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Guide to Chicago's 2019 Summer Streetfests

By Ji Hee Choi and David Miotto

Posted: Friday, May 17, 2019

With summer approaching, Chicago’s annual neighborhood street festivals will be in full swing. Over the months of May, June and July, Chicago will be bustling with the many food festivals, beer gardens, music acts, parades and other event that fill the neighborhoods all over the city.

Although there will be many things to do for everyone, Chicago’s neighborhood street festivals set themselves apart by keeping long-standing traditions alive and bringing many communities together.

Chicago’s neighborhood street festivals offer local bands, DJs, arts and crafts, games and performances. In addition, many vendors offer local products ranging from paintings and pottery, to T-shirts and jewelry. 

The month of May will bring festivals such as Mayfest, Belmont-Sheffield Music Fest and the Lincoln Park Wine Fest to life. Chicago’s Mayfest kicks off the summer festival series. Located in Lakeview on 3100 N. Ashland Ave., this festival runs from May 17 through 19.

This year, there will be plenty of live entertainment for all to enjoy. Local bands, such as, Too White Crew, Sixteen Candles, and 7th Heaven, come out to preform; providing plenty of jams for everyone to dance to.

Many of Chicago’s neighborhood street festivals can take quite a bit of planning. Local event planning company Star Events, has made a name for themselves in Chicago by being the main force behind many of these neighborhood festivals. These festivals include, Mayfest, Spring Awakening, Andersonville’s Midsommarfest, Taste of Randolph and many more.

Planning these festivals is far from being an easy task, and Star Events’ own event coordinator Meredith Mackey can attest to it.  It requires booking musical entertainment or performers, getting all the right vendors in place, the execution of the event, and much more. These local festivals feature hundreds of vendors, and Star Events has been working with some of them for a long time.

“We plan year round for all our events, our office works year round in all of the events trying to get everything organized and coming up with new processes to add to our events, so we work year round,” she said.

Mayfest 2018. (Photo/WikimediaCommons)

“We have a lot of returning vendors that have been with us for years and years, some have been with us for over 20 years and those are tied and true to us” Mackey said. Star Events also tries to innovate and add new vendors to their regular lineup.

She added, “We solicit vendors that we find at other festivals that we think are cool. We are excited to have new people in the mix too.” The main challenge behind the planning of all these street festivals, is the challenge of problem solving.

“If you are off site, there can be six different vendors showing up at the same time at 6 a.m., and they all want the same space, but they were all assigned different spaces. So there’s a lot of problem solving challenges that comes with planning these street festivals” Mackey added.

Despite that many challenges that can arise in the planning of some of these street festivals, Star Events seeks to deliver customer satisfaction in both ends of the spectrum.

“We make sure that everyone is happy as they can be, we are a customer service based organization, and want to make sure that our vendors are in the best possible position to do well over the weekend,” she said.

Although there are many neighborhood street festivals in Chicago during the warm weather season, some of them have a different kind of feeling, and have plenty of community involvement from their residents. A great example of this is the Old Town Art Fair.

Taking place, this year on June 8 and 9, this art focused festival will feature 250 artists, live music, a garden walk, and a kid’s corner amongst many things. The event is celebrating its 70th fair this year.


Old Town Art Fair, 1968. (Photo/WikimediaCommons)

The history of the Old Town Art Fair goes back to the years of World War II, and co-chair of the communications committee, Nancy Jordan, shared some insight on this festival’s beginnings.

“It started out as an alley book sale, people used to sell used books on the alley here, and then people started bringing objects, and during the war they made things to sale, and it gradually became an art fair,” she said.

The Old Town Art Fair relies heavily on community involvement. “It’s all volunteer work, so you have to get a lot for a little bit of money, you don’t have a lot to spend so you have to get the word out to put the fair on and get sponsors, it’s all volunteer work, because it’s a non-profit” Jordan added.

In the end, the neighborhood of Old Town benefits from this because like Jordan said, “all the money goes back to the community, to the schools, and homeless centers.”

Creating a strong bond amongst the community is key in the making of this festival. Sue Pajakowski, who works in the promotions committee for the fair said that, “last year we had over 600 volunteers, we get a lot of volunteers that support the flag community.”


Old Town Art Fair 2019 Poster Photo: David Miotto

In order to find not just local, but nationwide talent, the committee takes applications from artists all over the country. Been a juried art fair they have different categories for the awarded prizes. “They pick two in each category, so it might be sculpting and oil painting, and they have winners and a monetary prize” she added.

This year the Old Town Art Fair has added something new to their lineup of musical guests and activities.

“We are going to start a tour called, the art insiders art tour, and it’s to take our really serious art buyers, on a kind of a back, you know seeing tour of 10-12 artists and really let them get the inside scoop from some of these artists, about if some of the them would be returning artists, or some of them would be new artists” Jordan said.

In festivals such as this one, the concept of community really matters. “Everybody just helps out every year, and a lot of people have lived in Old Town for a long time” Jordan added.

Neighborhood Festivals

As far as local neighborhood street festivals goes, there’s a little bit of everything for everyone, from Roscoe Village Burger Fest, to North Halsted Street Market Days, to the Taste of Greektown. So if you decide to venture out this year and go to one of them, don’t limit yourself, as there are plenty of options for all partygoers to enjoy. Be sure to check out more than one festival.


Mayfest takes place May 17 through 19, and its main stage is set up under a big-top tent, and features some of the best (ice cold) beverages such as Bloody Marys, Vodka Lemonades, and of course, a variety of beer selections. This event, based at the corners of Leland and Lincoln avenues, is known for showcasing some of the best music, entertainment, and festival food in all of Chicago.

Belmont-Sheffield Music Fest

This popular Memorial Day weekend party takes place on Sheffield Avenue in the bustling Lakeview neighborhood just steps from the Belmont El station. Top local tribute bands on the main stage (near Roscoe), food, drinks, artisans and dancing. The second stage will be featuring entertainment booked by neighborhood venues are on tap for this 35th annual event.

Lincoln Park Wine Fest

After Chicago’s brutally cold winter, spring’s warm breezes will be a welcome relief when the Lincoln Park Wine Fest with it the glorious grapes, along with smooth tunes, artisans and tasty edibles, takes place on May 17 through May 19. Lincoln Park Wine Fest will again transform the tranquil two-acre Jonquil Park into an open-air market featuring wine and food pavilions. The highlight is ticketed wine tastings where scores of varietals will be showcased. 

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