All summer, and actually well before, from the first drib drabs of sunlight in early March when the Empty Bottle puts on its mid-winter MUSIC FROZEN DANCING 2016 (the event debuted in 2014, complete with stand-up heaters) to the last standing man at Riot Fest (Sept. 16–18, Douglas Park), Chicago neighborhoods routinely close down their blocks, put up tables and stages, and take to the street for the annual parade of festivals.
Like many brutal-winter-enduring cities, Chicago comes raging to life in summer, for we know it flies by almost as fast as you can say, “Pajar parka!”
Chicago has more than 400 festivals each year. It boasts the biggest free classical music series (Grant Park Music Festival, which starts tonight, June 15, and runs until Aug. 20), and the largest dance series in the country (Chicago SummerDance, June 24–Sept. 11).
So, this will not be an exhaustive list, by any means. But we dug into the best of the fests to highlight some that give you lots of spectacle for a wee bit of cash.
What do people do?
At first blush, the epic amount of chilling going on at these events is almost embarrassing. There are definite detractors (Said in the most histper-esque tone, “I went for a few years, then got over it.”) But the casual nature of festivals offers many opportunities to meet new people and shop for local art, clothing, jewelry, and hand-crafts.
Thematically, festivals revolve around one or more of three things—art, music, and food. As far as I can tell, music fests are open-air beer gardens where friends from all around Chicago run into each other and day-drink while listening to world-class music.
The ones that center around art and food are more family-friendly and typically get more bar-like in the evening as the kids get cranky and families depart.
Neighborhood Pride in Festivals
You can schedule your festival itinerary by size, location, theme, or just chronologically, trying to hit as many as you can until September (or ‘til you drop).
Chicago is a city of neighborhoods (technically we have 77 of these!), and since we’ve been talking a lot about them, we thought we’d mention some of our favorite fests by theme as well as the neighborhood. Whichever hood you happen to live in, it probably hosts a couple of fests.
My first fest when I moved here six years ago was Maifest in my then-hood of Lincoln Square. Maifest (June 2-5) celebrates the continuing German heritage of the neighborhood with copious amounts sausages, nonstop polka bands, arcade games, lederhosen, and of course, easy-drinker pilsner by the liter (and by the liter, and by the liter, etc.). Neighborhood fests like Maifest, Rib Fest, and Square Roots Fest often make for the best fests, attracting lots of different types, from morning ‘til night.
Many of these weekend fests are neighborhood-centered and grassroots, like Logan Square Arts Fest (June 24–25) and the Wrigleyville Summerfest (Aug 6–7), World Fest (Albany Park, August), Reggae Fest (Pilsen, August).
From weekend DIY’s on Milwaukee Ave. (Chicago loves shutting down Milwaukee to party on) to the Puerto Rican Festival & Parade, which essentially takes over the Humboldt Park neighborhood in late June, these grassroots fests dot the calendar between the big boys like Chicago Blues Fest (June, Grant Park), Chicago Air & Water Show (Aug 20–21, lakefront), Taste of Chicago (July 6–10, Grant Park), Lollapalooza (July 28–31, Grant Park), and Gay Pride (June 18–19, Boystown/Lakeview).
What’d I miss?
Our hard-working agents couldn’t help us too much, here. Weekends are tough as they are Saturdays prime showing days for home tours. They echoed a common end of summer theme, though—the festivals they’ve missed already!
“It’s not always easy to get there,” said Michael Gerhardt, an agent with RE/MAX.
“With Lollapalooza and other concerts, and the neighborhood street fairs, the Air & Water Show, and the marathon, it’s overwhelming,” he said.
It’s a joke in Chicago that you hear about the highlights of each weekend either as they are happening, or after the fact. There is a significant risk of FOMO (fear of missing out).
Chiditarod (a shopping cart race and food drive, but that description don’t begin to cover it) happened ages ago. Printer’s Row Lit Fest was last weekend, as was Rib Fest, and Do Division the week before. But don’t worry, there’s still Windy City Ribfest in Uptown, Taste of Latin America, West Fest, and Wicker Park Fest in July, Pilsen’s food truck social (ongoing), and many others that are free or under a suggested donation of $10.
If art is your thing, Gerhardt suggested Old Town—the Wells St. Art Festival (June, Old Town), Randolph Street market (ongoing, Fulton Market), and Halsted Market Days (Aug. 13–14, Boystown), which hosts bigger acts than one would suspect at a small fest, including Salt ‘N Pepa and En Vogue last year.
That reminds me of the Hideout Block Party, which took last year off but we hope returns this fall. This small fest is the cherry on top of the summer music season in Chicago. Scheduled in early September, it routinely features blockbuster acts (Neko Case, Death Cab for Cutie), is cheap and it supports everyone’s favorite dive.
But the piece de resistance of the free festivals is surely the summer series in classical, world, and pop music at Millennium Park. These concerts, held in open-air under the spectacular Pritzker umbrella, feature the best music and are offered multiple nights a week.
Here in Chi-town we take a festival (or two) every weekend, add in a steady mixture of concerts, trips, Fourth of July plans, BBQs, and weddings, and call it summer. At the end of it, we may be bone-tired and ready to sleep for a week, but luckily, winter arrives a week later.
More Festival Info
See some festivals listed chronologically on City of Chicago’s website or more extensive listings on the Red Eye and other local sites.