As Chicagoans, we absolutely live for summer and the street fests that come along with warmer temps. Summer street festival season is about to begin and we have the scoop on the outdoor parties both kids and parents will love. Have a blast with art, cars, animals and music. . . and that’s just the start! Get your sunnies, floppy hats and sunscreen prepped and scroll through our list to make it a summer of festivals in Chicago!
MAY
JUNE
Winnetka Children's Fair
The Winnetka Children’s Fair is celebrating its 75th anniversary! Conceived as a fundraiser in 1945, the Children’s Fair has grown to become one of the most treasured childhood events to Winnetka residents. The event includes mini-golf, family-friendly music, an instrument petting zoo, a giant fun slide, pony and camel rides, a climbing wall to challenge older kids, inflatables for all ages, arcade games and much more.
Jun. 9-11; Village Green, 525 Maple St., Winnetka; Online: winnetkacommunitynurseryschool.org
Andersonville Midsommarfest
Midsommarfest takes place in the heart of Chicago's historically Swedish neighborhood and features music, dancing, kids' entertainment and food. They have unique craft vendors and you could sample the local talent performing on 5 stages. It's always one of the highlights of Pride Month. While not solely Pride-focused, Andersonville is a diverse area that loves to celebrate its LGBTQ community.
Jun. 10-12; 5200 N. Clark St., Andersonville; Online: starevents.com
Scottish Festival and Highland Games
Travel back in time to a life on the Scottish Isles at the annual Scottish Festival & Highland Games. Your wee ones are sure to enjoy the men dressed in kilts, caber tossing, bagpipers strolling, adorable dogs dressed in Tartan, beautiful Heather queens, Haggis eating, and the shortbread contest at the Midwest’s largest Celtic Family Festival.
Jun. 17 & 18; Hamilton Lakes, 2 Pierce Place, Itasca; Online: scottishfestivalchicago.org
Exchange Club of Naperville's Ribfest
There’s a reason why this annual, finger-licking extravaganza of BBQ is so popular: Grillers come from all over the country to dish their ‘cue and compete for the festival title and the music lineup is always impressive. The Family Area is a fest unto itself with a petting zoo, magic shows, inflatables and more. This will be the first year in their new digs, having moved from Naperville after the 2019 festival.
Jun. 17-20; DuPage Event Center & Fairgrounds, 2015 Manchester Rd., Wheaton, Online: ribfest.net
Ravenswood on Tap
Ravenswood’s "Malt Row" is home to one of the country’s most prolific craft brewing communities and they celebrate that scene with their annual Ravenswood on Tap craft beer fest. This two-day event features beer and spirits from local breweries, grub from some of Chicago's favorite restaurants and food trucks, a killer lineup of live music and handmade goods from local retailers and artists.
Jun. 18 & 19; Berteau & Ravenswood Avenues, Ravenswood; Online: ravenswoodchicago.org
Logan Square Arts Festival
This late June event on the Square is an awesome art walk at the local businesses that celebrates the creativity, diversity and vitality of the Logan Square neighborhood.
Jun. 24-26; Logan Blvd. & Milwaukee Ave.; Logan Square; Online: logansquareartsfestival.com
JULY
Square Roots Festival
This fest gives you lots of reasons to twist and shout, as this fest is perfect for families that love tunes. The instrument petting zoo is always a hit with curious kids and parents love checking out some of the best craft beers in the area. Bring a bathing suit or a change of clothes so that your kiddo can enjoy the splash pad at nearby Welles Park.
Jul. 8-10; 4400 N. Lincoln Ave., Lincoln Square; Online: squareroots.org
Southport Art Festival
A favorite of many families, Southport Art Festival brings old-fashioned fun to the Southport Corridor, just a short distance from the friendly confines of Wrigley Field. When a street boasts about multiple kid-friendly restaurants and ice cream shops, you know you’re in for a good time. Throughout the day, kids can enjoy interactive games and activities that make for an unforgettable day.
Jul. 9 & 10; N. Southport Ave. & W. Waveland Ave., Lakeview; Online: starevents.com
Bucktown Neighborhood & Garden Walk
The annual Bucktown Neighborhood & Garden Walk brings the community together in celebration of urban gardening and nature. This annual walk features garden tours, musical performances, family activities and more.
Jul. 9 & 10; Online: bucktown.org
Downtown Tinley Block Party
Tinley Park's annual block party features live music, food and free family fun, including a bean bag tournament, rides and inflatables, KidZone activities and a classic car show.
Jul. 17; Zabrocki Plaza, 17375 S. Oak Park Ave., Tinley Park; Online: downtowntinley.com
Fiesta del Sol
Get a taste of Mexico at the largest Latino Festival in the Midwest. Put together by the Pilsen Neighbors Community Council, the fest draws people to the Pilsen neighborhood and raises money to provide scholarships to local youth. The children’s area encourages educational activities through read-aloud sessions, book sales and educational games. Face painting, art displays by local and national artists (including kids!) rounds out the fest and may inspire your little ones to get creative.
Jul. 28-31; 1400 W. Cermak St., Pilsen; Online: fiestadelsol.org
Jeff Fest
Jefferson Memorial Park plays host to a three-day art and music fest known for cutting edge local and national acts across all genres. The festival takes place on the grounds of Jefferson Memorial Park with two stages and a designated Kid’s Zone where they can listen to family-friendly performances and get their faces painted, jump around in bounce houses, ride ponies and more.
Jul. 29-31; Jefferson Memorial Park, 4822 N. Long, Jefferson Park; Online: chicagoevents.com
AUGUST
Vintage Days
Long Grove Vintage Days will showcase all things vintage, reclaimed, hand-made, upcycled, antique and repurposed in an open-air summer marketplace. Vintage Days gives everyone from the vintage collector to the admirer a plethora of enduring products they can’t find anywhere else. Families will especially love the penny carnival run by kids, for kids, and the complimentary tractor rides.
Aug. 6. & 7; 308 Old McHenry Rd., Long Grove; Online: longgrove.org
Retro on Roscoe
A local favorite because of its family area, Retro on Roscoe offers kids prime inflatables, delectable crafts, balloon artists, face painting, music, rides and more. Car and motorcycle fanatics love the classic cars at every turn, and the retro music from five stages is the perfect beat for taking it all in.
Aug. 12-14; 2000 W. Roscoe St., Roscoe Village; Online: starevents.com
Port Clinton Art Festival
Little artists will love this fest where they can gaze at artistic wonders (some by budding artists in the dedicated kids’ gallery) and also create their own art.
Aug. 27 & 28; 600 Central Ave., Highland Park; Online: amdurproductions.com
SEPTEMBER
Naperville Last Fling
Naperville has proven they’ve mastered the art of throwing the epic end-of-summer party with their Last Fling. Head west for this four-day affair featuring national headlining artists, a massive carnival and family-friendly events and entertainment.
Sep. 2-5; Jackson & Main Streets, Naperville; Online: lastfling.org
— Maria Chambers
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