With kids out of school and summer heating up, it’s time to fill up your family summer fun list. Take the family out to some of the dozens of festivals Chicagoland is known for.

You’ll find the perfect fit, whether you have a family of art lovers, music devotees or foodies or fans of fuzzy animals and shiny cars. Looking for more fairs and fests? Check out the latest events on our calendar. 

Jump to:
June Fairs and Fests
July Fairs and Fests
August Fairs and Fests
September Fairs and Fests

June Fairs and Fests

Geneva Viking Ship, photo courtesy of Al Benson

June 19-20, 2021

Art aficionados and leisurely shoppers alike may find unique pieces spanning a wide variety of art mediums, including paintings, flat arts, jewelry, furniture, ceramics, wearables, fashion, accessories, 3D art pieces, sculptures and more. Artisans and makers will be showing and selling items from art to food, clothing to lotions, stationary to furniture, and candles to home decor.

Mexican Art at Cantigny Park

June 19-20, 2021

Cantigny Park showcases the authentic and hand-crafted work of local Mexican artists. Enjoy their creativity, talent and variety. The participating artists will be stationed throughout Cantigny Park’s newly renovated gardens and grounds.

Geneva Viking Ship

June 20, 2021

Families can learn all about this “one of a kind” ship during a docent-led tour. Discover Viking’s construction, journey and significance. Tours begin every 15 minutes and self-guided tours are available.

The Map of Now (Virtual)

June 25-26, 2021

  • Hosted by: Lucky Now Productions
  • Cost: $5-$50

This interactive digital festival pairs the aesthetics of retro video games with a turbo-charged lineup of Chicago dance, theater, music and comedy performers. Taking place in an online forum called Gather. Town, guests “roam” through virtual Chicago and as they interact at each of the venues, they’ll find pre-recorded productions created specifically for the festival. Tickets can be purchased on a sliding scale each half hour.

Long Grove Strawberry Fest

June 25-27, 2021

Experience everything from strawberry-infused creations like prime rib sandwiches lathered in strawberry salsa to classic strawberry pie-eating contests. Following the new CDC and state reopening guidelines, organizers are bringing back the full-scale event that has inspired so much fun to kick off summertime in the suburbs.

READ MORE: Long Grove Family Guide

Pride in the Park Chicago

June 26, 2021

Expanded to two days, this fest in Grant Park celebrates gay pride and the LGBT community with national and local music acts running the gamut from EDM to hip hop/rap to ’80s hits to pop. Check out health and safety requirements for entry, including downloading HealthPass+ and showing proof of vaccination or a clear PCR test.

Navy Pier Pride

June 26, 2021

Families with kids of all ages can enjoy this family-friendly event that spreads pier-wide. Social distancing measures will be in place as required by CDC and state and local governments at the time.

READ MORE: Pride Month 2021 Guide for Chicago Families

Deer Park Art Show

June 26-27, 2021

This juried fine art and craft show features dozens of artists offering jewelry, paintings, sculptures, photography, woodwork and more. Festivalgoers will enjoy live performances from a variety of musical acts on the stage, food from local restaurants and art activities for kids, including an art scavenger hunt and spin art.

Highland Park Festival of Fine Arts

June 26-27, 2021

This fest features the works of nearly 100 juried artists, music, food, art workshops and kids’ activities. Be sure to check out the Youth Art Division of the fair.

Earth Day Fair

June 27, 2021

Parents can learn green living tips and energy-saving info while kids participate in children’s activities. Eco-friendly vendors will also discuss the benefit of trees and residents can order a rain barrel or composter.

Find more June fair and fests listed in our calendar.

July Fairs and Fests

Windy City Ribfest, Photo Credit: Choose Chicago, Special Events Management,

Windy City Ribfest

July 2-4, 2021

This fest features live music, lots of ribs, arts crafts and kids’ area. Located in Uptown, the Windy City Ribfest has become a Fourth of July tradition.

Taste of Chicago To-Go

July 7-11, 2021

  • Address: Pop-up events across Chicago
  • Cost: Free

The popular annual festival is reimagined this year with food, music and dance across the city. It will feature nearly 40 eateries. Highlights include pop-up events at the Pullman City Market (July 7), Austin Town Hall City Market (July 8), The Hatchery (July 10), the West Englewood neighborhood (July 10), and Eli’s Cheesecake Company (July 10). Also watch for a special “Taste-ing” event at Goose Island Brewery’s Tap Room (July 9); an afternoon of Puerto Rican food and coffee with Marisel Vera, author of The Taste of Sugar, at ¡WEPA! Mercado del Pueblo (July 9); a Picnic in White at Millennium Park produced by women restaurateurs (July 11); and pop-up music performances at participating eateries citywide.

