June 1: Wu-Tang Clan—In support of the 25th anniversary of their breakthrough album, “Enter the 36 Chambers,” Wu-Tang Clan come back to Chicago for a rowdy celebration of one of the greatest hip-hop albums of all time.
June 2: Do Division Street Fest—Spanning several blocks of the trendy Wicker Park neighborhood, Do Division features a massive sidewalk sale, food from local restaurants, a fashion show featuring Chicago designers and even a kid-friendly petting zoo. This year’s musical lineup features performances from local metal trio Russian Circles, throwback rap duo The Cool Kids and much more. Also May 31 and June 1.
June 3: Rembrandt Portraits—A Dutch master craftsman widely known for his subtly opulent Baroque paintings during the 1600s, Rembrandt has become one of the world’s most celebrated artists. The Art Institute of Chicago currently has an exhibit showcasing some of his most famous portraits such as “Old Man with a Gold Chain.” Afterwards, make sure to stop by the museum’s acclaimed Modern Wing for a guided tour of modern artworks by a lecturer. Runs through June 9.
June 4: Anderson .Paak—Finding artistic inspiration at the intersections of R&B and hip-hop, Anderson .Paak is one of the most eclectic rappers currently in the game. His new album “Ventura” feels like an aural summer breeze with smooth production that seems destined to soundtrack cookouts throughout the season. Tonight, he returns to Chicago for a stacked show at Huntington Bank Pavilion at Northerly Island with funk virtuoso Thundercat and local rap poet Noname.
June 5: Ariana Grande—Armed with a full band, Ariana Grande is bringing her massive Sweetener World Tour to the United Center for a night of anthemic feminist pop jams such as “God is a Woman.” Now is your chance to see her in a somewhat intimate club setting before she headlines Lollapalooza later this summer.
June 6: Summer Sippers—Head to Eataly and experience the seaside coasts of Italy with their new summertime pop-up, Bar SABBIA. Meaning “sand” in Italian, the bar features fresh oysters, thrilling calamari pastas and regional Italian wines. To celebrate the summer season, Bar SABBIA is hosting a sophisticated party with refreshing small plates of seafood and an open bar with frozen rosé and spritz cocktails.
June 7: Spring Awakening—The Chicago area’s premiere EDM festival takes over a new home at Poplar Creek in Hoffman Estates, right outside the Sears Centre. Join Zedd, DJ Snake, Dillon Francis and many more for a weekend with some of the most exciting names in dance music. Also June 8-9.
June 8: Printers Row Lit Fest—Just south of the Loop is the Printer’s Row district, which was at one point the publishing hub of Chicago. These days most of the publishing houses have moved on, but the area’s heritage of literature lives on with Printers Row Lit Fest, the largest free outdoor literary festival in the Midwest. Lose yourself in stacks of wondrous and rare books from over 100 booksellers. Take a seat and listen to one of the many authors showcased at the festival, such as University of Chicago professor and Marvel Comics writer Eve Ewing, and Valerie Jarrett, the former senior advisor to President Barack Obama. Also June 9.
June 9: Bears 100 Celebration—The Chicago Bears are turning 100 and are celebrating with a massive party this weekend at the Donald E. Stephens Center in Rosemont. Spend the weekend hanging out with the current team roster as well as Bears legends such as Mike Ditka and Brian Urlacher who will participate in photo sessions, autograph opportunities, activities for the kids and much more. Also June 7-8.
June 10: The Dog’s Day—A collaboration between no-kill dog rescue group One Tail at a Time and Emporium Arcade Bar, The Dog’s Day is a dog friendly pop-up bar in Logan Square that aims to end pet homelessness one ice cold beer at a time. Runs through June 30.
June 11: Little Simz—Little Simz is an artist who is part of London’s thriving music scene that has won over crowds throughout the U.K. with her series of mixtapes that seamlessly blend hip-hop and R&B. Based on the strength of her breakthrough single, “Selfish,” she was invited to perform at Coachella and has since embarked on a North American tour. Tonight, she touches down at Lincoln Hall for a night of smooth London soul.
June 12: “Clueless”—When the Cubs aren’t playing at home this summer, you can catch movies at Gallagher Way, the small yet stylish park right outside of Wrigley Field that is anchored by trendy restaurants such as the award winning taqueria, Big Star. Tonight is a free screening of the ‘90s teen comedy classic, “Clueless.”
June 13: After Hours Buzz—Learn all about bees and beyond at the Chicago Botanic Garden in suburban Glencoe when they host a sophisticated adults only after party. In addition to lectures, enjoy a cocktail while exploring an enthralling garden full of wonderful and exotic plants.
June 14: Buddy Guy—The undisputed king of Chicago Blues has seen it all and shared the stage with everyone from Howlin’ Wolf to The Rolling Stones. Tonight, he performs at Ravinia in suburban Highland Park with the North Mississippi Allstars and Shemekia Copeland.
June 15: Taco & Tequila Fest Chicago—Tacos and tequila make a winning combination at thyis festival. Wander around the park while trying some of the best tacos in the city paired with tastings of rare tequilas.
