This Week in Lincoln Park & Old Town: Art Fest Finale, Steppenwolf Opening

Your week-ahead guide to Lincoln Park and Old Town — 4 picks from street festivals to Steppenwolf.

By Raj Singh · Published June 14, 2026.

Old Town anchors the week in a good way: Sunday is the final day of the 51st Annual Wells Street Art Festival, which transforms North Wells into an outdoor gallery from 10AM to 9PM. Once the festival wraps, the neighborhood shifts into theater mode — Steppenwolf opens a new production mid-week, and a free Route 66 film screening lands at the Chicago History Museum on Wednesday.

SUNDAY 6/14 — 51st Annual Wells Street Art Festival @ Old Town (Old Town)

Today is Day 2 and the final day of the Wells Street Art Festival — the oldest and most prestigious street art fair in the neighborhood, running along 1200–1600 N. Wells from 10AM to 9PM. More than 200 juried artists show painting, sculpture, jewelry, and photography lining the historic block. It falls on Father's Day weekend, making it a natural family afternoon.

1400 N. Wells St., Old Town. 10:00AM–9:00PM. Free to browse. Old Jerusalem Restaurant (1411 N. Wells, steps from the main block) does a generous falafel plate and fresh-squeezed lemonade that hits right in the afternoon heat.

SUNDAY 6/14 — Chicago Comedy Hour @ de Maat Theatre at Second City (Old Town)

Second City's de Maat Theatre hosts this late-night variety showcase — sketch, improv, and stand-up from some of Chicago's best up-and-coming comics, curated in rotating lineups you won't see replicated. It's a good pairing for an art fest Sunday: browse Wells Street all afternoon, eat dinner, then catch the late show.

230 W. North Ave., Old Town. 9:00PM. $25. Bar opens early; the Second City crowd tends to hang late.

TUESDAY 6/16 — Catch As Catch Can @ Steppenwolf Downstairs Theater (Lincoln Park)

Steppenwolf's Downstairs Theater opens this new production Tuesday night. When a prodigal son returns to blue-collar New England, his homecoming sets off a spiraling crisis for two families — a compact drama about the weight of what we owe each other and to whom. The Downstairs is the more intimate of Steppenwolf's stages; sightlines are excellent from every seat.

1650 N. Halsted St., Lincoln Park. 7:30PM through the weekend. Tickets at steppenwolf.org. Dinner beforehand: Boka (1729 N. Halsted) is a Michelin-starred room around the corner — book a week out or try the bar walk-ins.

WEDNESDAY 6/17 — Summer Screenings: On the Road Again @ Chicago History Museum (Lincoln Park)

In honor of Route 66's 100th anniversary, the Summer Screenings series celebrates the great American road movie — the journey-as-destination genre, from classic Hollywood to indie. The Chicago History Museum's Lincoln Park location is one of the city's most underused gems. Check the CHM website for the specific film and outdoor vs. indoor screening details.

Chicago History Museum, 1601 N. Clark St., Lincoln Park. 6:30PM. Great pre-show: Café Ba-Ba-Reeba (2024 N. Halsted) does Spanish tapas — the patatas bravas and chorizo-stuffed peppers are the move before a movie.

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