Chicago's Best Summer Festivals

Posted: June 12, 2022

Chicago has the best festivals, and we've gathered some of the Chicago's favorite summer festivals for kids and families. There are festivals and fairs taking place every weekend this summer, both in Chicago and in the suburbs and surrounding areas near Chicago. And you can find even more festivals and other events in our Calendar of Events!

June 18-19
Gold Coast Art Fair
Grant Park, S Lake Shore Dr. & E Monroe St., Chicago
This award-winning, family-friendly art fair welcomes 200 juried artists from around the country and draws thousands of art enthusiasts from Chicago and beyond, creating an exceptional, shoppable art experience. Paintings, sculpture, jewelry, ceramics, mixed media and more will be exhibited and available for purchase, and live music stages will provide entertainment in various locations, along with delicious food. All ages. Sat 10-5, Sun 10-5. Children 12 and under are free. Over 12 $10.
Learn more...

June 24-26
Long Grove Strawberry Festival
Downtown Long Grove, Routes 53 and 83, Long Grove
This festival is fun for the whole family, with food from the shops restaurants and vendors set up on the streets, live music and more. Attendees of all ages can expect three days of strawberry-infused foods and drinks, family games, and live music. All ages. June 25, 12pm-11pm June 26, 10am-11pm June 27, 10am-6pm. $5 per guest, kids under 6 free. Learn more...

June 24-26
Logan Square Arts Festival
Logan Square, Milwaukee and Logan, Chicago
The Logan Square Arts Festival features two stages of live music, food, drinks, and a renewed focus on creating a one-of-kind experience in one of the most iconic green spaces in the city of Chicago. The LSAF is three-day celebration of the diversity and vitality of our neighborhood, and it all takes place on first official weekend of the Summer. All ages. See web site for schedule. Free. Learn more...

June 25-26
Chicago Food Truck Summer Festival
South Loop, 1700 S Wabash Ave., Chicago
We have enjoyed some fun years hosting one of America's top food truck festivals. Experiencing an amazing gathering of mobile chefs preparing a range of culinary creations. All the while bringing together Chicagoans and foodies throughout the country for a peaceful family day to taste and enjoy Chicago eats. All ages. 11:00am to 7:00pm. FREE. Learn more...

July 8-10
Square Roots Festival
Lincoln Square, 4400-4560 N Lincoln Ave., Chicago
Square Roots brings together the best of Lincoln Square, Chicago, and beyond, with live music, family fun, local restaurants and vendors, and the best craft beer showcase of any Chicago street fest. More than 50 acts will appear on 4 stages, and food will be served up from a variety of Lincoln Square restaurants. All ages. See web site for schedule. Suggested Donation $10 Adults; $5 Seniors over 65 and Children under 12. Learn more...

July 8-10
West Fest
West Town, 1800-2000 W. Chicago Ave., Chicago
West Fest Chicago presents neighborhood retailers and restaurants, plus local fine artists and makers as vendors. The event also features Pet Fest with dog activities for charity, and Kid Fest with family activities and live entertainment, and more. West Fest Chicago reflects the eclectic West Town community, and is also renown for cutting edge live music programmed by Empty Bottle Presents, plus the ever popular West Fest Chicago House DJ stage. All ages. Friday 5-10pm, Saturday and Sunday 12pm-10pm. $10 optional donation. Learn more...

July 9-10
Southport Art Fest
Southport Corridor, Waveland and Southport, Chicago
This two-day festival will showcase some of the city’s best and most diverse artists. Families will have the opportunity to bring their children and enjoy all that Southport Art Fest has to offer. A special Kid's area has been designed with interactive games and activities that will make for an unforgettable time. All ages. 10am - 7pm. Free. Learn more...

July 9-10
West Loop Summer Fest
West Loop, Washington Blvd. & Sangamon St., Chicago
Haymarket Center is bringing the beach to the West Loop for this year’s West Loop Summer Fest. From sand (you heard right) to festival yacht-rock and tropical-inspired tribute bands, you’ll be uprooted to a far-off island in your own backyard. West Loop Fest grew from an annual birthday celebration for our founder, the late Monsignor Ignatius McDermott as a way to bring the community together and create goodwill among our neighbors. All ages. 12pm - 10pm. $10 Suggested Donation. Learn more...

July 15-17
Tacos y Tamales
Pilsen, 16th and Peoria St., Chicago
Authentic food, art, and entertainment return to 16th street in Pilsen. From traditional mariachis, song & dance, to the very best of Latin pop rock… the entertainment elements of the Tacos y Tamales Festival will be second to none. Patrons can expect a full weekend lineup on performance stage and into the streets where the music is as authentic as the food, culture, and pulse of the fest itself. All ages. See web site for schedule. FREE. Learn more...

July 22-24
Taste of Lincoln Avenue
Lincoln Park, 2500 N Lincoln Ave., Chicago
Taste of Lincoln Avenue offers plenty of food and arts and crafts vendors, and one main music stage with amazing regional and local entertainment. All ages. Noon - 10pm. Free. Learn more...

July 29-31
Jeff Fest
Jefferson Memorial Park, 4822 N Long Ave., Chicago
Get down to great tunes, tasty foods, family fun and more at the 21st annual summer happening that is Jeff Fest (aka Jefferson Park Arts & Music Festival). Beyond music and food, the Kids’ Zone area on the north side of the park features a ton of cool activities for families. It’s also where one will find the fest’s groovin’ "Community Stage." All ages. Friday 5-10, Saturday and Sunday 2-10. 12 and under free with paying adult; Adults $7. Learn more...

August 12-14
Retro on Roscoe
Roscoe Village, Roscoe and Damen, Chicago
Go back in time with music enthusiasts, families, and gearheads for a back in the day weekend. Three stages will be spread amongst an eminent six-block stretch in Chicago’s favorite Roscoe Village. After eating some small bites make sure to head over to the family area that offers prime inflatables, delectable crafts, balloon artists, face painting, music, rides and more. All ages. See web site for schedule. $10 suggested donation. Learn more...

August 20-21
Chicago Air and Water Show
North Avenue Beach, 1600 North, Chicago
The Chicago Air and Water Show presented by the City of Chicago is the largest FREE show of its kind in the United States. The show can be viewed along the lakefront from Fullerton to Oak Street, with North Avenue Beach as the focal point. All ages. 10am - 2pm. Free. Learn more...

August 26-28
Taste of Greektown
Greektown, 100-400 S. Halsted St., Chicago
A mix of local Greektown businesses and food vendors will provide refreshments and authentic Greek cuisine, like feta, tzatziki and roasted chicken, so Windy City foodies can experience traditional Mediterranean dishes. Lively Greek bands, dance troupes, local musicians and The Jesse White Tumblers will perform throughout the weekend. All ages. Friday 4-11, Saturday & Sunday noon-11. Free. Learn more...