June 16: Father’s Day Ribfest—This Father’s Day, take Dad to Frontier in the Noble Square district for an afternoon of all-you-can-eat ribs and sides such as cornbread, baked beans and mac and cheese. When you get thirsty, wash it all down with craft beer specials from Spiteful Brewing.
June 17: South Side Salsa—Head to Hyde Park and let the rhythm take control. Tonight, trendy nightclub The Promontory hosts a free dance lesson that’ll teach you how to do the salsa. Afterwards, put those caliente moves to work as DJs play the very best in Latin dance all night long.
June 18: Goat Visits—Spend the day with goats at the Garfield Park Conservatory. In addition to being the perfect backdrop for your next selfie, the goats help maintain the plant population by grazing the fields.
June 19: Cubs Vs. White Sox—It’s time for the Crosstown Classic at Wrigley Field as the Cubs take on the White Sox as the two Chicago teams continue their storied rivalry. Also June 18.
June 20: Digable Planets // Kweku Collins—You don’t need to live in the city to participate in Chicago’s thriving music community. Head just over the border to Evanston and check out SPACE. Inside, you’ll find speakeasy aesthetics with modern sophistication. Tonight, they’re hosting performances by the Grammy award winning ‘90s jazz rap trio Digable Planets and emerging local psychedelic rapper Kweku Collins.
June 21: LakeShake Festival—Returning to Chicago for another year of Nashville hot country music, LakeShake takes over Huntington Bank Pavilion at Northerly Island for a weekend with Keith Urban and Luke Bryan. But we’re most excited for the (almost) all women lineup on Friday anchored by Miranda Lambert and pop country singer Maren Morris. Also June 22-23.
June 22: Chicago Pride Fest—Chicago celebrates Pride Month with a wide variety of activities, including the 19th annual Chicago Pride Fest, two days of celebration the weekend before the Chicago Pride Parade. The theme during this year’s festivities honors the 50th anniversary of the Stonewall Riots and the start of the LGBTQ rights movement. During Pride Fest enjoy an array of performances, from drag shows to DJs as well as this year’s headliner, Leann Rimes. Also June 23.
June 23: Ruido Fest—Meaning “noise” in Spanish, Ruido Fest is Chicago’s only music festival that focuses exclusively on the best in Latinx punk, metal, electronica, R&B and hip-hop. In previous years, they’ve invited acts such as Colombian indie sensation Kali Uchis and Mexican alternative rock heavyweights, Cafe Tacuba. This is the fest’s 5th anniversary and they’re celebrating in a big way with a new location at Union Park with acts like Ecuadorian folk crooner Helado Negro and Chilean reggaeton rapper Tomasa del Real and more scheduled to perform throughout the weekend. Also June 21-22.
June 24: “Black Panther”—A sure sign of summer in Chicago are the free movie screenings throughout the city. Tonight, Navy Pier is hosting a free screening of “Black Panther” on the lakefront. Nominated for the Academy Award for Best Picture, the movie features incredible costume designs, a fantastic soundtrack and amazing performances from world-class actors such as Chadwick Boseman, Lupita Nyong'o and Michael B Jordan.
June 25: Rolling Stones—Earlier this year, The Rolling Stones were set to go on tour when they were forced to postpone due to a medical complication that required Mick Jagger to undergo surgery. Now that Jagger has recovered, the band is hitting the road and taking over Soldier Field as part of their massive worldwide No Filter Tour with essential rock classics such as “Gimme Shelter” and “Sympathy For the Devil.”
June 26: Summerfest—Much like Lollapalooza, hopping on the Amtrak and making a trip to Summerfest is a rite of passage of summertime in Chicago. The yearly festival takes place a little over an hour away in Milwaukee on the shores of Lake Michigan. This year’s lineup is quite impressive with Lil Wayne, Billie Eilish, The Killers, Jennifer Lopez and more scheduled to headline throughout its run. Runs through July 7.
June 27: Try Guys—Formerly stars of Buzzfeed’s series of viral videos, The Try Guys launched their own YouTube channel a few months ago. Tonight, Keith, Ned, Zach and Eugene take over the Chicago Theatre as part of their nationwide Legends of the Internet tour for a provocative night of friendship and comedic spectacle.
June 28: “Boyz n the Hood”—As part of a retrospective series examining the works of director John Singleton, Music Box is hosting a midnight screening of quintessential ‘90s drama, the Oscar nominated "Boyz n the Hood.” Featuring powerful performances from Laurence Fishburne, Cuba Gooding, Jr. and Ice Cube in his film debut, this tale of three childhood friends coming of age while trying to escape the cycle of gang violence on the streets of L.A. is just as potent almost 30 years later. Also June 25 and 29.
June 29: Randolph Street Market—Featuring one-of-a-kind vintage jewelry, the trendy Randolph Street Market returns to offer up all the vinyl records, stylish decor and bohemian artwork that your dream home can handle. Also June 30.
June 30: Pride Parade—Head to Boystown this afternoon at the annual Pride Parade. Now drawing crowds over a million people, the parade features fantastical floats and dancers that aim to celebrate LGBTQ equality in Chicago and beyond.