Summer Festivals in Chicago for the Entire Family

by Jenny Muslin

Summer is the perfect time to visit areas of Illinois you may not typically venture to, especially because each of these locales host street festivals that offer fun for the whole family. Here are just a few of our favorite festivals to mark on your calendar! 

Old Town Art Fair, Chicago, June 13-14

These neighboring festivals are perfect to hit up together. Consistently rated one of the top art fairs in the country, the Old Town Art Fair features the work of more than 250 artists, and each year nearly half of them are new to the festival, which keeps the rotation ever-fresh. You’ll spot a craft corner for the kids, live music, and, of course, plenty of food. In addition to the numerous art booths at the festival, all of the surrounding restaurants are lively places to people-watch and many of the Old Town boutiques feature great sales. Admission: Free with $7 suggested donation for adults

Long Grove Strawberry Fest, Long Grove, June 26-28

The annual strawberry festival has become a signature Long Grove event. Live music, children’s activities, delicious food, and plenty of strawberry-flavored indulgences make for the perfect all-day outing for your family. Admission: $5

Chicago Botanic Garden Art Festival, Glencoe, July 4-5

If you live on the North Shore, you likely visit the Botanic Garden at some point during the summer. The art festival, though, is a perfect time to schedule another visit. View original works from more than 95 juried artists while enjoying the gorgeous gardens. Interactive art demos allow you to watch the artists doing what they do best. Admission: Free

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artfest Michigan Avenue, Chicago, July 10-12

This brand-new summer festival will feature original art from 150 juried artists, including activities for children and families. The three-day festival takes place along “The Mag Mile” at the base of the Chicago Tribune building, overlooking the Chicago River. You’ll experience live entertainment and amazing food from local restaurants. Admission: Free

Summer on Southport, Chicago, July 18-19

This two-day festival takes over the Southport Corridor (Waveland and Southport), showcasing incredible artists that specialize in a wide range of art, including watercolor, wood, photography, jewelry, sculpture and more. Kiddies will enjoy the children’s area filled with interactive games and activities. At night, the festival adds two main stages for live music performances from Chicago’s best bands. Don’t miss what Time Out Chicago has called one of the “Best Festivals in Town.” Admission: $5 suggested donation

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Sheffield Music Festival & Garden Walk, Chicago, July 18-19

This summer marks the 47th year of this annual festival. You’ll enjoy self-guided tours of more than 80 gardens, guided architectural tours of Chicago landmarks and homes, live music, food and a designated “Kid’s Corner.” At past festivals, the Kid’s Corner has featured a petting zoo, kiddie rides, children’s musicians, crafts and more. Adults will love the Chicago Craft Beer section where one can sample from over 100 craft beers. Admission: $7 suggested donation

Lakeshore Arts Festival, Evanston, Aug. 1-2

Situated along Evanston’s dazzling lakefront, Lakeshore Arts Festival is where you can delight in fine art from more than 100 artists in 11 categories. A variety of live music, silent art auction, and children’s craft tent will keep your day jam-packed. For delicious bites, choose from a variety of excellent local food vendors. Admission: Free

Retro on Roscoe, Chicago, Aug. 7-9

This festival is always a favorite among Chicago locals. Celebrating its 20th year, there’s something to satisfy each member of your family within the six-block fest. Enjoy live music, sensational food, antique vendors, local merchants, family-friendly activities and an Antique and Classic Car and Motorcycle Show. You’ll spot a line-up of food trucks, a plethora of strollers, and plenty of dogs, all while rocking out to classic ‘70s and ‘80s covers. Admission: $10 suggested donation 

Art at the Glen Town Center, Glenview, Aug. 8-9

The boutique-lined Glen becomes an outdoor marketplace during the 12th annual Art at the Glen. More than 185 juried artists showcase their talents and sell their artistic wares, from furniture to paintings to ceramics. Live music and kids’ activities such as an art scavenger hunt will satisfy the younger members of your family. With the abundance of family-friendly restaurants, you can rest your feet and break for lunch when the kiddos start getting restless. Admission: Free

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Wrigleyville SummerFest, Chicago, Aug. 8-9

Wrigleyville already has high energy in the summer, so imagine adding fantastic food and Chicago’s favorite bands to the mix. This two-day fest is the perfect time to visit the Cubs’ neighborhood and enjoy a variety of entertainment. Take in live music and yummy food while shopping from local vendors. The “Kid’s Zone” is popular among kids ages two to 12 and features a moon bounce, crafts, giant slide, face painting, mini golf and more. Admission: $5 suggested donation

Renegade Craft Fair, Chicago, Sept. 19-20

This standout Wicker Park fest is like walking into a live Etsy shop. Among the countless local artisans, you’ll find awesome one-of-a-kind handmade gifts, participate in DIY workshops and enjoy delicious local treats. A smaller Chicago pop-up of this craft fair will take place at The Hideout June 27-28. Admission: Free

Festival Safety

You can never be too safe when attending a crowded summer festival, particularly when young kids are in tow. And, for those of you whose teens will be partying at Lollapalooza, give them a few of these pointers before they go.

For parents of young children:

  • Have your child wear some sort of identification like a wristband or beaded bracelet with your cell phone number. For older children, teach them your phone number. You’d be surprised how many kids don’t have their parents’ phone number memorized.
  • Dress your child in bright, colorful clothing so you can spot them in the crowd should you have to turn to look for them.
  • Take a photo of your children in the morning so you can remember exactly what they are wearing.
  • Teach your children to scream if a stranger tries to take them somewhere. Tell them to yell something like “I don’t know you” as opposed to “put me down,” which will alert others that they are not with a parent.

For parents of children and teens:

  • When arriving at the festival, designate a meeting place in case a member of your family or group of friends gets separated.
  •  Have an exit strategy in case of an emergency. Know where the exits are and take note of these as soon as you arrive at the festival.

For parents of teens:

  • Have a festival buddy—someone who will stay with you when you have to leave the group for any reason.
  • Make sure your phone is charged.
  • Have an app like “Find My iPhone” or “Lookout” (both free) on your phone.
  • Leave valuables at home.
  • Never leave with a stranger.
  • Never accept a drink or drugs from a stranger.

Additional Summer Festivals for the Family

More ways to enjoy summer with your friends and family:

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