Chicago With Kids

Windy City Hot Dog Fest
2026-05-30 - 2026-05-31 | Portage Park, 4000 N. Milwaukee, Chicago, IL, 60641, United States
Get ready for a weekend full of classic Chicago eats at the in Chicago’s Portage Park neighborhood. This family-friendly festival brings together some of Chicagoland’s favorite hot dog vendors to compete for the title of “Top Dog,” with attendees voting for their favorites. Along with plenty of Chicago-style hot dogs, the fest features live music, arts and crafts vendors, kids’ activities, a hot dog eating contest, and even a dog parade.

Free Resident Day at the Field Museum
2026-06-03 09:00 - 17:00, 2026-06-10 09:00 - 17:00, 2026-06-17 09:00 - 17:00, 2026-06-24 09:00 - 17:00, 2026-07-01 09:00 - 17:00, 2026-07-08 09:00 - 17:00, 2026-07-15 09:00 - 17:00, 2026-07-22 09:00 - 17:00 (America/Chicago) and 6 more dates | Field Museum, 1400 S Lake Shore Drive, Chicago, IL, 60605, United States
“Free Admission Days are the perfect opportunity for Illinois residents to explore our general admission exhibitions with your family or a group of science-loving friends. Or, use these days to check out special ticketed exhibitions or a 3D movie with a discounted Discovery or All-Access Pass.
Tickets for Free Days are only available to Illinois residents on-site and cannot be reserved in advance. Please ask a Visitor Services staff member for the special offer and show your Illinois proof of residency. You cannot take advantage of Free Days when buying tickets online.” -From the Field Museum Website

Cream of Wheaton
2026-06-04 08:00 - 2026-06-07 17:00 | Liberty Dr. and Carlton Ave., Liberty Dr. and Carlton Ave., Wheaton, United States
Four days of summer fun in downtown Wheaton with carnival rides, live music, food, kids’ activities, an arts & crafts fair, and more. Free admission.

Lincoln Park Greek Fest
2026-06-05 - 2026-06-07 | St. George Greek Orthodox Church, 2701 N. Sheffield Ave., Chicago, IL, United States
xperience a weekend of Greek food, live music, traditional dancing, artisan vendors, and family-friendly fun at St. George Greek Orthodox Church in Lincoln Park. Enjoy authentic Greek flavors and cultural performances while celebrating the vibrant traditions and hospitality of the Greek community.

Bitter Jester Music Festival
2026-06-05 08:00 - 17:00, 2026-06-05 17:30 - 22:30, 2026-06-06 17:30 - 22:30, 2026-06-12 17:30 - 22:30, 2026-06-13 17:30 - 22:30 | Port Clinton Square, 600-601 Central Ave, Highland Park, IL, 60035
Discover emerging musicians from across the Midwest at this free, family-friendly music festival in downtown Highland Park. Enjoy live performances spanning a variety of genres, food and drinks, and the chance to see tomorrow’s headliners before they hit the big stage. Free admission and free parking.

Deerfield Art Festival
2026-06-06 10:00 - 17:00, 2026-06-07 10:00 - 17:00 | Downtown Deerfield, 821 PARK AVE, Deerfield, IL, 60015, United States
rowse original artwork from more than 100 juried artists as downtown Deerfield transforms into an open-air gallery. Enjoy live music, artist demonstrations, interactive art activities, a Kids Art Zone, face painting, food and drinks, and plenty of family-friendly fun. Free admission.

Hinsdale Fine Arts Festival
2026-06-06 10:00 - 17:00, 2026-06-07 10:00 - 17:00 | Burlington Park, 30 E. Chicago Avenue, Hindsale, IL, United States
Explore Burlington Park as more than 80 juried artists showcase original paintings, photography, jewelry, ceramics, sculpture, and more. This free outdoor art festival also features children’s art activities, local food vendors, and a charming downtown setting perfect for a summer stroll.

57th Street Art Fair in Hyde Park
2026-06-06 11:00 - 17:00, 2026-06-07 11:00 - 17:00 | 57th Street, Between Kenwood and Woodlawn, Chicago, IL, United States
Stroll through Hyde Park and explore one of the Midwest’s oldest juried art fairs, featuring nearly 200 artists showcasing original paintings, jewelry, ceramics, photography, sculpture, and more. Enjoy live blues music, family-friendly activities, food vendors, and a vibrant community atmosphere at this free outdoor event

Art of Pride
2026-06-07 12:00 - 16:00 | Hyde Park Art Center, 5020 S Cornell Ave, Chicago, IL, 60615, United States
Celebrate Pride Month at Hyde Park Art Center with an afternoon of live performances, local artists and makers, hands-on art activities, and community-focused programming. This free, all-ages event highlights LGBTQIA+ creativity, connection, and self-expression in a welcoming and inclusive environment.

Bitter Jester Music Festival Grand Finale
2026-06-27 23:30 - 2026-06-28 03:30 | Downtown Highland Park, 2nd Street, Highland Park, IL, 60035, United States