The Forge Movies in the Park

July 10, 2021

Watch Independence Day under the stars. Guests should bring their own chairs and blankets. Snacks and beverages will be available for sale; no outside alcohol is allowed.

Wild Fest

July 11, 2021

Experience wildlife with Big Run Wolf Ranch, Jim Nesci’s Cold-Blooded Creatures, Save Our American Raptors, Incredible Bats, K-9 Guardian Dog Demonstration and more. Concessions available for purchase.

Chicago Auto Show

July 15-18, 2021

The nation’s largest auto exposition showcases more than 1,000 domestic and imported vehicles, auto-related exhibits, competition vehicles and project, antique and collector cars. Kids can enjoy interactive displays throughout the show. The show will adhere to COVID protocol, including mask requirements, reduced capacities and social distancing.

Millennium Art Festival

July 16-18, 2021

The three-day festival, formerly known as the New East Side Art Festival, showcases more than 110 juried artists with an array of original artwork, including paintings, ceramics, photography and furniture. Millennium Art Festival blends live performances, food and interactive art-filled experiences. Families are encouraged to bring gently used art to the fest and donate it to The Chicago Furniture Bank.

Chinatown Summer Fair

July 17, 2021

This neighborhood street festival will open with a lion dance procession at 12:30 p.m. on Saturday, a welcome at 1 p.m. on the main stage and be followed by Asian performances, kung fu demonstrations. Guests can sample from Chinatown’s restaurants and shop at gift stores, arts & crafts exhibits and street vendors with an array of merchandise. Current CDC and local regulations for mask wearing and social distancing will be followed.

Belmont-Sheffield Music Fest

July 17-18, 2021

This festival, held at the busy Lakeview intersection, is teeming with top local tribute bands on the main stage, a second community entertainment stage, food and drinks. Families can enjoy arts and craft vendors and a kids’ play area.

Glencoe Festival of Art

July 24-25, 2021

More than 90 juried artists from across the country will showcase their work in a variety of different mediums including painting, photography, ceramics, glass, jewelry, and wood. Artists will be available to provide live demonstrations and booth chats. Families are invited to bring gently used art to the fest and donate it to The Chicago Furniture Bank.

Festa Italiana (Naperville)

July 30-Aug. 1, 2021

Families can enjoy live Italian and rock music, family-friendly entertainment, merchants and authentic Italian restaurants. See dancers and singers, and then feast on the best Italian food Illinois has to offer.

Find more July fair and fests listed in our calendar.

August Fairs and Fests

Photo Courtesy of Windy City Rubber Duck Derby

Windy City Rubber Ducky Derby

Aug. 5, 2021

Spectators cheer on more than 50,000 yellow rubber ducks during the annual Windy City Rubber Ducky Derby to benefit Special Olympics Illinois. Family entertainment includes face painting, games, free food and appearances by several sports mascots. Donated prizes will be provided to the adoptive parents of the winning ducks.

DOGwood Day at Lambs Farm

Aug. 7, 2021

Highlights include demonstrations, contests, vendors, scavenger hunts, music, a beer & food tent, a bone bar and more.

Printers Row Art Fest

Aug. 7-8, 2021

Art at all price points by painters, street artists, jewelers, upcycling artists, photographers, mixed media artists and more. Kids can enjoy face painting and the Youth Art Tent. In addition to art, area restaurants and bars, which line the streets, will serve up their Chicago specialties. Live music all weekend long adds to the vibe of the show.

Edgewater EdgeFest

Aug. 7-8, 2021

Features 70 food vendors, beer and sangria, live entertainment on two stages, a kids tent and activities, a dunk tank and a pet parade.

Retro on Roscoe

Aug. 13-15, 2021

Festival features local restaurants, artisans, vendors, chili cook-off and a family area with crafts, balloon artists, face painting, music, rides and more.

Evanston Art Fest

Aug. 13-15, 2021

Enjoy high-end work from more than 130 juried artists from around the country, unique art pieces will be available for purchase throughout the weekend at a variety of price points. Throughout the three-day event, art lovers will have the opportunity to see the masters at work with live art demonstrations along with one-on-one booth chats.

