Al fresco dining, lakefront outings, and street fairs galore all point to one truth: Summer in Chicago simply can’t be beat. Unfortunately, the season is over in the blink of an eye, making way for the city’s action-packed autumn calendar before we’ve even had time to dust off our new patio digs or master this year’s music fest looks.
To help ensure you take full advantage of this town’s most terrific time of year, we’ve rounded up a few of its biggest summer musts, from a movie in the park to the food festival of a lifetime.
Summer evenings don’t get any better than those spent at Ravinia, the oldest outdoor music festival in North America. Established in 1904, the Highland Park destination has hosted some of the music world’s biggest talents from Louis Armstrong and Ella Fitzgerald to George Gershwin and Janis Joplin. A typical three-month season sees more than 600,000 listeners, who lay down blankets; snack on wine and cheese; and take in the dreamy, tree-canopied fest grounds (à la A Midsummer Night’s Dream). This year, be sure to catch the inimitable Steve Martin and Martin Short (August 12), John Hiatt and the Goners (August 30), and the Gipsy Kings (September 14).
What’s better than a stash of your favorite candy, good company, and an all-time favorite film? Seeing said film outside, of course. Thankfully, the Chicago Park District has moviegoers covered with outdoor, citywide programming including an impressive lineup of must-see shows all summer long. Don’t miss Wonder Woman at Augusta Park (August 7), Back to the Future at Webster Park (August 13), or Space Jam at Davis Square Park (September 12).
Located directly next to Wrigley Field, this open-air gathering hub is teeming with attractions for Chicagoans and visitors alike. Concerts, farmers’ markets, and free fitness classes with Chicago Athletic Clubs are all offered here, along with an array of special events throughout the season. Explore local food finds with the Green City Market on select Thursdays through September 20, and expect free, outdoor musical performances featuring classical, jazz, and folk genres to be showcased all summer long. Pre-shows are a perk, too — on September 7, ticket holders to the Billy Joel concert at Wrigley Field can come early for eats, drinks, and live tunes from Atlanta-based singer-songwriter Alex Guthrie.
These 385-acre gardens are particularly gorgeous in summer, thanks to a growing number of in-bloom sights (from geraniums and roses to hydrangeas and waterlilies) — and there is the wide array of onsite classes, activities, and special events hosted there, too. Bring a friend for one of the site’s regularly occurring yoga practices on Tuesdays and Thursdays, or try your hand at any of the scheduled cooking classes (Hands-on Cooking: Regional American happens on August 23). On August 25 and 26, join them for their Heirloom Fest, where visitors can explore displays and demos to learn about how to grow and use a variety of heirloom vegetables.
Festivals may happen year-round in a city like Chicago, but they’re best during the summer months, when the celebrations head outside. August sees some of the biggest ones of the season, including Lollapalooza (August 2–5), Retro on Roscoe (August 10–12), and the Chicago Air and Water Show (August 18–19). In September, the fun continues with Riot Fest (September 14–16) and Sam Adams Lakeview Taco Fest (September 15–16). Food lovers, mark your calendars well in advance: Chicago Gourmet (September 26–30) is the ultimate gastronomic jamboree, offering bites and sips from some of the country’s most lauded chefs and winemakers.