is baked with various assorted fruits, and the apple bacon long john, a glazed doughnut with a strip of peppered maple bacon on top, is one of a kind.
In the mood for some permanent skin decorations? Check out Revolution Tattoo (2221 N. Western Ave.). Whether it’s your first piece or you need some serious work done, owner Omar Gutierrez and his crew of dedicated ink slingers have you covered.
Robin Richman (2108 N. Damen Ave.) was one of the first of what is now a number of specialty boutiques in Bucktown. The obscure international designer labels attract clientele looking for duds that are highly unlikely to be found elsewhere.
Reckless Records (1532 N. Milwaukee Ave.), like Myopic Books, is among the last of a dying breed — a spot where you can actually go and flip through crates to get that next record for your collection as well as sell some of your old vinyl. The owner of Reckless has announced plans to move the store to more spacious property not far away from the current location, which will allow for better live performances and even more room for LPs, DVDs and CDs.
iCream (1537 N. Milwaukee Ave.) offers a unique ice cream experience — similar to Cold Stone Creamery, only cooler. You choose a flavor of ice cream, sorbet, yogurt or more, then determine if you want it organic or dairy-free soy, then choose from all the mix-ins and toppings you can dream of. Watch your creation get mixed in a process that involves liquid nitrogen steam clouds. The results are tasty and delightful for children and adults.