Fun Fests

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). 

Lollapalooza

• Tickets sell out quickly, so be ready to make your purchase the exact minute they go on sale in the spring, or you’ll have to pay more through a ticket broker.
• Don’t miss Chow Town, a food festival within the festival, where some of the city’s best restaurants serve fest-friendly food like gourmet lobster corn dogs.

Chicago Blues Festival

• During the day, tour Blues Heaven Foundation, a small blues museum on Michigan Avenue at the site of the old Chess Studios, where legends such as Muddy Waters and Bo Diddley recorded songs.
• Getting in and out of Grant Park can take forever on crowded nights. Book a downtown hotel room in advance so that you’re close to the action.

"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).

Printers Row Lit Fest

• Buy a weekend-long Fest Pass for access to express book-signing lines and freebies like an e-book, poster and tote bag.
• Download the Lit Fest app, which allows you to build your schedule, get discounted e-books, see up-to-date schedules and more.

Illinois Shakespeare Festival

• Going with kids? Check out their 45-minute family shows.
• For $10 per person, one of the actors will take you on a pre-show backstage tour.

Geneva Arts Fair

• Although Geneva is famous for this arts fair, it’s also known for its chocolate. Grab a few pieces at any of the dozen specialty chocolate shops in town.

Midsummer Arts Faire

• If the kids are bored, get a day pass to The Salvation Army Ray and Joan Kroc facility, an impressive community center, one block north of the festival site.
• The nearby Park Bench restaurant is a comfy place to go for coffee, a light breakfast, or soup, salad and a sandwich for lunch.

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.

Ribfest

• From noon to 3 p.m., you can score a $10 wristband to enjoy unlimited carnival rides.
• Let the kids vote for their fave ribs and help decide who wins the Kids’ Choice Award.
• During the fireworks show, tune in to 104.3 FM, which simulcasts music to accompany the spectacle.

Taste Of Chicago

• Order the smaller and less expensive “taste” menu items, so that you’ll have room in your stomach and budget to sample more foods.
• The best time to visit is during the weekday lunch hour, when the crowds are significantly smaller.

International Horseradish Festival

• Take home a jar of freshly grated Illinois-grown horseradish, said to be tastier than anything you can buy in a grocery store.
• See if you can win Root Toss, Root Golf or any of the other quirky games featuring horseradish roots.

Taste Of Champaign-Urbana

• Burn off some calories with the Pie Run, a 3.14-mile dinnertime run with homemade pie samples (and water) along the route. If you choose, you can have a “flying pie” thrown at your face for a photo op when you cross the finish line!
• Park for free in the area on Saturdays—the parking meters will not be enforced.

Cobden Peach Festival

• Watch to see which lucky winner will take home the Peach Queen crown.
• For a taste of small-town Americana, go to the Saturday night Peach Festival parade—the highlight of the weekend.