Six Summer Street Festivals to Explore Across Chicago

Courtesy of VitalKopy MediaA performer entertains the crowd during the concert series during a past weekend of Do Division Street Fest which runs down Division Street, starting at Damen Avenue ending at Leavitt Street.

As the school year comes to a close and summer in Chicago blooms, those staying in the Windy City can check out a variety of street festivals from the Loop to the North Side. With more than 400 festivals each year throughout Chicago, the options can be daunting. Luckily, The Phoenix has narrowed the list down to six street fests to fill the summer days with music, food and entertainment.

Do Division Street Fest (May 31-June 2)

Running down Division Street, from Damen Avenue to Leavitt Street, Do Division Street Fest celebrates Chicago’s West Town May 31 through June 2 with local vendors, food, drinks, live music and family-friendly fun.

This summer fest includes two live music stages programmed by West Town’s renowned music venues, The Empty Bottle and Subterranean. This year’s music lineup will feature bands including WHY?, Russian Circles and The Cool Kids ranging in genres from rock to alternative to hip hop.

Local retailers and boutiques of West Town will participate as vendors. The festival also features Do Fashion, a series of fashion shows running throughout the weekend, complete with a runway and DJs.

A $10 donation is suggested upon entry and all proceeds benefit local schools and non-profit organizations. Do Division Street Fest will be open 5-10 p.m. May 31 and 12-10 p.m. June 1-2. More information can be found on the festival’s website,

Chicago Food Truck Fest (June 22-23)

The annual Chicago Food Truck Fest is back for the sixth year and welcomes foodies from around the city to enjoy everything from Asian street food to pierogis to a variety of sweet treats. Named one of the best food truck fests in the United States by Dream Vacation Magazine, the festival will feature a diverse, gourmet food truck lineup, including Piko Street Kitchen, Lobster Claw, Big Mama’s Kitchen, Fresh Off the Grill, Beaver’s Donuts and many more.

The festival will also feature Chicago’s best beer, since it has been named the new brewing capital of America for housing more breweries than any other city in the nation, according to the Chicago Tribune. Aside from food and drinks, Chicago Food Truck Fest will have games and live music for all attendees to enjoy.

Chicago Food Truck Fest will be located between 1600 and 1800 S. Wabash Ave., and will run from 11 a.m. to 8 p.m. June 22-23. General admission is free and tickets can be reserved online at

Chicago Craft Beer Fest (July 20-21)

Those 21 and over can enjoy what’s on tap at the Chicago Craft Beer Fest. Although the tasting selection hasn’t been announced yet, attendees will have the chance to enjoy craft beers from more than 35 local, regional and national breweries.

Ticket holders will have the opportunity to choose from more than 70 specialty beers and enjoy tastings, local vendors and music throughout the day. With the purchase of a general admission ticket, attendees will get access to the tasting area from 1-8 p.m., private tasting areas, live music and seating areas, as well as a souvenir tasting glass.

All tickets can be purchased, starting at $40 for general admission and $50 for VIP, which includes extra drink tickets, an exclusive tasting menu and early access to the tasting area. The Chicago Craft Beer Fest will take place on Lincoln Avenue, between Addison Street and Roscoe Street, and will run from 12-10 p.m. July 20-21.

Wicker Park Fest (July 26-28)

For the 16th year, Wicker Park Fest will celebrate the neighborhood with three days of live music, local food, a kid-friendly area, retail vendors and art. The fest takes place on Milwaukee Avenue, between Paulina Street and North Avenue.

Wicker Park Fest is a music-centric festival, with four stages and more than 40 artists. Subterranean partners with the fest in curating the music lineup and is one of the hosts for the Wicker Park Fest After Dark parties. The music lineup for 2019 isn’t yet available, but last year’s artists included Sir the Baptist, Reggae Gold, Porches and more.

Wicker Park Fest is located a short walk from the Division or Damen Blue Line stops and will run 5-10 p.m. July 26 and 12-10 p.m. July 27-28. More information about the festival and its lineup can be found on the Wicker Park Fest website,

Edge Fest (August 3-4)

Located in Loyola’s backyard, Edge Fest will bring local vendors, entertainment, food and family-friendly fun to showcase all the Edgewater neighborhood has to offer.

The music lineup and schedule are yet to be announced, but the sixth annual Edge Fest will feature local musicians and vendors, according to the event’s website, Edge Fest is pet-friendly and will host the third annual pet parade and elect the “pet mayor of Edgewater” for the first time.

Edge Fest spans one block down Broadway Avenue, from Thorndale Avenue to Ardmore Avenue. The festival will run 12-10 p.m. Aug. 3 and 12-9 p.m. Aug. 4.

Northalsted Market Days (August 10-11)

The 38th annual Northalsted Market Days is coming back to Boystown August 10-11. Spanning half a mile from Addison Street to Belmont Avenue on Halsted Street, this weekend celebration features more than 200 vendors, DJs and all-day lineups of live music on five stages.

The festival is open to all ages and a $10 donation is suggested upon entry. The music lineup will be announced in May, according to the festival’s website. Last year’s Northalsted Market Days featured artists such as Betty Who, Todrick Hall and 16 Candles, as well as DJs such as Tom Stephan, Oscar Velasquez and Toy Armada.

Northalsted Market Days is a short walk from the Addison and Belmont Red Line stops and will be open, rain or shine, from 11 a.m. to 10 p.m. More information and this year’s music lineup can be found on the festival’s website.

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