Grab your sunnies and sunscreen—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 folk music. . . and that’s just the start! Scroll down and get ready for a summer of festival fun.

photo: courtesy of North Charleston via flickr


Northbrook Art in the Park
Previously scheduled for Memorial Day Weekend, Northbrook Art in the Park is hosting a virtual event giving visitors real-time access to 42 independent artists via Zoom chat to shop their curated collections. Live music and event hosts will also be running during this time for guests to enjoy and shipping on all purchases is free. The festival’s curated selection of art ranges from fine art, wearable fashion, paintings, 3D pieces and more.

Virtual event hosted Jun. 6, noon-4 p.m. (pieces available online through Jun. 13)

Andersonville Midsommarfest
Andersonville is taking its fest virtual for 2020. This one-night-only event will take place the weekend in which the 55th annual outdoor Midsommarfest was previously scheduled. Andersonville at Home: A Midsommarfest Experience & Fundraiser will stream on Facebook Live with a pre-show at 6 p.m. and the main event beginning at 7 p.m. with appearances by some of the most popular local performers, including kid-favorite Laura Doherty Music.

Virtual event Jun. 12, 6 p.m.
Cost: please consider donating via Venmo
Online: &

BOING! Family Fest
Spring into summer at BOING! Family Fest, Chicago Children’s Theatre’s 4th annual family-friendly festival that’s going virtual this year. They’ve partnered with theatre artists and musicians all over the country to bring you a free one-of-a-kind line-up of music, interactive performances, games, puppetry and more. Any donations will benefit the Red Kite Project, Chicago’s original (and internationally-known) theatrical and educational experiences for youth on the autism spectrum.

Virtual event Jun. 20, 10 a.m.
Cost: Free, but donations appreciated

Ravenswood on Tap
Ravenswood’s “Malt Row” is home to one of the country’s most prolific craft brewing communities and they’re celebrating that scene at the third annual Ravenswood on Tap craft beer festival! This two-day outdoor 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. 22 & 23; Sat. noon-10 p.m. & Sun., noon-6 p.m.
Ravenswood & Berteau Ave., Ravenswood
Cost: $5 suggested donation; $7 drink tickets


Southport_020 copyphoto: Summer on Southport / Raney Images

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. 13 & 14; Sat. & Sun., 10 a.m.-7 p.m.
Southport Ave. & Waveland Ave., Lakeview
Cost: Suggested donation of $5


TOLA-kids-artphoto: Taste of Lincoln Avenue

Taste of Lincoln Avenue
This popular fest sprawls over several city blocks in the heart of Lincoln Park and has so many attractions, including 250-plus vendors, food and more than 35 acts on three music stages. Afternoons include a stand-alone Kids Area (on Montana, from Sheffield to Lincoln Ave.) featuring art activities, inflatables, magicians, games and more.

Jul. 25 & 26; Sat. & Sun., noon-10 p.m.; Kids Carnival, Sat., & Sun., noon-6 p.m.
Lincoln Ave. & Fullerton Ave., Lincoln Park
Cost: Suggested donation $10 benefits the Wrightwood Neighbors Association; kids carnival is free if you enter on Halsted (rides cost extra)

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. 31-Aug. 2; Fri., 5 p.m.-10 p.m.; Sat., 2 p.m.-10 p.m.; Sun., 2 p.m.-9 p.m.
Jefferson Memorial Park
4822 N. Long, Jefferson Park
Cost: $5/person; Free for children under 12 and those named Jeff!

RetroRoscoe_043 copy (1)photo: Retro on Roscoe / Raney Images

Retro on Roscoe
A local favorite because of its family area, Retro on Roscoe fences off its kids’ area from the rest of the fest so you can relax while your little ones rock out to bands on the family stage, bounce in inflatables or create artistic masterpieces. Car and motorcycle fanatics love the classic cars at every turn, and the ‘80s music from six stages is the perfect beat for taking it all in.

