Neighborhood Festivals

From late May to September, it seems like there's always a street festival going on somewhere in Chicago. Neighborhoods close a few blocks of a main street, put up two or three stages, and throw a weekend party. Some fests celebrate the neighborhood itself, some are built around food or art, and some celebrate a community's heritage, from Swedish Andersonville to Mexican Pilsen. For a visitor, they're one of the easiest ways to see a part of the city most tourists skip, with a beer in hand.

>> read about free events in Grant Park

How they work

While the theme and location of each festival differ, they all follow roughly the same pattern. Most run Friday evening through Sunday. There's a gate at each end, and volunteers ask for a suggested donation, usually $10 to $20. At each one you'll find drink tents and food from neighborhood restaurants, live music from local bands, the occasional bigger name and at least one cover band, vendors selling everything from vintage clothes to handmade jewelry, and a whole bunch of locals relaxing in the sun.

That donation matters more than it looks. Most street fests aren't city events. They're the main fundraisers for local chambers of commerce and neighborhood groups, which pay for the stages, fencing, permits, security and portable toilets themselves. More than 30 of those nonprofits have banded together as the Save Our Street Fests Coalition, warning that rising costs and falling gate donations put some festivals at risk of closing. The organizers of Wicker Park Fest, which helped start the coalition, say so plainly. So pay at the gate if you can. Nobody's going to stop you if you can't.

Some fests have more of a "single and mingle" vibe, especially in Lakeview and Wicker Park after dark, while others are perfectly appropriate for kids, with family areas and bouncy houses. It's not unusual to see several generations at one fest. A set of young parents will rock out to the band while the grandparents drink some beers and watch the baby play on a picnic blanket at their feet.

The ones worth planning around

Here are some of the long-running fests to mark on your summer calendar, in roughly the order they happen. Dates change every year, so check each organizer's site.

Late May

The season starts over Memorial Day weekend with the Belmont-Sheffield Music Festival in Lakeview, run by the Lakeview East Chamber of Commerce. Do Division Street Fest in West Town, with two music stages, usually follows in late May or early June, and Lincoln Square holds its German Maifest around the same time.

June

Andersonville Midsommarfest has been running for more than 50 years. It fills Clark Street in Andersonville and celebrates both the neighborhood's Swedish roots and its LGBTQ+ community. The Andersonville Chamber of Commerce asks a $10 suggested donation. Take the Red Line to Berwyn and walk west, or catch the 22 Clark bus.

The Old Town Art Fair brings more than 200 artists to the Old Town Triangle, and the Wells Street Art Festival runs a few blocks away on the same weekend, so you can do both in an afternoon. Down in Hyde Park, the 57th Street Art Fair is the city's oldest juried art fair.

Taste of Randolph is the West Loop's food fest, run by the West Loop Community Organization on Randolph Street's restaurant row. It's one of the few with free entry at the gate. Chicago Pride Fest in Northalsted comes a week or so before the Pride Parade, and it asks a bigger donation than most. See our gay Chicago page.

July

Square Roots is Lincoln Square's fest, put on with the Old Town School of Folk Music, so the lineup is better than most. It runs on Lincoln Avenue between Montrose and Wilson, a short walk from the Western stop on the Brown Line, and gate donations help pay for the school's music scholarships.

Wicker Park Fest started in 2004 and books more than 50 indie bands, many of them local and on the way up. It runs on Milwaukee Avenue from Division Street to the six-way intersection at North and Damen, right by the Damen stop on the Blue Line, with a $10 donation encouraged. The Chicago Tribune once called it the best street festival of the summer, and if you only go to one, make it this one. It's a good excuse to explore Bucktown next door.

Other July regulars include the Southport Art Fest, Burger Fest in Roscoe Village, Taste of Lincoln Avenue, which has been going for more than four decades, Fiesta del Sol in Pilsen, and the Chinatown Summer Fair.

August

Northalsted Market Days is the big one, a weekend of LGBTQ+ celebration with multiple stages on Halsted Street. Taste of Greektown fills Halsted a bit further south near the end of the month, and Rogers Park has the Glenwood Avenue Arts Fest.

September

Retro on Roscoe has run for more than 30 years and is one of the last fests of the season. It takes over six blocks of Roscoe Street between Damen and Leavitt with three stages of music heavy on oldies and throwbacks, plus a classic car show with more than 50 cars. It's the main fundraiser for Roscoe Village Neighbors, and the suggested donation is $15. Lincoln Square's German American Oktoberfest and Old Town Oktoberfest also fall in September.

Where to find this year's calendar

The old Explore Chicago site we used to link is long gone. The city's tourism office is now Choose Chicago, and its festival and event guide lists street fests month by month with dates. The Save Our Street Fests site lists its member fests with dates and suggested donations. For the free city-run festivals, like Blues Fest and the Jazz Festival, see our holidays and events in Chicago page and Chicago in summer.

One tip. Most fests are in neighborhoods with little parking and lots of closed streets, so take the L or a bus. Our page on neighborhoods to visit by public transportation will help.

Photo by lobstar28