Wicker Park Guide

Wicker Park, from the Front Door

A guide to the neighborhood, as we'd give it to a friend staying with us.

The thing nobody tells you about Wicker Park is that you don't really need a plan. Milwaukee Avenue runs diagonally through it like a fuse, and if you step out our front door and walk in any direction for ten minutes, you will find something — a record store, a handmade-pasta window, a patio full of people who look like they're in a band. This is a short list of our favorites, arranged roughly in the order you might encounter them over a day.

Morning

Candor Coffee — 1745 W Division St. right in the building, and the shortest walk you will take all day. A small, design-quiet room with a huge picture window facing Division, pale wood benches, and a single-origin menu that doesn't oversell itself. They pour Metric. Order a cortado, take the window seat, watch Division wake up.

Wake N Bakery — 1659 W Division St. If your mornings run more playful than monastic, Wake N Bakery is a block and a half east. Coffee, lemonades, pastries — all available with or without a cannabis lift. Loud, colorful, a little TikTok-y in the best way. Good for rainy afternoons and board games.

Lunch, or the start of a long afternoon

Tortello — 1746 W Division St. Directly across the street from Candor, and the reason several of our guests stay an extra night. A pastificio run by a Venetian (Dario Monni) and his wife, with everything made in-house by hand. Michelin Bib Gourmand three years running. Order at the counter, sit on the patio, get the tortelli. Take a pound of pasta home on your way out.

Big Star — 1531 N Damen Ave. Paul Kahan's taqueria, housed in a converted 1940s gas station at the six corners of Milwaukee, Damen, and North. The patio is, plainly, one of Chicago's great outdoor rooms. Al pastor, a margarita, a bourbon you can't pronounce. First-come, first-served — go at 2 p.m. on a Tuesday and you'll feel like you're getting away with something.

The afternoon wander

Milwaukee Avenue between Division and North is, block for block, one of the best walking streets in the Midwest. The shops we'd point you to: Vintage House Chicago (1433 N Milwaukee — new flagship, DJ, analog photo booth), Store B Vintage (1472 N Milwaukee — since 2001; Valentino, Saint Laurent, Prada, all repaired before they hit the floor), Round Two (1501 N Milwaukee — vintage shoes and tees), Kokorokoko (1323 N Milwaukee — a 90s kid's dream), and Ragstock (1459 N Milwaukee — a neighborhood standby). Also: Myopic Books for used paperbacks, Dusty Groove and Reckless Records for vinyl, and the dozen or so independent boutiques that have colonized the blocks west of Damen.

Early evening

Lilac Tiger — 1742 W Division St. South Asian, tiny, electric. Walk-in only — put your name down and use the wait to drift into the bars below. Chef Zubair Mohajir (two-time James Beard nominee) has a tasting-menu restaurant, Coach House, tucked behind it for anyone who wants a longer evening in his orbit. Order the THC sandwich (tandoori hot chicken, not the other thing), the Korean-curry-and-paneer fries, and whatever cocktail the bartender is proud of that week.

Paradise Park — 1913 W North Ave. A trailer-park-themed pizzeria and bar with disco balls, neon, a year-round patio, and a rooftop called Sunshine Daydream. Exactly as ridiculous as it sounds and exactly as fun. Solid pizza, long beer list, happy hour 3–6 weekdays. A great first-round, last-round, or group-of-eight room.

Late

Gold Star Bar — 1755 W Division St. A few doors down, and the most important address on this list. Gold Star has been on Division Street since around 1933 — nobody is completely sure when it opened, which is sort of the point. Nelson Algren drank here. So did Art Shay. The bar is dim, the music is good, the beer is cold and cheap, and the neon outside still reads "Rooms Furnished Rooms" — a ghost sign from when the upstairs was, depending on the decade, a boarding house or something less polite. Walk in, order a shot and a beer, and you are in a room that has been doing this for ninety years. We can't think of a better place to end the night.

A few notes for staying light on your feet

The Blue Line at Damen takes you to O'Hare one way and the Loop the other — both in about twenty minutes. The 606 Trail runs two blocks north of us, 2.7 miles west. Most of the places on this list are within a fifteen-minute walk of our front door. Wicker Park is a walking neighborhood first and a driving neighborhood distant second — park the car (or skip the rental) and let the streets do the work.

Come back at the end of the day, let yourself into the garden, pour a glass of something, and do nothing for a while. That's the whole idea.