19 Ways to Celebrate Juneteenth in Chicago This Year

Here are the local events and festivities to help honor the holiday's indelible significance.


The longest-running African American holiday, Juneteenth, is quickly approaching, and here in Chicago, a host of parties and events will keep you celebrating all weekend long. Juneteenth, or Jubilee Day, Emancipation Day, Freedom Day, and Black Independence Day, for over a century has been a time of Black celebration in this country, but only last year was recognized as a federal holiday‚Ķ and it’s about damn time! The holiday commemorates June 19, 1865, the day troops entered Galveston Texas to ensure that every enslaved Black American was freed, though slavery had been abolished for over two years prior with the issue of the Emancipation Proclamation. The date is a harrowing reminder of our country’s past, and while the holiday does not shy away from that history, it is first and foremost a day to celebrate Black achievements, culture, joy, resilience, and pride. In Chicago, there are countless ways to celebrate from block parties and bike rides to parades and live music events. Here are 19 ways to celebrate Juneteenth this year.


Pedal through the streets to celebrate Black joy

Sunday, June 19, 11 am – 4 pm
200 S. Michigan Avenue
Nothing says community more than biking together for a purpose. The folks over at Black JoyRide, an organization that recognizes the mental and physical health benefits of biking, aim to get Black folks on bikes and this year’s organized ride is going to be a good one. The route will start on Michigan Avenue near Millennium Park at the former Johnson Publishing Building-the first African American-built structure in Chicago that held John H. Johnson’s influential African American publishing company-and make its way south to Hyde Park ending at the DuSable Museum where outside activities like grilling and music will be taking place. Bring a helmet, your sunglasses, water, snacks, and of course, your bike.
Cost: Free

Stay grounded with yoga and a sound bath

Sunday, June 19, 11 am – 2:30 pm
LuluLemon 944 North Avenue
How about starting your day with a little self-love before the Juneteenth evening’s festivities? Through Slo ‘Mo events, Chelsea McFadden will be leading a relaxation yoga practice with mats and blocks provided by LuluLemon at 11 am followed by a 1 pm meditative sound bath led by Tune in with Tristin. Both events will get you feeling tingly, nurtured, and calm.
Cost: $20 per class or $30 for both


Sip the night away at Moneygun’s Juneteenth Party

Sunday, June 19, 5 pm – late
Moneygun will be hosting a lively night of dance with music kicking off at 8 pm by DJ Police State. Plus, in the spirit of pride, the bar is donating $1 to Brave Space Alliance from each rotating specialty cocktail sold from their Monthlygun cocktail list. Drinking a cocktail and supporting a good cause? Yes, please.
Cost: No cover

Feel inspired by a dynamic musical

Friday, June 17, 1 pm – 3 pm and 6 – 8 pm; Saturday, June 18, 4 – 6 pm; Sunday, June 19, 7:30 – 9:30 pm
Vittum Theater
Highly respected producer, speaker, host, and professor Ted William III is behind this stunning two-hour musical theatre performance, 1619: The Journey of a People, The Musical. The show artfully portrays how generations of African Americans have fought for equality from the Great Migration to current social justice movements. Incorporating a diversity of musical styles from hip hop to jazz, and featuring a fantastic cast of dancers, actors, and singers, this show is designed to energize and inspire.
Cost: $35 – $69

Activate your endorphins at a 5k run

Saturday, June 18-registration starts 8:30 pm – 9:15 pm
Garfield Park
This is the second year that Peace Runner 773 will be hosting their Juneteenth 5k walk/run. Peace Runner 773 is a Chicago non-profit organization that advocates for health and wellness in Chicago’s west side through adult and youth programming. The 3.1-mile route will start near Garfield Park and end on the football field. After running, expect a wind-down accompanied by live music and community bonding. All proceeds will go towards Garfield Park Gators Youth & Football.
Cost: $10

Voice of the People Uptown Chicago
Voice of the People Uptown Chicago
Voice of the People Uptown Chicago

Party with your Uptown neighbours at a Jubilee Fair

Saturday, June 18, 11 am – 3 pm
Harry S. Truman
Non-profit organization Voice of the People, which focuses on affordable housing for Uptown residents, has organized this Juneteenth Jubilee and Community Resource Fair for the Uptown community. The Juneteenth fair aims to get neighbours and friends to congregate and celebrate the holiday through games, food, live music, and more. Proof of uptown residence is not required, so come one come all.
Cost: Free

