Chicago's Best Summer Festvals

Posted: June 13, 2019

Summer's Best Festivals

Chicago has the best fests, with fun taking place every weekend! We've gathered our top picks below, and you can find even more festivals and happenings in our Calendar of Events.

June 7-9
Andersonville Midsommarfest
Clark and Foster in Andersonville
Midsommarfest gathers enthusiastic Chicagoans along Clark Street between Foster and Catalpa for two days and three nights of music, dancing, kids' entertainment, and delicious food. Handmade artists and merchants from around the region sell their wares to passersby, local shops and restaurants welcome the warm season with specials and sales, and dance troupes, DJs, and longtime favorite bands keep the party going. All ages. See web site for schedule. $10 donation at the gates; kids under 12 and seniors are free. Read more...

June 8-9
Old Town Art Fair
Old Town Triangle Historic District, Lincoln Ave and Wisconsin, Chicago
At this year's Old Town Art Fair, there will be 250 nationally acclaimed artists, an estimated 30,000 art lovers, a Garden Walk, Live Music, Food Court and Children's Corner. The Children's Corner is located on Wisconsin and Sedgwick and lets kids unleash their inner artist! There's fun for the whole family with Mad Science, Chess Wizards, Face Painting, plenty of arts and crafts and more. All ages. Gates open Saturday 10:00 am to 7:00 pm and Sunday 10:00 am to 6:00 pm, rain or shine. $10 per adult is kindly requested. Children enter free. Read more...

June 15-16
Custer Fair
600 N. Main St., Evanston
Over 300 local and regional artists, craftspeople, and commercial vendors come together over Father's Day weekend to exhibit and sell paintings, ceramics, pottery, photographs, jewelry, graphic arts, wearable art, country and home craft, antiques and collectables. Over 30 food vendors offer a full international menu, and there will be entertainment on three stages. The Arena Stage features theatre, music, and novelty performers from Chicagoland, and is perfect for families, as is the Kids Carnival. All ages. 10:00am-9:00pm. FREE. Read more...

June 21-22
Strawberry Fest
Old McHenry Rd., Downtown Long Grove
Experience everything from strawberry-infused creations like prime rib sandwiches lathered in strawberry salsa to classic strawberry pie-eating contests. For those who like to mix it up, chef-driven barbecue and other decadent local treats offer something for every taste bud. And when it comes to entertainment, Strawberry Fest leaves nothing to the imagination either, with a classic carnival, multiple stages of live music, and the Kids Zone featuring enduring family activities at no charge. All ages. Fri 12-11pm; Sat 10am-11pm; Sun 10am-6pm. $5 per day for over 12. Read more...

June 28-30
Logan Square Arts Festival
Logan Square, 2600 N. Milwaukee, Chicago
The Logan Square Arts Festival is a three-day celebration of the diversity and vitality of Chicago's Logan Square neighborhood. The festival features two stages of live music, visual art, performance art, dance, food, and drinks, in the heart of Logan Square. Each year the festival features artists of varying disciplines, neighborhood restaurants, and locally produced beer and cocktails. The festival partners with neighborhood art organizations on the presentation of visual art across the festival grounds and the performance of a diverse array of music across two stages. All ages. See web site for schedule. FREE. Read more...

July 6-7
West Fest Chicago
West Town, 1800W - 2000W Chicago Ave., Chicago
West Fest Chicago features neighborhood retailers and restaurants, fine artists, crafters, and more, reflecting the eclectic and hip West Town community. Kid Fest is 12-7pm on Saturday and Sunday on Wolcott and offers quality children and family activities including train rides, bounce houses, an inflatable super slide, pony rides, carnival games, kid friendly vendors, and a kid's stage with live family friendly music. And Pet Fest is 12-6pm Saturday and Sunday sponsored by Canine Crews. All ages. Fri 5pm-10pm; Sat-Sun 12pm-10pm. $5 donation. Read more...

July 12-14
Square Roots Festival
Lincoln Square, Lincoln between MOntrose and Wilson, Chicago
This truly local festival features neighborhood food and regional craft beer, as well as unique and exciting market vendors, while over 70 bands and artists from around the world entertain on 4 stages. Square Roots has music and fun for kids of all ages, from toddlers to teens - you'll find plenty to do with a great collection of activities, music, and dance in the Kid Zone, at the Old Town School Education Tent, and all around the festival. Family fun is Saturday, July 13th, 12:00 - 6:00 PM and Sunday, July 14th, 12:00 - 6:00 PM. All ages. $10 for adults, $5 seniors/kids, and $20 for families. Read more...