Aug. 9-11; Fri., 5 p.m.-10 p.m., Sat. & Sun., noon-10 p.m.
Roscoe St. & Damen Ave., Roscoe Village
Cost: Suggested donation $10

photo: Pilsen Fest

Pilsen Fest
In its 9th year, Pilsen Fest returns with a one village, one sound objective that celebrates and embraces diversity, solidarity and unity. This growing, high-energy music and arts fest reflects the community spirit and creative drive of its eclectic neighborhood. Attendees will be treated to the deep pool of cultural talent that exists in Pilsen and neighboring communities with a blend of live music, food, art, children’s activities and handcrafted goods aimed at highlighting the neighborhood’s Latino heritage.

Aug. 17 & 18; noon-10 p.m.
Blue Island, from 18th St. to 21st St., Pilsen


Homewood Rail Fest
Hey train enthusiasts, check out the Homewood Rail Fest, a train-focused fest that has something for every rail lover (and their families). Explore one-of-a-kind collections of antique trains, train memorabilia, intricate train layouts and kids can participate in train-themed crafts.

May 18; 9 a.m.-3 p.m.
H-F Park District Auditorium
2010 Chestnut Rd., Homewood

railroad-dazephoto: Franklin Park Railroad Daze

Franklin Park Fest
Hit up Franklin Park Fest for 4 days of live music. Railroad Day during Franklin Park’s Fest is one heck of a choo-choo extravaganza. Explore the interiors of over a dozen trains and check out some classic train memorabilia. Kids can take mini train rides and everyone can enjoy a carnival, live entertainment and food at this train-tastic fest.`

Jun. 6-9
Tower Park
Calwagner St. & Franklin Ave., Franklin Park
Cost: Free but ticket purchase required for rides

Winnetka Children’s Fair
The Winnetka Children’s Fair is celebrating its 74th anniversary this year! Conceived as a fundraiser in 1945, the Children’s Fair has grown to become one of the most treasured childhood events to Winnetka residents. New attractions include miniature golf, a DJ playing family-friendly popular music, and an “instrument petting zoo” provided by Bach to Rock from 10 a.m. to 11 a.m. both days of the fair, in which children can explore an assortment of musical instruments including guitars, drums and ukuleles. Other entertainment will include 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. 7 & 8; Fri., 10 a.m.-7 p.m. & Sat., 10 a.m.-3 p.m.
Village Green,  525 Maple St., Winnetka
Cost: Free entry, ticketed games & rides

Scottish Festival and Highland Games
Travel back in time to a life on the Scottish Isles at the 33rd 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. Don’t miss out because it’s sure to be a delight for all. Proceeds benefit the oldest 501(c)3 charity in Illinois, the Scottish Home and Caledonian House, now collectively known as Caledonia Senior Living & Memory Care.

Jun. 14 & 15; Fri., 1 p.m.-10 p.m.; Sat., 8 a.m.-10 p.m.
Hamilton Lakes
1 Pierce Place, Itasca
Cost: Fri., $15/adults, free for ages 12 & under; Sat., $25/adults, $12/ages 4-12, free for ages 3 & under

Evanston Custer Fair
The Piccolo Theatre leads the organization of this festival, so it’s full of surprises at every turn. . . literally! In the past, there have been fire-eaters, comedy troupes and puppet shows throughout. Take the little ones to Eiden Park for the kids’ area with balloon art, story telling, face painting and more. Leave the car at home and take Metra or the El; both stop right at the entrance to the fest.

Jun. 15 & 16, 10 a.m.-9 p.m.
Custer Ave. & Main St., Evanston
Cost: Free

geneva-swedish-days-credit-kelly-vanderploegphoto: Geneva Swedish Days

Geneva Swedish Days
This classic ode to summer has kid’s events for six straight days. Live music, carnival rides, 5K and tent with everything Swedish are just a few of the can’t-miss activities at this Swedish-inspired fest.