DuSable Museum of African American History
DuSable Museum of African American History
DuSable Museum of African American History

Learn, eat, and play at DuSable Museum’s Juneteenth BBQ

Sunday, June 19, 11 am – 8 pm
DuSable Museum
The DuSable Museum and Chance the Rapper will be presenting a day and evening full of food, drinks, conversation, history, art, games, horseback rides, and special performances. Along with the festivities, the historic museum’s doors will be open free to all guests. Among the number of inspiring exhibits on display is the current Quilting Exhibition, a stunning quilt made by Melvina Young, a former slave. Whatever you do, don’t forget to BYOG (Bring Your Own Grill) for an epic community cookout.
Cost: Free

Soak up the entertainment at Douglass Park’s Village Fest

Saturday, June 18, 12 pm – 6 pm
Douglass Park
Back in 2020, the Village Leadership Academy students succeeded in renaming this park to Douglass Park to honour the work of Anna and Fredrick Douglass. This year Juneteenth Village Fest will be commemorating African Americans’ liberation from slavery by hosting festivities in the newly named Douglass Park through It Takes A Village Family of Schools (ITAV). The day will include entertainment from a main stage with a music performance by Ric Wilson, stand-up by Leon Rogers, dance by Redd’s Angelz with Hiplet Ballerinas, and magic by Spellbinder, to name a few. If that wasn’t enough, kid- and adult-friendly activities like free carnival rides, games, vendor booths, a petting zoo, face painting, and rock climbing, are bound to keep your head spinning.
Cost: Free

Dance it out at a Community Picnic

Saturday, June 18, 11 am – 5 pm
91st & Prospect
Celebrate Black culture, music, food, creativity, and more at this lively community picnic taking place in the beautiful Dan Ryan Woods. The event will include Back owned vendors, Black art, music, film, and child-centric entertainment. Also featured will be a set by DJ Jeff Da Illest, and live Afrobeat performances by Queen Drie, Jesse Nation, and Victor Coke.
Cost: $10 for adults and $5 for 18 and under

Take to the streets alongside Juneteenth icon Opal Lee

Saturday, June 18, 10 am
Starting at Robert Crown Center area lot in Evanston
At 95, Opal Lee remains one of the most influential Juneteenth organizers. Some even consider her the grandmother of Juneteenth. Her decades-long work organizing walks across the nation and her message that this holiday is about unity has helped push Juneteenth to be recognized as a federal holiday. This year, Chicago will host The National Opals Walk for Freedom campaign and is lucky to have Opal walking in our streets to celebrate the actualization of her work. Make a banner and head north to witness the icon herself.
Cost: Free. Pre-registration with donations appreciated.

Devote the whole weekend to the 1865 Fest

June 17 – 19, 11 am – 8 pm
Garfield Park
This three-day event held at Garfield Park has a lineup of family-friendly activities like live music, educational workshops, and no shortage of free food and good times. Highlights of the weekend include a flag-raising ceremony on Friday, educational workshops on Saturday, and a father’s day grill off with live musical entertainment on Sunday, Juneteenth.
Cost: Free

Listen closely to a book discussion

Thursday, June 16, 6 pm
If for some reason you can’t leave your house this weekend but still want to take part in the spirit of Juneteenth, the Chicago Public Library is hosting the event Voices for Justice Juneteenth Celebration, where writer, poet, and scholar, Clint Smith, will discuss his book, How the Word Is Passed: A Reckoning with the History of Slavery Across America. The event will be live-streamed through the Chicago Public Library’s YouTube channel and Facebook page.
Cost: Free

Get lost at an art exhibition celebration

Saturday, June 18, 6 – 9 pm
The Joy Room Chicago
When you’re looking for a calmer, more contemplative weekend event, abstract painter Victoria Slone’s exhibit, All That They Carried, seeks to stimulate conversations about the stories of those who were enslaved in the United States and honour their legacy. All proceeds from the exhibit will be donated to the Chicago Alliance Against Racist and Political Oppression.
Cost: $5

Let loose at a block party

Sunday, June 19, 12 pm – 10 pm
The Woodlawn
The Woodlawn is hosting a Juneteenth Block Party this year, and it is going to be jam-packed with activities like an adult dance class, father’s day tournament, comedy showcase, talent search, DJs, prize competitions, local vendors, photo booth, karaoke, and more. In the evening, the celebration will continue with an adults-only party with live music and drinks.
Cost: Free

