Family-Friendly Festivals Near Chicago You Can’t Miss This Summer

If you’re one of the million or so parents in the Chicago area like myself, you’ve been so busy shuttling kids to camps and activities that you can barely comprehend we are already halfway through the school break and great weather. Rest easy! There’s still plenty of time and many places to take your children to make the most of the warm-weather months.

Why not start by swinging by a few neighborhood festivals, where bouncy houses, salty corn on the cob, face painting and maybe a beer tent will keep everyone in the family happy for a few hours? Here are a few family-friendly fests you can’t miss in the last half of summer.


18-22: In its 150th year, the Kane County Fair in St. Charles is a bang-up time, literally. With bull riders, a demolition derby, barrel racing, and Bengal tigers in one area; live music on the soundstage; and loads of rides, pig races, car shows, and kiddy entertainment; it is a high-energy way to spend your day.

20-22: Everyone’s in heaven at Tacos y Tamales Festival in the Pilsen neighborhood. Once you’re all blissed out on churros and tacos, tap the tequila tasting, mariachis and musical tributes to Celia Cruz, Selena, and Santana.

20-22: Ben Fest was named one of the city’s best family festivals, and for good reason. This festival is packed full of inflatables, fun sports competitions, and games that will keep kids laughing and playing while grown-ups enjoy beer tasting, burgers, and bands.

20-22: If Pitchfork Music Festival is a must-do on your list, grab the kids and their noise-muffling headphones and head over to the Kid Zone, where families can take classes, try out instruments, paint and get inspired by new and emerging bands.

20-22: Introduce your kids to your jams at the Forest Park Music Fest, where cover bands get the crowds dancing and reminiscing.

26-29: Proud American Days in New Lenox began 34 years ago with a two-man band, a keg, and a tent. Today, it boasts bands, bags tournaments, carnival rides and a tribute to military and first responders.

28-29: Taste of Lincoln Avenue lines up the tribute bands, specialty tastings, and kid activities.

Sing along, dance or just wind down at the Grant Park Music Festival, Millennium Park Summer Music Series, and Lincoln Square’s Summer Concert Series, each with shows through August.


2-5: Lollapalooza is the quintessential Chicago summer scene and can be a real moment for families with kids who can handle crowds and the sounds of competing stages. If you’ve already scored tickets, map out the bands you want to see and a plan for where to meet when (not if) you get separated. If you don’t have your wristbands, scour your friends’ Facebook feeds and ticket sites to see if you can grab passes.

The Kizapalooza zone is pretty epic, with lots of musicians swinging by to take the stage for little fans and their parents. There are also instrument demos, rocker makeovers and other fun ways to cool off and calm down while still feeling like part of the festival.

If your kids are older and into it, this is a great time to show off how cool you actually are for taking them to see Khalid, Bruno Mars and The Weeknd on the main stages and more obscure bands, DJs, and musicians in other corners of Grant Park.

3-5: Jeff Fest is as diverse and friendly as its neighbors, with Irish cloggers, Polynesian dancers, music, crafts and lots of food, all in a bring-your-own-lawnchair park setting.

4: Because Chicagoans can’t grow up without gobbling up brisket and brats, you will want to take them to the Rogers Pork Barbecue, Arts & Music Festival. One day only, rain or shine.

10-12: Hone in on your children’s hot dog appreciation at the Chicago Hot Dog Fest’s celebration of meat, baseball, and blues. Stop by a talk on hot dog history in between your no-ketchup delights. Not to worry, all those dogs and sodas and elephant ears will settle just fine with a few rounds in a bouncy house in the kid zone.

10-12: Ginza Holiday Festival is one of Chicago’s most honored family festivals. Celebrate Japanese culture with mesmerizing Taiko drum, martial arts and Minoyo folk dance demonstrations, as well as mouth-watering chicken teriyaki, udon noodles, spam musubi, and shaved ice.

10-12: Festival Cubano in the Belmont Cragin neighborhood has a line-up of get-up-out-of-your-seats musicians. The experience also includes an incredible vintage car show, dominoes tournament, carnival rides, hand-rolled cigars and a boxing corner with matches and fitness classes.

11: The Bud Billiken Parade and festival celebrates the legacy of the Chicago Defender’s legacy diversity, credibility, representation of African American Chicagoans and care for children. Everyone in the family can cheer for the dance and drill teams, marching band battles, and kids who travel from across the country to compete, connect and participate in the parade.

11-12: If it is nearly impossible to please every picky eater in your home with one dish, you’ll love taking the whole family to the Near North Food Truck Social. Pass out the cash to fend for (and feed!) yourselves with dumplings, deep dish, donuts and whatever delights appear from the truck windows.

17-19: Edison Park Fest is not just any fest on the blocked-off streets of the city. It is also a community fundraiser that helps support free local programs, events, and groups.

18-19: You cannot escape the Chicago Air and Water Show, whether you’ve got a prime seat on the beach to watch or are stuck in a downtown cubicle and can hear the roar of the planes when pilots practice the day before the big event. Free admission is a plus, but squeezing in, parking and public transportation can be tricky. Plan well, or finagle an air-conditioned view from a friend’s downtown office or apartment.

22-26: Immerse your family in farm and fun at the Will County Fair in Peotone. Swing by the 4-H exhibits, on to the carnival rides and around to the tractor and truck pull competitions.

24-26: Savor the saganaki, gyros, wine, dancing and Hellenic pride at Taste of Greektown.

31-Sept. 3: Taste of Polonia in Jefferson Park is the largest Polish festival in the country. With a casino, four stages hosting more than 30 bands, tons of food and drink, cooking classes, inflatables and even Disney character appearances, this is the place to live it up before the kids go back to school.


1-2: Cider & Sliders Festival in Lakeview is here to kick off autumn. In its inaugural year, this festival promised 50+ ciders, delicious mini-burgers and lots of crafty stuff to keep the full-bellied kids happy.

7-9: German American Oktoberfest in Lincoln Square kicks off with a Steuben parade and German mass. Not to worry, the beer flows soon after, and there’s always live music, food vendors, games and plenty of neighbors and school friends with whom you can raise a commemorative stein or hand-pulled root beer well into the evening.

7-23: World Music Festival is a multi-venue, 11-day jubilee hosted by the city, bringing 650 artists and ensembles to perform for more than 650,000 audience members in the last 19 years. Check the site for free performance schedules and locations.

15-16: Ravenswood Artwalk opens the doors of local artist studios, galleries and shops to wander through and experience. There’s also plenty of craft beers and food for purchase, vendors to peruse and music to enjoy. Follow the stream of strollers to find your way.

15-16: Printers’ Row Art Fest is a great place for families to experience dynamic artistry. The juried show and exhibitions include up-cycling and mixed media artists, photographers, jewelers, painters and street artists.

21-23: Apple Fest calls city-dwellers and suburbanites alike to Long Grove for a charming, family-centered pop-up orchard lined with seasonal treats, pie-eating contests, tug-o-war, music, and dancing.

22: Get your kids a front-row spot to the Creative Youth Festival in the Loop, where they will applaud and be inspired by talented teens performing dance, drama, spoken word, and visual arts. Check the site for details.

28-30: Oktoberfest Chicago in Lakeview is your last big hurrah before the down coats come out. Adults can enjoy Craft Brew Night while kids kick it at KinderFest. Do some polka, eat too many pretzels and pop over to see the German band Oompah.

Written by Jessica Ashley
Jessica Ashley is a writer, coach and the voice of Single Mom Nation and its sister podcast. She wears inappropriately high heels to the playground, is mom to a teenager and a threenager and lives with her chef boyfriend on the north side of Chicago.