10 Actually Fun Things to Do in Chicago This Weekend

Honor Juneteenth, celebrate dad, and raise a glass to summer in the 312.

Virtue Cider
Hilton Chicago Great Hall | Virtue Cider
Hilton Chicago Great Hall | Virtue Cider

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



Weekend plans change fast, so grab a drink that’s ready when you are. Tanqueray’s Crafted Gin Cocktails come ready to drink and are the perfect addition to any occasion. Made with real Tanqueray gin and natural flavors, they deliver premium, bar-quality cocktails whenever you want. Grab a can and enjoy.

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
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
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

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Jay Gentile is an award-winning freelance journalist specializing in travel, food & drink, culture, events and entertainment stories. In addition to Thrillist, you can find his work in The Washington Post, The Guardian, CNN Travel, Chicago Tribune, Lonely Planet, VICE, Outside Magazine and more. Follow @thejaygentile.
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