Chicago in Tune: Year of Chicago Music

Aug. 19-Sept. 19, 2021

Chicago In Tune is a new citywide festival celebrating Chicago’s diverse and legendary music scene and the 2021 Year of Chicago Music. This month of music will bring iconic neighborhood venues, presenting organizations and musicians from across the city together to celebrate all music genres and forms — with both free and ticketed events at clubs, concert halls and beyond.

Gold Coast Art Fair

Aug. 21-22, 2021

The award-winning Art Fair welcomes 200 juried artists from across the country to create an exceptional, shoppable weekend experience in Chicago. In 2021, festival attendees will find beautiful artwork in all mediums and at all price points, as well as artist demonstrations. Also new for 2021 is an Emerging Artist Section at the show. Families are invited to bring gently used art to the fest and donate it to The Chicago Furniture Bank.

Taste of Greektown

Aug. 27-29, 2021

Food, music and entertainment, including Greek bands, artisans and games for both kids and families. The festival will follow CDC and local guidelines for masking and social distancing.

Dragon Boat Race for Literacy

Aug. 28, 2021

Teams compete in a fast-paced race on the south branch of the Chicago River in decorated dragon boats. Also, enjoy live musical and dance performances, booth vendors and special guest appearances. Proceeds are donated to promote literacy.

Find more August fair and fests listed in our calendar.

September Fairs and Fests

Hyde Park Jazz Festival, Photo Credit: Marc Monaghan

Naperville Last Fling

Sept. 3-6, 2021

Enjoy entertainment (free and ticketed), carnival, unique contests and a Family Fun Land at Naper Settlement with pony rides, petting zoo, Bounce Town, family stage, crafts, food and beverages, and a family-focused business expo. Proceeds are given to nonprofit organizations throughout DuPage County.

Taste of Polonia

Sept. 3-6, 2021

Features four stages of music with more than 30 performances including classic rock, pop, polka, classical, Latin and more, Polish cuisine, arts and crafts, carnival, and a Kids World featuring activities and entertainment. There will also be beer and a casino.

Winnetka Music Festival

Sept. 11, 2021

Performances from up-and-coming national and local music acts will be in the spotlight. Venue includes a family stage for acts for younger listeners.

Truck Off: Food Truck Festival

Sept. 11, 2021

All ages can snack from 40 food trucks at the Truck Off festival, which will feature live music, family-fun events and a beer tent. The food trucks range from world cuisine to classic American eats.

Oakbrook Art Festival

Sept. 11-12, 2021

Showcases the work of more than 40 juried artists from across the country in a variety of mediums, highlighting jewelry, fashion, glass and functional art, as well as painting and photography. Along with artwork available for purchase, attendees will be able to interact with artists through demonstrations and booth chats.

Naper Pride Fest

Sept. 11-12, 2021

Naperville celebrates its LGBTQ community at this fest for all ages. Enjoy a music concert on Friday night followed by a full-day festival with food, music, artisans and family activities on Saturday.

LaGrange Pet Parade

Sept. 18, 2021

Address: LaGrange Pet Parade, West Cossitt Avenue and South Park Road, La Grange

Cost: Free

Featuring marching bands, kids showcasing their pets (participate for a chance to win one of the many prizes), floats and clowns. Visit event website for participation registration.

West Loop Art Fest

Sept. 18-19, 2021

Enjoy four blocks of art as more than 100 talented artists showcase and sell creative work. Live art demonstrations will give festivalgoers the unique chance to see the masters at work. Plus, enjoy local food, live music and interactive features including a graffiti wall, Art Bingo and photo booth.

Lakeview Taco Fest

Sept. 18-19, 2021

The taco gets the spotlight treatment at this fest in the heart of the Southport Corridor. In addition to tacos and music, features beer and taco pairings, Mexican wrestlers, a kids’ activity area and arts/crafts.

Hyde Park Jazz Festival

Sept. 25-26, 2021

Festival features the finest in local jazz and national and international jazz artists, diverse performance venues, outdoor dance floor, food/beverage vendors and picnic areas, artisan vendors and activities for kids. All 2021 programs will take place in keeping with the latest State and City recommendations for live gatherings.

Find more September fair and fests listed in our calendar.

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By Harmony