Jun. 18-23
Main St. & First St., Geneva
Cost: Free (cost for some activities)


eyes-skiesphoto: Lisle Eyes to the Skies

Lisle Eyes to the Skies
Here’s your chance to see a hot air balloon up close—or even ride in one! Hot air balloons rise up daily, and tethered balloon rides are available in between. There’s also a carnival and a children’s area with LEGO building, martial arts and dance performances, storytelling, music, games and animal shows. Fireworks that end the festivities every night round out this spectacle.

Jul. 4-7
1825 Short St., Lisle
Cost: $8 (children under 6 free); purchase tickets to ride carnival rides

Downtown Tinley Block Party: 125 Amplified
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. 21, noon-7 p.m.
Oak Park Ave., from 171st St. to Hickory St., Tinley Park
Cost: Free

photo: Homewood’s One Giant Block Party

Homewood’s One Giant Block Party
The Village of Homewood invites the community once again to their giant block party! Fest goers will enjoy face painting, a full line-up of live music throughout the day, jump house, games, zip line, adventure slide, crafts and much more.

Aug. 17;, 10 a.m.-9 p.m.
Martin Ave. between Ridge & Hickory Roads, Homewood
Cost: Free

4th Annual Vintage Fest
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 starting at noon both days.

Aug. 17 & 18; 10 a.m.-6 p.m.
308 Old McHenry Rd., Long Grove
Cost: Free

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. 24 & 25, 10 a.m.-6 p.m.
Port Clinton Square
1st St. & 2nd St., Highland Park
Cost: Free


— Maria Chambers & Jen Peterson

Photo: Brett Sayles via Pexels



Bucktown Neighborhood & Garden Walk
The annual Bucktown Neighborhood & Garden Walk brings the community together in celebration of urban gardening and nature. They are planning a self-guided, COVID-19 socially responsible celebration of all things Bucktown. They will provide a guide of public art, landmarks, schools, churches, parks and other notable places.

Jul. 11 & 12 (and any day after)
Cost: $5 suggested donation

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. 30-Aug. 2; Thurs., 5–10 p.m.: Fri. & Sat., 11 a.m.–11 p.m.; Sun., 11 a.m.–10 p.m.
1400 W. Cermak St., Pilsen
Cost: Free

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.

Aug. 28-30; Fri., 5 p.m.-10 p.m.; Sat., noon-10 p.m.; Sun., noon-9 p.m.; Family Fun days Sat. & Sun., noon-6 p.m.
Lincoln Ave., between Montrose Ave. & Wilson Ave., Lincoln Square
Cost: Suggested donation, $10/adults, $5/seniors & kids, $20/families

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. 4-7
Jackson & Main Streets, Naperville
Cost: Varies by activity


Webster Kids Block Party
Little Beans Cafe & Bubbles Academy are working on plans for their 4th Webster Kids Corridor Block Party. In past years, this has included an afternoon of music, demo classes, bounce houses, kids’ activity tables from favorite local partners, food and drinks, and block party fun! This event will not happen as planned on Jun. 20, but may occur later in the summer or virtually.

Bubbles Academy / Little Beans Cafe, 2184 N. Elston, Bucktown


The official start of the festival season is kicked off by Mayfest, as they celebrate all things spring and outdoors with their annual party in the streets at Armitage & Sheffield in LP. They’ve made the decision to cancel this year’s event and will be back May 28-30, 2021.


Pilsen Food Truck Social
This event that typically takes place the first full weekend in June and is a dream for food truck fans will not take place in 2020. They will be back in 2021 with a re-envisioned event.


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. They have made the decision to cancel this year’s activities and will return in 2021.


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. They were scheduled for a venue change this year, moving the festivities from Naperville to Romeoville, but you’ll have to check out their new digs in 2021.



The Ultimate Summer Bucket List for Chicago Parents