Every Chicagoan knows the telltale signs: the smell of kettle corn wafting through the air, oversized booths selling oversized lemonade, and a local indie band covering Mr. Brightside. Yes, that's right, streetfest season has returned to the city, and this summer there are more than ever to enjoy.
With so many unique variations offering specialty food, great music, refreshing drinks, and family-friendly activities, there's no better way to spend a warm weekend in Chicago than at one of the many streetfests spread out across downtown. So to help those on their sojourn into streetfests, here are some of Chicago Star’s favorite events happening through the summer season.
Do Division Street Fest
Traditionally, one of the first major street festivals to kick off the season, Do Division is a classic Chicago summer festival that offers a little something for everyone. Two live music stages are complemented by delicious finger foods and refreshing beverages from vendors across the city. The event also features a Family Fun section that includes bounce castles, games, and other entertainment perfect for those with little ones.
When: Friday, May 29 - Sunday, May 31
Where: Division Street between Damen and Leavitt
Old Town Art Fair
Weaving through the streets of the historic district, the Old Town Art Fair is a can’t-miss occasion for Windy City art lovers. Over 200 nationally acclaimed artists will descend upon the event, displaying world-class sculptures, tapestries, paintings, and more. The fest also features live music from some of Chicago’s best local bands, great food, and even a garden walk through some of the neighborhood's iconic homesteads.
When: Saturday, June 13 - Sunday, June 14
Where: Old Town Historic District
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Chicago Blues Fest
For those looking to get their groove on, look no further than the Chicago Blues Fest. Started in 1984, the event is marking its 41st birthday this year, celebrating the city's vibrant blues scene and storied history with the genre. The fest markets itself as the largest free blues festival in the world and features some of the most revered musicians in the industry. This year, festivities will kick off with a one-day panel session and concert experience on Thursday, June 4, at the Ramova Theatre in Bridgeport before returning to the event's primary location at Millennium Park for the remainder of the weekend.
When: Thursday, June 4 - Sunday, June 7
Where: Millennium Park
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Taste of Chicago
A timeless staple on the summer calendar, Taste of Chicago returns this year for its 46th annual fest in Grant Park. This year, the culinary showcase will bring together 84 food vendors and 20 food trucks representing some of the city's best and most unique bites all in one place. The event will also feature a live music stage with headliners, including R&B icon BabyFace and legendary Chicago rapper Common. Taste of Chicago is free to enter, but food and drinks are purchased on a ticketed basis.
When: Wednesday, July 8 - Sunday, July 12
Where: Grant Park
Wicker Park Fest
With roots stemming back to 2003, Wicker Park Fest has slowly grown over the last two decades into one of the city's most popular summer street events. The festival advertises itself as the definitive culmination of cutting-edge music, celebrated local restaurants, and unbeatable culture in Chicago, with the activity taking place along Milwaukee from North Avenue to Ashland Ave. Primarily known as a celebration of the neighborhood’s indie music heritage, this year the fest will host 50+ local and nationally recognized bands from a lineup curated by Wicker Park's popular nightclub, Subterranean.
When: Friday, July 24 - Sunday, July 26
Where: Milwaukee Avenue between North and Ashland
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