Spruce up for the Emancipation Ball

Saturday, June 18th, 7 pm – 11 pm
99th Floor of Willis Tower
If you’ve been looking for a reason to get fancy, don’t hesitate to grab tickets to this inaugural Emancipation Ball organized by Moor’s Brewing Co. and Disb…ôlńďf Tequila. The black-tie event will have a special appearance from Chicago Bear’s reporter Herb Howard, and music by DJ Sean Mac and DJ Bamn. The ball will have an open bar, hors d’oeuvres, a Black art exhibition, a spectacular sunset view, and a fireworks display. There will also be a collective toast to excellence because, of course.
Cost: $150 – $400

Chicago Tap Theatre
Chicago Tap Theatre
Chicago Tap Theatre

Groove with M.A.D.D Rhythms

June 19, 1 – 5 pm
Harold Washington Cultural Center
This event is sure to get you in the mood to celebrate Juneteenth with a lineup of live dance from M.A.D.D Rhythms, Chicago Tap Theater, Blu Rhythm Crew, and The Happiness Club. To boot, the event will also have workshops, raffles, art, and complimentary food.
Cost: Free

Spend your dollars at local Black-owned businesses

Sunday, June 19, 2 pm
The Promontory
The Promontory in Hyde Park will be hosting a Black-owned business pop-up market where vendors will be selling many items from clothing, beauty products, art, and more. Make sure to come hungry as there will be a lineup of food vendors dishing out their specialties.
Cost: Free

Celebrate your dad too at this Lawndale Juneteenth kickback

Sunday, June 19, 4 – 9 pm
3200 W. Douglas Boulevard, between Kedzie and Albany
Bring your dad to this kickback-style Juneteenth and father’s day celebration in Lawnsdale hosted by Light Up Lawndale. If you’re the competitive type, you’ll be excited to know that there will be potato bag sack races, double dutch contests, hopscotch, and hula hoop contests. More laid-back activities include live music, a mini car show, and DJ appearances.
Cost: Free

Congo Square Theatre Company
Congo Square Theatre Company
Congo Square Theatre Company

Paint your face and pet a lizard at UCAN’s celebration

Saturday, June 18, 11 am – 3 pm
UCAN’s Drost Harding Campus
This UCAN Juneteenth celebration will uplift the lives of our Black community through a round-up of undeniably fun kid (and adult) activities like chess games, a waterslide, reptile petting zoo, face painting, and a bounce house. There also will be performances by Congo Square Theatre, Celestial Ministries Drum Line, and community storytelling. Local vendors will be selling everything from body care, and books, to barbecue and soul food.
Cost: Free

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Elanor Bock is a Chicago born, New York-based professional dancer, writer, and renaissance woman, excelling at philosophy, mathematics, outdoor adventuring, and balancing six martinis on a tray in a crowded bar. Like her dog Oli, she is highly motivated by treats. Follow her on Instagram @rathernotthanks.


Robyn DaCultyre Is Doing It for the Culture

"The cool thing about Ohio is that there is literally a place for everyone."

Photo by Kayode Omoyosi
Photo by Kayode Omoyosi
Photo by Kayode Omoyosi

I was introduced to Robyn DaCultyre at an Untitled Queen show at C’mon Everybody in late January, and it was one of the most unique drag shows I’d seen in a while. Afterwards, I tracked down this self-described “drag creature” and video chatted about her drag origin story, the state of drag in her native Ohio, and the dual identities that make up her persona. Thrillist: I want to ask you about how Robyn DaCultyre came about and your point of view behind your performance.

Robyn DaCultyre: I’ve been travelling around the country from a young age in ministry and Christian studies. I moved to Chicago right after high school. Four years later, moved back to Columbus and decided I didn’t really want to do church anymore; that wasn’t where my heart was.

I had a really low point in my life and had a suicide attempt and then really found drag and started doing drag as a coping mechanism and way to let off steam. I started in July of 2019, and it was really a lot of punk and metal music. I created this drag creature of sorts and they were really out of this world and celestial and all of those fun alien type terms.