July 13-14
Roscoe Village Burger Fest
Roscoe Village, 2000 W Belmont Ave., Chicago
More than a dozen local restaurants will be throwing the tastiest party around when Roscoe Village BurgerFest returns for its 13th mouth watering anniversary. Featuring two stages of non-stop music, artists and merchants, and a fun filled Kid's Zone with a large arts and craft tent with activities. For older kids there will be rock climbing, miniature golf, jousting, inflatables, and games. All ages. 11am - 10pm. See web stie for admission details. Read more...

July 19-21
BenFest, 2215 West Irving Park Road, Chicago
It's three days of family fun including great bands, cuisine from local restaurants and tons of activities for the kids. Kids' Activities Wristband includes: Inflatables - Water slide, Basketball Challenge, Blackhawks Hockey Hot Shot, Super Giant Tic Tac Toe and Connect 4, Skee Ball Alley, Football Challenge, Grand Slam Baseball and Baseball Bat Ring Toss. All ages. Friday, 4:00 PM - 10:00 PM Saturday, 1:00 PM - 10:00 PM Sunday, 1:00 PM - 7:00 PM. $5 donation; Kids 5 and under are free. Read more...

July 25-28
Chicago Ridge Fest
Chicago Ridge, 6252 Birmingham St., Chicago Ridge
This southside summer tradition features great food, rockin' entertainment, and fun for the whole family. Merchant Lane features everything from hand-crafted items to light-up toys, and there will be plenty to eat with food brought to you by Restaurant Row, with something for everyone from burgers and fries, to funnel cakes and ice cream. All ages. See web site for schedule. FREE. Read more...

July 27-28
Taste of Lincoln Avenue
Lincoln Park, 2400 N. Halsted, Chicago
In addition to lots of great food, the festival includes two stages of great music featuring both national and regional acts. For families there's the wildly popular (and free entry) "Kids' Carnival" area open each afternoon that features entertainment, art activities, pony rides, kiddie rides and more. And new this year, a fun stand-alone "Chocolate Fest" area with tastings and sales. All ages. Noon - 10pm. $10. Read more...

August 2-4
Jeff Fest
Jefferson Memorial Park, 4822 N. Long Ave., Chicago
Get down to great tunes, tasty foods, family fun and more at the 19th annual summer happening that is Jeff Fest. 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" with eclectic acts ranging from Polynesian dancers and Irish cloggers to local bands and more. There are also arts & craft vendors, plus ticketed wine tastings that make for relaxing weekend afternoons in one of Chicago's coziest neighborhoods. All ages. Friday 5:00-10:00 pm; Saturday 2:00-10:00 pm; Sunday 2:00-9:00 pm. $5. Read more...

August 9-11
Chicago Hot Dog Fest
Chicago History Museum, Clark St. at North Ave., Chicago
Take a bite out of Chicago history at Chicago Hot Dog Fest, presented by the Chicago History Museum. The fest returns to Lincoln Park this August to include a full lineup of bands, hot dog and city history speakers, and the star of the event: Vienna Beef hot dogs prepared in various regional and ethnic styles by the city's top hot dog vendors. All ages. Fri/Sat 11am - 9pm, Sun 11am-8pm. $5 Suggested Donation. Read more...

August 9-11
Retro on Roscoe
Roscoe Village, 2000 W. Roscoe, Chicago
The beautiful tree-lined streets of Roscoe Village will set the scene for live music, artisans, antique vendors and cool merchants. Roscoe Village's top restaurants will serve up much-desired summer treats that. The family area offers prime inflatables, delectable crafts, balloon artists, face painting, music, rides and more. All ages. Fri 5-10pm; Sat and Sun noon - 10pm. $10 suggested donation. Read more...

August 15-18
Chicago's Little Italy Festival
Little Italy, 1431 W. Taylor St., Chicago
Chicago's Little Italy Fest-Taylor Street celebrates the great history of the neighborhood by celebrating the rich culture of the generations of Italians who settled there decades ago. Fabulous food from award-winning area restaurants, several stages of continuous family entertainment, quality merchandise from Italy and colorful cultural attractions make this event one of the most popular of the summer. All ages. Thurs: 5-10PM; Fri: 5-11PM; Sat: Noon-11PM; Sun: Noon-9PM. $10 suggested donation. Read more...

August 30 - September 2
Port Clinton Art Fair and Taste of Highland Park
Central Ave. between First and Second Streets, Highland Park
This year's 12th Annual Taste of Highland Park will run in conjunction with the 35th Port Clinton Art Festival in the heart of Downtown Highland Park. This event will feature local Highland Park restaurants, live entertainment all day long, and 300 artists selling original work in the Port Clinton Art Festival. Taste dozens of different cuisine, groove to your favorite songs, and be enlightened by the original art of artists from around the world. All ages. Friday 5-10pm, Saturday 10am-10pm, Sunday 10am-6pm. FREE. Read more...

Find more summer fun and festivals in our Calendar of Events.