The granddaddy of America’s music festivals, Chicago’s Lollapalooza (August 3–6 this year) packs 100,000 fans a day into skyscraper-surrounded Grant Park, where crowds rock out to more than 140 bands over four days, including headliners like Radiohead and Paul McCartney. The festival attracts music fans of all ages, especially younger crowds. If you love music, it’s a party you don’t want to miss.
The Grant Park crowds are mellower at the Chicago Blues Festival, better known as Blues Fest (June 9–11). As you’d expect in a city famous for its blues, the lineup features some of the genre’s best acts. Admission is free, and the pavilion fills with fans who nod their heads to the slow tunes and dance to high-energy blues funk. Don’t be surprised if legends such as Buddy Guy (who has a blues bar down the street) make a guest appearance.
Get more thrills dancing in Grant Park during Chicago SummerDance, a free outdoor summer dance party on Fridays, Saturdays and Sundays (June 23–September 10). Each weekend night features a different dance style, like swing, salsa, waltz or Bollywood. After a group dance lesson, a live band plays as you try out your moves on the basketball-court-sized dance floor.
For live music in a low-key setting, pack your finest picnic gear and head to tree-covered Ravinia Festival on the North Shore in Highland Park. Set up lawn chairs and uncork wine while listening to classical music or popular acts like James Taylor. Fireworks cap off musical performances during the free Rockin’ in the Park concert series in Rosemont (Thursdays between Memorial Day and Labor Day). Local food tents dot the open green in MB Financial Park, so be sure to come hungry (and don’t forget lawn chairs).
• Check the schedule in advance to see what type of dance is being taught on which night. That way you don’t show up to learn Bollywood dancing on a night they’re featuring salsa.
• Bring the kids! SummerDance is a family friendly event.
• Don’t want to drag lawn chairs and coolers? Preorder a picnic box dinner and rent chairs there. Or, park in the Highland Park Metra lot, eat dinner in downtown Highland Park, and take a free shuttle bus to Ravinia.
• It’s hard see the stage from the lawn seats, so get there early to grab a spot with a clear view of the video screens showing the stage. It’s the next best thing.
"Whoa, cool!” is a phrase you’ll hear often while watching military jets whiz past, spin and perform other incredible tricks at the Chicago Air and Water Show (August 19–20). Nearly two million spectators line the downtown lakefront for the two-day show. Celebrate a different type of soaring star at the annual Superman Celebration in Metropolis (June 8–11). The Man of Steel’s “hometown” honors its native son with panel discussions, celebrity guests and other Superman-themed activities, including costume contests and carnival rides and games.
Dozens of hot-air balloons fill the skies during the Great Galena Balloon Race (June 16–18) before they land at Eagle Ridge Resort and Spa. You won’t reach the sky, but you’ll get up to 100 feet in the air during a tethered balloon ride at Eyes to the Skies in the western suburb of Lisle (June 30–July 2). This fund-raiser for local charities also features nightly balloon glows and fireworks, carnival rides and live music.
Chicago’s Printers Row Lit Fest (June 10–11) stacks five city blocks with book-filled booths from publishers big and small. Peruse their displays for new, used, antique and kids’ books. Discover a breakout writer, or check out a celebrity author. Honor the world’s most famous playwright during Bloomington’s Illinois Shakespeare Festival (June 30– August 12). Picnic on the grounds of the Ewing Cultural Center before watching traditional and creative stage versions of the Bard’s works, such as Cymbeline or A Midsummer Night’s Dream. Tickets to these high-quality shows start at just $12.
A more tangible art form makes the Geneva Arts Fair (July 22–23) a nationally renowned festival (40 miles west of Chicago). More than 150 juried artists exhibit and sell their work in this town along the Fox River. You’ll be tempted to take home your own painting, sculpture or piece of handmade jewelry from the lineup of high-quality, can’t-find-it-in-a-store work. That’s also the case at the Midsummer Arts Faire in Quincy (June 3–4), the Springfield Old Capitol Art Fair (May 19–21) and the Art on the Square in Belleville (May 19–21).
Grab some extra napkins, because you’ll have sauce-covered fingers from eating the meaty ribs at Ribfest in Naperville. Away from the grills, well-known music acts perform and families line up for carnival rides and games, with fireworks capping off the night. More tasty ’cue—plus a smorgasbord of live entertainment—awaits in Chicago at the Windy City Smokeout (July 14–16).
Menus get more diverse at Taste of Chicago (July 5–9), with more than 60 restaurants and food trucks along downtown’s lakefront. While you can try Chicago’s famous deep-dish pizza, save room for unique ethnic dishes, like African sautéed goat, a Puerto Rican jibarito sandwich or Polish pierogies. Taste buds get a kick at the International Horseradish Festival in Collinsville (June 3–4). Try horseradish pot roast, spiral potatoes with horseradish seasoning and a horseradish-infused Bloody Mary before shopping for homemade crafts and then watching—or competing in—the annual Root Games.
Taste of Champaign-Urbana (August 18–19) doubles as a fundraiser for local youth programs in Champaign’s park district. During the day, it’s a family-friendly fest with inflatables, artist demonstrations and games. After the sun goes down, it transforms into more of an adult party, with a hopping beer tent and headlining music acts.
Follow the scent of homemade peach cobbler to southern Illinois’ Cobden Peach Festival, which has lured visitors to this town of 1,100 since 1938. Besides the out-of-this-world cobbler, fest-goers snack on freshly sliced peaches from local farmers while taking in the family-friendly parade, carnival rides and games.
You’ll find plenty of good local eats along a 90-mile stretch of the former Mother Road during the Illinois Route 66 Red Carpet Corridor Festival (May 6–7), when twelve communities celebrate the community spirit of the road with special events. Get your comfort-food fix at stops such as the Old Log Cabin, serving hearty breakfasts and meaty burgers and melts in Pontiac.
Chicago foodie and Instagrammer Samantha Roby visits Galena, and shares her exp...