Although music festivals are fan favorites during the summer, businessman Jonathan Swain is always cognizant and careful of the negative effects that such large-scale events may have on a community. As a Hyde Park resident, he’s always thinking about public safety, land damage, post-event cleanup and overall disruption to the public as he plans for the Hyde Park Summer Fest.

As the founder of the Hyde Park Summer Fest, Swain wants to make sure that the benefit of this festival, and its positive impact, far outweighs the disruptions that other festivals held in residential areas have naturally caused. As in previous years, a portion of the 2023 Hyde Park Summer Fest’s ticket sales will be donated to local CPS high schools; that amount will be matched by Bowa Gives, the charitable arm of Bowa Construction. Tickets are on sale here.

”So we’re approaching this as being neighbors to our neighborhood, and trying to provide benefits for our neighborhood,” Swain said. “So communities are always at the heart of what we’re thinking.” 

The Hyde Park Summer Fest will return to Midway Plaisance on June 17 and 18, serving a crowd for the whole family, with a lineup of artists ranging from gospel musician Jonathan McReynolds to “Don’t Play with It” breakout rapper Lola Brooke. On the first night, festival-goers will witness a line up that features 2 Chainz and a special performance by Clipse. 

And to celebrate 50 years of hip-hop, the festival’s second day will feature performances by some of Chicago’s rap pioneers like Twista, Do or Die, Shawnna and Crucial Conflict. The headliner for Sunday night will be one of the most influential female rappers, the legendary Lil’ Kim.

Formerly known as the Hyde Park Brew Fest, the festival started out in 2014 as a craft beer sampling event in a parking lot in Hyde Park. In 2016, it turned into a street festival, taking over 53rd Street with crowds of more than 25,000. In 2022, the Summer Fest moved to Midway Plaisance Park and became a two-day festival with major artists on the lineup. 

The festival is a staple of summertime Chi. With Black Chicago consistently being a target of negative headlines in mainstream media, the Hyde Park Summer Fest is a moment to celebrate the South Side, according to Swain.

“Ultimately, we’re trying to celebrate Chicago, we’re trying to celebrate what we think is the best of Chicago that sometimes gets overlooked,” he told The TRiiBE.

This interview has been edited for clarity and length.

The TRiiBE: What is your role with the Hyde Park Summer Fest?

Jonathan Swain: I am the founder of Hyde Park Summer Fest. It started in 2014 as the Hyde Park Brew Fest, and it evolved from a craft beer sampling in a parking lot in Hyde Park to a street festival that eventually took over 53rd Street. And then in 2022, we evolved into a ticketed music festival. And we also changed the name from the Brew Fest to the Summer Fest. I brought on folks like [creative director] Dave Jeff early on to help grow [and build] the brand. And then most recently Nosa Ehimwenman from Bowa Construction has also helped us grow into what has become the Hyde Park Summer Fest.

Black joy on display at the 2022 Hyde Park Summer Fest. Photo by Mike Hicks for The TRiiBE®

This year's festival is in celebration of 50 years of hip-hop. You guys have secured Chicago greats like Shawnna, Twista, Do or Die and Crucial Conflict. Why was it important to include these Chicago legends in this celebration?

It’s an important time for celebrating the 50th anniversary of hip-hop. It’s an important time for celebrating culture and celebrating growth. And when you think about Chicago, generally with the music, sometimes Chicago gets passed over. Think about where the anchors of music are: LA, New York and even Atlanta to some degree. And so we thought it was important as a part of the celebration that we honor Chicago hip-hop.

What goes into planning the Hyde Park Summer Fest these days? How's it different from planning back when it was the Brew Fest?

That’s a great question. So when we had the Brew Fest, we effectively could plan it in three months and execute an event. As the event grew, that three months turned into four or five months, [then] six months, and [then] eight months into nine months. And now this is a year-long planning process. It’s an orchestrated dance that balances a lot of different stakeholders and a lot of different interests to bring this together: the Chicago Park District, the City of Chicago, the Park Advisory Council and the Midway Park Advisory Council. In this case, we’re talking about the University of Chicago, whose property surrounds this strip of public land that’s in between it. It’s about talking to those folks and making sure that they’re on board, can support what we’re trying to do, and can believe in the vision of what we’re trying to accomplish. 

