From Friday through Sunday, we know you don’t even want to think about work but rather looking for a fun distraction to occupy your weekend in the city, help is here. Whether you want to explore new haunts in Chicago, relax, take in a festival, or have a night out on the town that’ll make your snapchat and insta stories followers green with envy, here’s what to get into this weekend. It’s #summertimeChi so there’s a lot taking place this weekend but these are the recommended ones for you to go either solo or with a group for a good time. The Chicago Weekend Guide for June 28-30.
FRIDAY JUNE 28
WHAT :: Chicago Is A Drag Festival

WHERE :: Cheetah Gym back lot| 5248 N. Clark Street
WHEN :: Friday, June 28
WHY :: “Chicago is finally getting the epic drag festival it deserves with a star-studded pride event” raves The Block Club Chicago. The event organized by A Queer Pride group is the first outdoor drag fest in the Midwest and will feature special guests including Tiffany Pollard, Candis Cayne, TS Madison, “RuPaul’s Drag Race” star Raja and Chicago icons like Lucy Stoole who will serve as one of the emcees. The festival will also honor the 50th anniversary of Chicago’s first Pride Parade and will feature tributes to iconic members of Chicago’s drag and queer communities.
COST :: Tickets start at $25 | Click here for more info
WHAT :: Logan Square Arts Festival
WHERE :: Logan Square | 2620 N. Milwaukee Avenue
WHEN :: Friday June 28 – Sunday June 30
WHY:: Celebrating its 10th Anniversary this year, the Logan Square Arts Festival is a three-day celebration of the diversity and vitality of Chicago’s Logan Square neighborhood, one of the most iconic green spaces in the city of Chicago. The festival features two stages of live music, visual art, performance art, dance, food, and drinks, in the heart of Logan Square. In 2018 over 30,000 people celebrated the first weekend of the summer on Logan Square. The LSAF Afterparty on Friday will take place at East Room starting at 10pm.
COST :: $5 suggested donation | Click here for more info here
WHAT :: Sangria Fest on the Beach
WHERE :: Shore Club | 1603 North Lakeshore Drive
WHEN :: Friday June 28
WHY:: Taste a variety of sangrias while hanging out at Shore Club on North Avenue Beach! Tickets include 3 hours of sangria tastings, giveaways & MORE!
COST :: Tickets start at $35 | Click here for more info here
WHAT :: Armchair Expert Live With Dax Shepard
WHERE:: Chicago Theatre | 175 N. State Street
WHEN :: Friday June 28 | 8PM
WHY:: Actor and comedian Dax Shephard brings his popular podcast to the stage. With its special guests, the show journeys with its subjects from how they were shaped in childhood to the moments and milestones of adulthood that have defined their careers and lives. “Armchair Expert is, according to Dax himself, a celebration of the messiness of being human.”
COST :: Tickets start at $68.50 | Click here for more info
WHAT:: Afro Beats in Hyde Park
WHERE :: The Promontory | 5311 S Lake Park Ave W
WHEN :: Friday, June 28 Doors at 10:00 PM
WHY :: Experience the sounds of Afrobeats dancing the night away with DJ Dee Money, DJ Three K, & DJ Matrix.
COST :: Early Bird – $15; Limited Free w/ RSVP before 10:30pm | Click here for more info
SATURDAY JUNE 29
WHAT:: MCA Chicago Presents Prime Time: “Question Everything”

WHERE :: MCA Chicago | 220 E. Chicago Avenue
WHEN :: Sat, Jun 29, 2019, 7–11 pm
WHY :: Influenced by Virgil Abloh’s “question everything” ethos, this after hours museum takeover features performing artists, local designers, and live music, DJ sets, and more. Browse item from Pop-up stores from Chicago designers Sheila Rashid, Brandon Breaux, Tatiana Hazel, Sir & Madame, TRAP House Chicago, Abigail Glaum-Lathbury. Prime Time tickets include a timed entry to the exhibition Virgil Abloh: “Figures of Speech.”
COST :: Tickets start at $40 | Click here for more info
WHAT :: Roosevelt Collection Rooftop Vintage Market
WHERE :: Shops at Roosevelt Collection | 150 West Roosevelt Road
WHEN :: Saturday, June 29 10 a.m. – 4 p.m.
WHY :: Guests are welcomed to The Rooftop at Roosevelt Collection to peruse and shop handmade goods and handpicked vintage items from small businesses located throughout the Chicagoland area.
COST :: Free to attend
WHAT :: I|O Godfrey Rooftop Garden Party

