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4 Can’t-Miss Cultural Moments in Chicago This June
Plus, where to grab a bite while you’re there.
Summer is what Chicagoans spend all winter earning. With the calendar turning to June, it’s time to hit a street fair, dine al fresco, and catch live entertainment in the park — maybe all in one weekend. Here are four cultural events happening this month you won’t want to miss.
Jam Out At The Largest Free Blues Festival
One of the city’s most beloved summer traditions, the Chicago Blues Festival sees top blues musicians taking over Millennium Park for three days of performances June 5-7. The festival, which honors Chicago’s rich blues heritage, runs noon to 9 p.m. daily across multiple stages and features headliner talent like Taj Mahal as well as up-and-coming names. This year’s fest also brings a 55th anniversary tribute to Alligator Records and a salute to 75 years of Billy Branch.
When you need a break from the music, use DoorDash Reservations to book a table for dinner at Rose Mary, a Croatian restaurant in the Fulton Market district that’s named for chef-owner (and Top Chef winner) Joe Flamm’s grandmothers. The expansive dining room features whitewashed brick walls, oak dining furniture, and blue-and-white tile work that is meant to evoke the feeling of a family-run tavern, making the perfect setting for enjoying the coastal-inspired menu. Plates are shareable, so you can choose one from each category; standouts include the zucchini fritters, grilled clams, tortellini djuvec, and pork ribs pampanella.
Watch A Movie Under The Stars
While the Millenium Park Summer Film Series doesn’t kick off until the end of the month, you can catch movies at other parks around the city starting June 9 when Movies in the Parks returns for its 26th season. This month’s picks include retro fan-favorites like Back to the Future, Ferris Bueller’s Day Off, and Remember the Titans — all screening for free.
Start your evening with dinner at Elina’s, which serves comfort-food Italian classics like rigatoni alla vodka, meatballs, and shrimp scampi in an intimate, elevated setting. Be sure to reserve a table in advance via DoorDash reservations so that you can make it to the park before the movie starts.
Celebrate Summer At A Swedish Street Festival
One of the best things about Chicago in the summertime is there’s a neighborhood street fair happening basically every weekend. On June 12-14, it’s Andersonville’s , marking its 60th year of celebrating Swedish traditions. More than 50 music acts will perform across four stages throughout the weekend, and food vendors and artisans selling their wares provide a break from the entertainment. Don’t miss the annual maypole raising happening Saturday at 11 a.m. on the Swedish Stage.
While it’s not Swedish food, Andros Taverna in Logan Square makes a good brunch stop before hitting the fest since it’s now open weekends at 9 a.m. Reserve a table in the sun-drenched dining room via DoorDash reservations and enjoy Greek-style breakfast dishes like Tsoureki French toast, pita stuffed with cheesy egg, and Koulouri (Greek bagels). Don’t forget to order an almond freddo, made with frothed and strained espresso poured over cold almond milk, a Greek specialty.
Show Your Pride At Pride Fest
The weekend before the Pride Parade, the celebrations officially kick off at the Chicago Pride Fest happening June 20-21 in the historic LGBTQ+ Northalstead district. The vibrant LGBTQ+ culture and community will be on full display with live music across three stages, drag shows, dance exhibitions, a performance by the Chicago Gay Men’s Chorus, and even a Proud Pet Parade. A $20 suggested donation helps pay performers and festival workers, and new this year, you’ll find VIP areas with AC tents, private bars, and lounge seating.
Before hitting the festival, reserve a table via DoorDash Reservations for brunch at Mano a Mano, a neighborhood Italian spot in Logan Square. Grab a booth or high-top inside the moody dining room, then choose from a selection of Italian pastries, panino egg sandwiches, antipasti, eggplant or chicken Parm, and, of course, pasta for a proper carb-loading. Or, if you prefer to head there post-fest, stop in for their Spaghetti Sundays, where you can enjoy antipasti, a salad, choice of spaghetti, and gelato for just $45 per person.
