10 Actually Fun Things to Do in Chicago This Weekend
Honor Juneteenth, celebrate dad, and raise a glass to summer in the 312.
Congratulations Chicago, it’s almost officially summer. (You remember summer, right?) And summer solstice weekend 2021 is wasting no time making the most of it. From Juneteenth rooftop parties and Pride Week performances to Father’s Day BBQs and weekend craft beer festivals, one thing you won’t be this weekend is bored. Here’s everything fun you can do in Chicago this weekend.
Get juiced at the grand opening of new West Loop wine shop Juice 1340
Saturday, June 19
Juice 1340
South Side sommelier and Wine Enthusiast 40 Under 40 Tastemaker Derrick C. Westbrook officially opens his highly anticipated new wine, beer, and cocktail shop on Juneteenth. The outpost also includes a bar area and event space, as they plan to host educational events and tastings.
Cost: No cover; beverage prices vary
Support Black-owned businesses at a Juneteenth market
Friday, June 18 - Sunday, June 20
Various locations
On Friday, The Ace Hotel’s Freedom Market will feature a curated selection of more than a dozen Black-owned local businesses showcasing a variety of goods from clothing and art to plants and wellness products, with a live DJ and a percentage of proceeds going to charity. On Saturday, The Promontory’s Black Mall is putting on their own marketplace with Black-owned vendors hawking all things fashion to beauty alongside food vendors. Then on Sunday, The Promontory hosts The Black Market outdoor fundraiser and flea market featuring Black-owned businesses and creatives plus donations for charity.
Cost: Admission, shopping, and food and drink prices vary
Stroll the street with beer in hand at the Chicago Craft Beer Festival
Friday, June 18 - Sunday, June 20
Peoria Street from Fulton to Lake
Celebrate the official start of summer with this street festival-style event taking over the West Loop with a bevvy of offerings from Midwest brewers plus live music and a pre/post-party at PB&J West Loop.
Cost: Admission runs $30 per session
Head out to the farm for Virtue Cider’s Father’s Day Weekend BBQ
Friday, June 18 - Sunday, June 20
Virtue Cider
Get out of town and road trip it over to Virtue Cider’s Fennville, Michigan farm for a weekend of grilled bites, popsicles, and live music from The Bootstrap Boys on Saturday as part of Virtue’s Hideout-curated Farm Sound series. Oh—and hard cider. All the hard cider.
Cost: No cover; menu prices vary
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Hang with Barack and Michelle at the unveiling of the Art Institute’s Obama Portraits
Friday, June 18 - Sunday, August 15
Art Institute of Chicago
Chicago is the first stop for this five-city tour organized by the Smithsonian’s National Portrait Gallery, with portraits of Barack and Michelle Obama available for viewing at the site of the couple’s first date.
Cost: Free with museum admission (prices vary)
Show your colors at The Northman Riverwalk’s Pride Week Launch Party
Friday, June 18
The Northman Riverwalk
Make your way down to The Northman Beer & Cider Garden’s Riverwalk location for this Pride Week kickoff event featuring a special performance from Mercedes Tyler along with Belvedere drink specials.
Cost: No cover; menu prices vary
Watch the Evanston Juneteenth Parade before checking out Evanston’s newest venue
Saturday, June 19
Various locations
After watching Evanston’s Juneteenth Parade & Celebration make its way from the Robert Crown Community Center to Ingraham Park—where there will be live performances, muralists, and street vendors—head over to the post-parade grand opening of Evanston’s new 10,000-square-foot music and event space PALMHOUSE for their Palmhousepalooza event with live music, art installations, games, food, cocktails, and more.
Cost: Parade is free; Palmhousepalooza tickets run $10 per person
Party on the rooftop at The Woodlawn’s Juneteenth Block Party
Saturday, June 19
The Woodlawn
The Woodlawn’s second annual Juneteenth Block Party features an open bar on the rooftop patio plus DJs, small bites, and a bottle of your choice with table reservation. That’s a win-win in our book.
Cost: Admission starts at $50 per person
Catch up on some local metal at Reggie’s Chicago Metal Fair
Saturday, June 19
Reggie’s
Lose yourself in all the amazing local bangers that came out during the past 15 months of lockdown at this event popping up on the second floor of Reggie’s with food, drink, merch, and new music releases.
Cost: No cover; menu prices vary
Show off your Golden Tee skills at Lottie’s Father’s Day US Open
Sunday, June 20
Lottie’s
All those hours spent playing Golden Tee in dive bars finally pays off this weekend as Lottie’s hosts a Golden Tee Hole in One Tournament to win a golf bag and other prizes along with beer bucket, whiskey, and burger specials. Consider Father’s Day covered.
Cost: No cover; menu prices vary