The Second City

Innumerable comedians, actors, and directors have honed their craft as members of this legendary comedy troupe. Show your children where some stars such as Dan Castellaneta of The Simpsons, Tina Fey of Saturday Night Live, and Steve Carell of The Office got their feet wet on stage, and cement your status as a pop-culture guru.

Contact number: (312) 337-3992

Location: 1616 North Wells Street, Chicago, IL 60614

Learn more here.

Steppenwolf Theater

Gary Sinise, Terry Kinney, and Jeff Perry founded this Tony Award-winning ensemble in a church basement in 1974. Today’s incarnation of Steppenwolf is one of the country’s longest-standing and highest-quality theater ensembles, remaining true to the founders’ original vision of dynamic and electrifying theater. The company’s Family Performance Series is the perfect opportunity for you to introduce your children to or further their passion for stage-acting. The series includes four plays at a reduced and very reasonable ticket price, and each performance is preceded by an interactive reception with Steppenwolf artists.

Contact number: (312) 335-1650

Location: 1650 North Halsted Street, Chicago, IL 60614

Learn more here.

Short Shakespeare!

Good luck sharing with your children the metaphorical implications of Henry IV. That’s where Chicago Shakespeare Theater comes to save the day with its Short Shakespeare! series. The company abridges the Bard’s plays to 75-minutes, and also adapts the plays for all ages, making it an interesting way to introduce your children to an integral part of literary history. You’re all sure to laugh your way through Katherine’s antics in The Taming of the Shrew.

Contact number: (312) 595-5600

Location: 800 East Grand Avenue, Chicago, IL 60601

Learn more here.

Old Town School of Folk Music

Chicago is known for is its robust and long-lasting folk-music scene, and there’s no better place to get your children acquainted with the genre than at the Old Town School of Folk Music. Kids’ events are held year-round, featuring some of the city’s finest strummers and crooners, all offering fun, sing-along type jams, palatable to children of all ages and the parents who love them. Free and frequent “Wiggleworms” events provide fun activities for toddler-children with the same lively musical backdrop; classes and workshops are also offered through the school if your children are struck with post-concert inspiration.

Contact number: (773) 728-6000

Location: 4544 North Lincoln Avenue, Chicago, IL 60625

Learn more here.

Noble Horse Theater

Young horse enthusiasts will be awestruck by these breathtaking animals’ tricks and performances. Trained and brought over from different parts of the globe, beautiful stallions, Spanish-Andalusian, and Egyptian-Arabian horses delight and entertain year-round and in seasonal shows like Legend of Sleepy Hollow and The Nutcracker. It all takes place in an elegantly appointed theater that was built in 1871 and is now Chicago’s last performing-horse theater. If the children are thoroughly amazed after the show, you can book a carriage ride through the city, pulled by an equally magnificent equus.

Contact number: (312) 266-7878

Location:1410 North Orleans Street, Chicago, IL 60610

Learn more here.

Chicago Kids Company

This theater company produces colorful and wildly entertaining live performances for children, ages 2 to 12. Each play is adapted from a classic fairy tale and updated to match your children’s frame of pop-culture reference, making a show here the perfect primer for your budding theater buffs. Performances are held all year long at different venues in the Chicago area.

Contact number: (773) 205-9600

Location: 4104 North Nashville Avenue, Chicago, IL 60634

Learn more here.

Chicago Jazz Festival

This Chicago institution brings on such legendary headliners as Sonny Rollins and Ornette Coleman, who take the stage in late August. The Chicago Jazz Festival is one of the most extensive free jazz festivals in the world and features the work of pioneers like Duke Ellington, as well as the contemporary piano stylings of giants like Herbie Hancock. The four-day festival also incorporates an art fair and Chicago’s world famous restaurants to harmonize with all your senses. And for your children, making its debut is an all new kids activity area to occupy them mind, body, and soul.

Contact number: (312) 774-3315

Location:300 South Columbus Drive, Chicago, IL 60604

Learn more here.

Chicago Gospel Festival

Immerse your children in the rich history of Chicago gospel music at the city’s outdoor festival. If gospel speaks to your soul, the Chicago Gospel Music Festival will lift your spirits with the delivery of artists like The Clark Sisters and Darius Brooks. A musical tradition dating from the early 1920s, gospel’s rich heritage is as infectious as it is inspirational; at the show, you and your children will find yourselves rising to your feet in celebration. The event is now in its 24th year and features more than 50 performers during its three days, with three stages of music and activities for all ages. Children will love the Gospel Youth Tent — a stage dedicated to the youth choir, gospel rap, and drum line.

Contact number: (312) 744-3315

Location:210 East Randolph Street, Chicago, IL 60601

Learn more here.

Chicago Country Music Festival

This festival has drawn headliners to Chicago’s stage, including Emmylou Harris, Dwight Yoakam, Faith Hill, Keith Urban, George Jones, Waylon Jennings, Wynonna, Randy Travis, and Loretta Lynn. The three performance stages and dance tent are sure to feature performances that will delight. With activities, including square dancing and karaoke, the children will be hootin’ and hollerin’ with the best of ’em. If that isn’t enough, the festival also has a Kid Corral with special programs like kids’ crafts, storytelling, and a mural that your children can color. Wiggleworm instructors from The Old Town School of Folk Music will be on hand to lead interactive sing-alongs, too.

Contact number: (312) 744-3315

Location:425 East Mcfetridge Drive, Chicago, IL 60605

Learn more here.

Chicago Blues Festival

If you’re looking for the home of the blues, look no further than Sweet Home Chicago. The Chicago Blues Festival is the largest of the city’s outdoor music events, drawing nearly 750,000 blues’ fans during its four days to enjoy the event’s six stages of performances. Now in its 25th year, the mid-June festival attracts the biggest names in blues, from the Queen (Koko Taylor) to the legendary (B.B.) King himself. Whether you’re a resident or just a passer-through, introducing yourself and the children to the culture of Chicago means listening to blues, and this free concert festival is just the ticket.

Contact number: (312) 744-3315

Location: 300 South Columbus Drive, Chicago, IL 60601

Learn more here.