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14 best things to do with kids in Chicago in May

Written by
Laura Rote
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Our May events calendar has no shortage of family-friendly events, and we don't just mean trips to the best playgrounds and toy stores. To the contrary, the month of May has some unexpected opportunities in store for kids, whether they want to climb in a firetruck, fly a kite or hop in a canoe for the first time. Here are just some of the best things to do with kids in and around Chicago in May. 

1. Touch a Truck Family Festival. It seems like every little kid is obsessed with big vehicles, whether it's a dump truck or an ambulance. This family festival gives them a chance to climb in, honk the horn, have their photos taken and more. Proceeds benefit programming at Kohl Children's Museum. (Ravinia North Parking Lot, 418 Sheridan Rd, May 1, 11am. $45 for a family of up to six people) 

2. Jabari Dreams of Freedom. This children's play tackles heavy subject matter in a creative way, as its lead character Jabari uses art to travel back in time and talk with famous people as children. (Chicago Children's Theatre, 1144 W Madison St, May 1, 11am–noon. $20)

3. Tales of Yore. Take the kids to see how music, storytelling and puppetry combine in this coming-of-age tale set in ancient China (Fine Arts Building, 1335 S Michigan Ave, May 2, 7:30pm. $10–$40) 

4. Penelope Pennyworth Girl Detective: Case of the Boogeyman. Penelope saves the day in this adorable children's theater production about a young crime-solver at the new Edge Theater in Edgewater. (Edge Theater, 5451 N Broadway, through May 8. $10 and up)  

5. Cinco de Mayo Pinata Party. This Cinco de Mayo event may be after May 5, but it's no less festive. The kids can spend the afternoon making colorful pinatas, then head out to see their favorite animals at the zoo. (Lincoln Park Zoo, 2001 N Clark Street, May 7 & 8, 1:30–3:30pm. $5 per person, $4 for zoo members)

6. Kids and Kites Festival. Both the young and the young at heart will get a kick out of running through the park at this colorful, high-flying event. You can make your own kite here while supplies last, buy a kite on-site or simply sit back and watch the professionals do it. (Cricket Hill, May 7, 10am–4pm. Free)

7. The Chicago Youth Comedy Festival. Your teen have a funny bone? Sign her up for a workshop in physical comedy. (Stage 773, 1225 W Belmont Ave, May 7. $125) 

8. Bird ID Canoe Cruise. What? Bird ID Canoe Cruise! Climb in a boat and identify some rare and beautiful birds in the early morning as you float through the waters at Skokie Lagoons. Reserve your spot early, as boats are limited. (Skokie Lagoons, Tower Road Boat Launch, Winnetka, IL, May 10, 6:30am. Free)

9. Cinderella. While many little girls dream of trying on that famous glass slipper, just as many dream of actually being a ballerina. Take the family to experience this magical performance from the Joffrey Ballet, and you won't soon forget it. (Auditorium Theatre, 50 E Congress Pkwy, through May 22. $35 and up) 

10. Nature Block Party: A Celebration of Biodiversity. Your kids can learn about restoration while making crafts or going on hikes and bike rides as part of this block party event. (Eggers Grove, 11201 S Ave B, May 14, 11am. Free) 

11. Stem Step 5K. Sign the kids up to go for a run. Little ones can opt for the kids' dash, while your track stars can join you in the 5K. Proceeds benefit local schools' STEM and athletics programming. (Humboldt Park, 1400 N Sacramento Ave, May 14, races begin at 8:30am. $10 and up)

12. Homewood Rail Fest. Venture out to neighboring Homewood with your train enthusiasts big and small for this event, complete with model train displays and kiddie train rides. (H-F Park District Auditorium, 2010 Chestnut Road, Homewood, IL, May 21, 9am. Free)

13. Memorial Day Parade. This city loves its parades, and perhaps no one gets more excited about cars, floats and marching bands than kids. (Daley Plaza, Washington and Dearborn sts, May 28, 11am. Free)  

14. Bike the Drive. You'd never let your children ride bikes near Lake Shore Drive... except on this crazy day. Hundreds of bicycles take over one of the city's busiest routes during this event that benefits the Active Transportation Alliance. (Lake Shore Drive between Bryn Mawr Ave and 57th St, May 29, 5:30am. $50) 

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