And then we went into a global pandemic and I had a lot of time to figure out who I wanted to be. Digitally I was still doing a lot of drag creature-esque numbers and all of that, but I had this moment where we’re on the front lines getting hit with pepper spray and rubber bullets and pepper spray-all of those lovely things. And I said, I have this platform and I need to start showcasing what’s happening.

Untitled [Queen] stepped in at the right time and messaged me and said, “I’m doing this show for Independence Day called Untitled in America with 52 different performers and I want you to be a part of it.” It was at that moment I was able to take the footage I had been recording on the front lines and incorporate it into digital content. I did a song called Black Like Me by Mickey Guyton that talks about white picket fences, but if you want to see how America is, then you should try being Black like me. The imagery of what’s literally happening in Columbus in that digital performance really spearheaded me into focusing on people who look like me.

Nina Simone is one of my biggest inspirations, and one of her quotes that resonates with me is that it’s the duty of the artist to resonate with the times. My art is politically charged. I like to entertain, but there will definitely be a time when you come to a show expecting to have your drink and be chill and that might not be the case.

How did the name Robyn DaCultyre come about?

I was smoking with Ursula Major, who was on season one of Dragula, and the first time I introduced myself to her I was Robyn Banks, which is my drag name originally. She said, “Well, do you just not want to be original at all?” [Laughs] And I sat with that for a couple of months, and I got really stoned one day and was listening to Janelle Monae, and she talks about doing it for the culture, and I said “I do it for the culture, too!” And the rest is history.

And you started a series called Melanated.

We started Melanated last February. I told the idea to my show director that there were no shows specifically run by Black people that only featured Black entertainers. I wanted to do this show for a night and she said, Why don’t we do it once a week for the whole month? The first show happens, and it’s a sold out crowd, and [my director] comes back and says we should do this every month. So I sucked it up and here we are a year later.

Melanated is the only fully Black show in all of the state. It’s a horrible marketing tool and not something I want to promote, but it is just a fact. It amazes me that we are the 13th largest city in America and there’s nothing here that’s fully focused on Black entertainers. The name also comes from Janelle Monae; she says she’s highly melanated and I said, that works.

Photos by Chay Creates LLC (left) and Bridget Caswell (right)
Photos by Chay Creates LLC (left) and Bridget Caswell (right)
Photos by Chay Creates LLC (left) and Bridget Caswell (right)

You refer to yourself as a drag creature, as opposed to drag queen or king…

This is actually the first time I’m making this public. I am in this place where I want to separate the alternative creature from who this melanated goddess or whatever is. DaCultyre is definitely the person who runs Melanated and then Robyn is this drag creature that is out of this world and really loves punk and alternative music. And both intertwine to make Robyn DaCultyre.

You also do pageants. Tell me about that.

In 2020 I was appointed by Nina West, who is from Columbus, as the representative from Ohio for National Entertainer of the Year in Louisville, Kentucky. I placed ninth out of 13 contestants and I really fell in love with the system and fell in love with the pageantry and loved the idea of reigning and being different. I want to show that we as alternative performers, as bearded performers, you can come into these systems and shake things up.

Is there a uniquely “Ohio” style of drag?

No, and I think that’s one of the things that makes it so amazing is that everyone has their own unique style, and it’s all pretty much accepted. I started as a performer and a drag creature and there was space that was afforded to me and I transitioned to more glamor and pageantry and that’s afforded to me as well. I’ve been a bearded entertainer for a year now. The cool thing about Ohio is that there is literally a place for everyone.

I think I have everything I need. Is there anything else I didn’t ask you about that you want to bring up, or‚Ķ

I don’t think so. Are there any generic questions you haven’t asked?

Generic questions‚ĶI think I asked all of them already [laughs]. I like to ask what you’d be doing if you weren’t doing drag?

It’s a great question. I have a day job that is very demanding so I need drag to get away. I’m also very creative and artistic. I used to do web design and all these other things to pull into my creativity. Drag is the longest thing I’ve stuck with in all parts of my life, so I don’t think it’s going anywhere anytime soon.

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John deBary¬†is a drinks expert and writer. His first cocktail book,¬†Drink What You Want, is available now, and his next book,¬†Saved by the Bellini, is expected in early 2023. He is also the co-founder and president of the¬†Restaurant Workers’ Community Foundation, which is dedicated to improving the lives of hospitality industry professionals through advocacy, grant making, and impact investing.


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