Editor’s Note: Plans are changing daily for Chicago’s street fest season

As of press time, this was the most current information on these fests. We will revisit this story as new information becomes available throughout the season, so bookmark this story and keep checking in!

As Chicagoans, we absolutely live for street fest season. A vast majority were canceled last year due to Covid and plans for this year are up in the air for some, while others are moving full-steam ahead. We checked in with your favorite summer street fests in Chicago to get the current scoop for 2021. Get your sunnies and sunscreen prepped and scroll through our list to make it a summer of festival fun!
photo: OkBok via Pixabay In-Person Events Still Planned

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.

May 21-23
1000 W. Armitage Ave., Lincoln Park
Online: starevents.com

Northbrook Art in the Park
This free-entry fest takes place under beautiful oak trees in Northbrook's Village Green Park. Juried artists from across the country will be showcasing original work in a variety of mediums, including painting, photography, ceramics, glass, jewelry and wood.

May 22 & 23
Village Green Park, Shermer & Meadow Roads, Northbrook
Online: artintheparknorthbrook.com

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. 24-27
Main St. & First St., Geneva
Online: genevachamber.com

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.

Jul. 1-Jul. 4
Deer Park Crossing, 1050 W. Romeo Rd., Romeoville
Online: ribfest.net

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. 10 & 11
Southport Ave. & 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. 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. 17 & 18
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. 18
Oak Park Ave., from 171st St. to Hickory St., 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. 29-Aug. 1
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. 30-Aug. 1
Jefferson Memorial Park, 4822 N. Long, Jefferson Park
Online: chicagoevents.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. 28 & 29
Port Clinton Square
1st St. & 2nd St., Highland Park
Online: amdurproductions.com

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. 13-15
2000 W. Roscoe St., Roscoe Village
Online: starevents.com

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. 3-6
Jackson & Main Streets, Naperville
Online: lastfling.org

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. In the past, the event has included 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.

Dates TBA for a September Fest
Village Green,  525 Maple St., Winnetka
Online: winnetkacommunitynurseryschool.org


Options Still Being Considered

Andersonville Midsommarfest
In past years, this event which takes place in the heart of Chicago's historically Swedish neighborhood, included music, dancing, kids' entertainment and food. They had 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. No announcements have been made for this year's fest. Online: andersonville.org/midsommarfest

Pilsen Food Truck Social
This event, which typically takes place the first full weekend in June, is a dream for food truck fans. Plans have not yet been announced for 2021 as they are waiting to see how the COVID situation progresses. Online: pilsenfoodtrucksocial.com

Homewood Rail Fest
Train enthusiasts get a kick out of this 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. Online: village.homewood.il.us

BOING! Family Fest
Chicago Children's Theatre's BOING! Family Fest has helped families spring into summer for the last 5 years! They partner with artists and musicians to give families a one-of-a-kind lineup of music, interactive performances, games, puppetry and more! Details for this year's fest have not been announced. Online: chicagochildrenstheatre.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. Online: logansquareartsfestival.com

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. Online: ravenswoodchicago.org

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. Online: tasteoflincolnchicago.com

Pilsen Fest
Pilsen Fest hosts their annual event 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 are 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. Online: pilsenfestchicago.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. 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. Online: scottishfestivalchicago.org

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. Online: squareroots.org

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. Online: longgrove.org

photo: Isakarakus via Pixabay Cancellations Announced for 2021

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. Online: eyestotheskies.org

Franklin Park Fest
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.` Online: villageoffranklinpark.com

Webster Kids Block Party
Little Beans Cafe & Bubbles Academy have not announced plans for their summer fest. 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! Online: bubblesacademy.com

— Maria Chambers

Photo: Brett Sayles via Pexels


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