On the production side, it’s about securing artists, it’s about building and doing stage production, doing otherwise larger production [such as] food vendors and merchant vendors, security and all these different pieces. We’re happy to have support from our stakeholders, the Park District, and community members and all around. Ultimately, we’re trying to celebrate Chicago, we’re trying to celebrate what we think is the best of Chicago that sometimes gets overlooked. We’re trying to highlight Hyde Park, bring shine to Hyde Park, bring shine to the South Side, let people know that the narrative that’s put out there about the South Side is not the true narrative, that we understand what the true narrative is and that’s where we want to celebrate.

This lineup caters to mostly Gen Xers and Millennials with acts like Clipse, 2 Chainz and Lil Kim. Then there's Lola Brooke, whose audience trends a lot younger. What goes into choosing the headliners and other artists on the bill?

It’s a collective effort among all the partners and team folks who start talking about what kind of vibe we want to have this year. For example, [with] Chicago hip-hop, we want to make sure we celebrate that. [We’re] adding Jonathan McReynolds, a gospel artist, for the first time to open us up because you know a lot of folks love gospel music and that’s a part of the culture in a real significant way. [We’re] adding Robert Glasper, who is a jazz artist, but he’s also well involved in the hip-hop community. 

We wanted to give a really good mix where everybody could find their place. We also have to be mindful [of] wh’’s touring and not touring. After going through that, we come together with a lineup that we’re really excited about.

The Clipse are coming together for a historic headlining performance this year at Hyde Park Summer Fest. A lot of us Millennials have never seen them perform together in Chicago. How did you guys get this to happen?

Look, Chicago, I’ll say it this way, man: God smiles on us. That’s ultimately what it is. We were fortunate enough to have a lot of good relationships with good folks who can make connections for us. It all came together organically and we’re grateful to have them.

Black joy on display at the 2022 Hyde Park Summer Fest. Photo by Mike Hicks for The TRiiBE®

You also recently announced Lil' Kim as Sunday's headliner. She’s a legend in her own right. Sunday is also going to be the day we celebrate our Chicago hip-hop legends. Some, like Twista, are very active in the community. Did you feel a need to get an unfamiliar face for Sunday's lineup to attract a bigger audience?

I don’t think it’s a question of getting an unfamiliar face, per se. It says we are trying to build the best lineup we can with the best vibe we can. And obviously we’re celebrating 50 years of hip-hop again. And you know, Lil’ Kim, was the first to do what she does. I mean, you know, before there was a Cardi, there was Lil’ Kim. Before there was Nicki, there was Lil’ Kim. Before there was Meghan, there was Lil’ Kim, right. And so it’s about, you know, celebrating the work she’s done and the discography the catalogs she’s put together and really bringing in an iconic, iconic performer to Hyde Park. That’s really what we were focused on.

So some people complained last year about the change from the Brew Fest to the ticketed Hyde Park Summer Fest format. Logistically, how did the change in formatting impact the event and could you speak towards if it helped or hurt?

Well, I think with every business, because this is a business you have to evolve with time and they have to evolve and grow. And when you think back to 2019 on 53rd Street, we had basically restock capacity. We cannot go further down the street because of where the Sophy Hotel was, without going into a whole lot of minutiae. Because of the post placement of Sophy Hotel, it made it hard for us to cross Dorchester to extend the street so we had to begin rethinking how we’re gonna grow and sustain. And so when COVID-19 hit, it gave us an opportunity to rethink about what sustainable looks like for this business. 

And so after having given some serious thought, the pivot to a ticketed music fest effectively allows us to be much more sustainable over time, and we recognize that everybody doesn’t like change. And we could have done a better job explaining what the change was. But I think when people got to the event, and they saw that we were kind of building a campus on the Midway that had, you know, upgraded production and we had, you know, nationally known artists, I think people would appreciate that difference

Tell me about the initiative to give back to the nearby schools. And also on May 17, Hyde Park Summer Fest will be hosting a community showcase at The Promontory where local talent will perform with hopes of winning a slot to perform at the Summer Fest. Can you tell me just a little bit more about this?

Let’s talk about the second part first. When I talked about listening, that’s part of the listening that we did. One thing we heard last year is “hey, look, man, this is great. But where’s the slot for local talent?” So we added two stages to create more space for local talent to be able to get on the bill and be able to perform, and oftentimes we want to create space for people to have the opportunity to shine and to grow. And so this community showcase is directly related to some of the feedback that we got last year. And so we’re excited to see what Chicago has to offer when it comes to those two slots, one on Saturday and one on Sunday. 