WHERE :: I|O Godfrey at The Godfrey Hotel Chicago | 127 W. Huron Street
WHEN :: Saturday, June 29, 12-6 p.m
WHY :: This kick-off to the summer season encourages guests to wear their summer best while enjoying sweeping views of the city, lawn games on the rooftop’s outdoor portico, and grill stations serving summertime classics. Each Garden Party ticket includes one Botanical Spritz cocktail which guests can customize from an assortment of flavors. Guests can also choose from a variety of seasonal dishes and drinks, such as a boozy Blueberry Mania Push-Pop.
COST :: Tickets start at $25 per person | Click here for more info
WHAT :: yacht & bothered: Fools Gold Records Boat Party

WHERE :: Anita Dee II @ DuSable Harbor | 200 N. Breakwater Access
WHEN:: Saturday, June 29, 12 PM Board, 1 PM Disembark
WHY :: Join A-TRAK & Friends (Fool’s Gold) take over boat party with Nick Catchdubs, Boi Jeanius and Ron Carroll.
COST :: Tickets start at $34.50 per person | Click here for more info

WHAT :: Pride In The Park Chicago
WHERE ::Butler Field @ Grant Park | 377 E Monroe Street
WHEN :: Saturday June 29
WHY :: ‘Twas the night before the Chicago Pride Parade and alll gathered at Grant Park to watch acts such as Iggy Azalea, Steve Aoki, Tamar Braxton, Taylor Dayne, Todrick Hall and many more as Chicago celebrates the 50th pride parade.
COST :: GA tickets start at $55 | Click here for more info
WHAT :: Chef Julius’ BBQ Pop-Up: A Return To The Smokehouse
WHERE :: Taste 222 Chi | 222 N. Canal Street
WHEN :: Saturday June 29 from 4-8pm
WHY :: Chef Julius is creating a summer BBQ experience. This year Chef is bringing something new… WHOLE HOG to Chicago, just for this event! ALL of the side dishes will be vegetarian or vegan.
COST :: Tickets start at $80. | Click here for more info.
SUNDAY JUNE 30
WHAT :: Chicago 50th Pride Parade

WHERE :: Montrose Avenue and Broadway in the Uptown neighborhood
WHEN :: Sunday, June 30 Noon
WHY :: Chicago’s month of Pride celebration culminates with the 50th annual Chicago Pride Parade marching through the city’s Boystown neighborhood. The parade’s theme this year is “Stonewall 50: “MILLIONS of MOMENTS of PRIDE.”2019 marks the 50th Anniversary of the uprising, outside New York’s landmark Stonewall Inn, which began the Gay Rights Movement. Several bars and restaurants in the area will be offering specials and more.
COST :: Free to attend | Click here for more info
WHAT :: Do the Right Thing Block Party
WHERE :: Stony Island Arts Bank | 6760 S Stony Island Avenue
WHEN :: Sunday June 30 12:00pm – 10:00pm
WHY :: Head down to Stony Island Arts Bank for the celebration of the 30th anniversary of Spike Lee’s most prolific joint, Do The Right Thing (1989) Hosted by Duane Powell & Friends. Join us for an all-day block party celebration honoring the film that still has society asking, “Did Mookie do the right.
COST :: Event is FREE | Click here for more info
WHAT :: Jennifer Lopez It’s My Party Tour at United Center
WHERE :: United Center | 1901 W. Madison Street
WHEN :: Saturday June 29 & Sunday June 30 8:00 PM
WHY :: Jennifer Lopez aka Jenny from the Block aka Jlo’s highly anticipated It’s My Party Tour, her first ever US headlining tour, will make its Chicago stop June 29 and June 30. World of Dance finalists Swing Latino and Briar Nolet, and season one winners The Lab will join her as special guests to open the tour. It’s My Party Tour will feature a nonstop party mix of Jennifer’s new and classic anthems, showstopping choreography and dancers, dazzling wardrobe, jawdropping technology and set design, and all of the glamour and wow-factor fans have come to expect of Jenny from the Block.
COST :: Tickets start at $39.95 | Click here for more info
- Honorable mention: The Lyrical Lemonade Summer Smash 2019 Fest at Douglas Park
Sat, Jun 29 – Sun, Jun 30 Click here for more info. - Chitown Hot Sauce Expo @ Seatgeek Stadium in Bridgeview July 29 & 30 Click here for more info.
Whatever you do, if you will be outdoors for a long duration of time, remember sunscreen and hydration (water not just alcohol). Have a great weekend!
*featured image credit: KAMIL KRZACZYNSKI/AFP/Getty Images via WGN
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