Now, with the schools. So when you do an event like this, in any event, large-scale event, there are costs to communities. Okay, there’s disruption; any large scale event, the goal of the organizers should be to minimize the disruption as much as possible, and provide as much benefit as possible. So the give back to the schools that we did with Bowa Gives, is a function of us trying to create as much benefit as we can to creating temporary jobs, we create a benefit. 

By supporting small businesses, most of our vendors are either Black and brown food vendors or retail vendors, we were looking to provide significant benefits for our community. Partnering with Bowa Gives, you know, one of their missions about, you know, education, exposure experience, art, culture, music, STEM. You know, I had my  oldest two children graduate from Chicago Public Schools. And one thing I recognized was that different schools in different neighborhoods can raise money differently, depending on the economic base of the parents. Schools in the South Side may not have the economic base. And so we can provide an opportunity to give your dollars to those schools to help them do at least something to promote the programs to help young people, we thought it’d be a great thing to do. We also gave some money to local nonprofits, like the Blue Gargoyle to help them do work this year.

And we’re going to give away grants to local nonprofits, working with Scott Community Trust to help us do that. We’re gonna pick out, you know, some established nonprofits and also some grassroots nonprofits. We want to provide the support that we can through this economic engine that we’re creating so that our young people continue to benefit, thrive, shine, and can continue to produce the kind of things that produced us as we came up in Chicago.

How does that make the Hyde Park Summer Fest different from many of the other festivals that take place in Chicago?

Well, everybody does things differently. You know, we approach the festival a little differently, I think, than some other folks because, you know, I live in Hyde Park. You know, Dave’s brand literally means I Love Hyde Park. Nosa lives in Hyde Park, we’re neighbors. And so we’re approaching this as being neighbors to our neighborhood, and trying to provide benefits for our neighborhood. So communities are always at the heart of what we’re thinking, [and] what we’re doing. It’s just an extension of us thinking about this being a community. Is it a business venture? It absolutely is? Do we need to be successful in that business venture? We absolutely do. We need to be good stewards of that. Absolutely. But you can do well [monetarily] and do good at the same time. 

Without the community involved they might start to push back like what we’ve experienced with Festivals recently like Riot Fest, which is held every year at Douglas Park on the West Side. You know, they take over the park, and then there’s really nothing done to benefit the area.

And I can’t speak to what they do or how they do it. All I know is that we want to focus on listening, on providing benefits and to make sure the benefits of what we do outweigh the cost or to mitigate the disruptions. We want to make sure our benefit outweighs that. And we want to make sure we keep listening to what the community is saying and keep growing from that. For example, one of the things we heard last year was we need to do better with our ADA accessibility. So we’re doing more with our ADA accessibility. 

We heard that our VIP experience needs to be improved. We’ve improved our VIP experience this year. We’ve heard that we need to do a little better getting people in, so the lines were not as long. We’ve changed the whole process to make sure people are able to get in a lot faster. So there are a lot of things we’ve been doing and listening to. Even with respect to the park right, the people were concerned about how long it took to repair the park. We’re changing our process with that to make sure that we have to repair the park quickly so people can get back to using it shortly after the fest. But as part of the community, look, I have to see these folks, you know, who are concerned every day walking around the neighborhood. So we want to make sure that we do right by them. And because you know, we want to be treated the same way as being neighbors.

Any surprises in store for the festival that you can share? Anything exclusive that you can share with our audience?

Might have one, two more announcements coming. But nothing I’m able to say at this point. But I mean, ultimately, I think we’ll collectively build a solid quality event on the South Side of Chicago, where we can take advantage of the benefit and the whole city can take advantage of the greatness of the South Side of Chicago. You know, you don’t have any idea how many times I’ve heard people come down and say, I’ve never been down this way. I’ve never been here before. This is a part of your city, our city, right? And so we’re just excited by this opportunity to bring folks to the Midway in the shadow of Rockefeller Chapel. Really celebrate music, celebrate culture, celebrate community, celebrate hip-hop, celebrate foods and celebrate all that is the best of what Chicago has to offer so that again, the narrative that we hear around the world, we can continue to dispel so that people know what Chicago is really about.

is a culture correspondent with The TRiiBE.