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Upcoming events in Chicago, IL

61 listed. Page 3 of 3

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Jun 19–20, 2027 Chicago, IL

Chicago Pride Fest

Organizer Northalsted Business AllianceUnclaimed

The 25th annual Chicago Pride Fest takes place June 20 and 21, 2026, from 11 a.m. to 10 p.m. in Chicago's Northalsted neighborhood, the weekend before the city's Pride Parade. The two day street festival features live music on three stages, drag performances, the Chicago Gay Men's Chorus, a Proud Pet Parade on Sunday at noon, and more than 150 food and merchandise vendors, with a suggested $20 donation for entry.

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Deadline not listed

Details and fees on their site

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Jul 8, 2027 Chicago, IL

Windy City Smokeout

Organizer Windy City SmokeoutUnclaimed

Chicago’s biggest country music and BBQ festival returns every July outside the United Center. Windy City Smokeout pairs live sets from the genre’s top touring artists with authentic barbecue from pitmasters across the country. A two-time ACM Festival of the Year winner, it’s been a Chicago summer staple since 2013.

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Deadline not listed

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Jul 11, 2027 Chicago, IL

Chosen Few Picnic & Festival

Organizer Chosen Few DJsUnclaimed

The Chosen Few Picnic & Festival returns to Jackson Park in Chicago on July 11, marking its 36th year celebrating house music. The one day picnic and music festival has drawn crowds of about 45,000 people, featuring DJs and performers from the Chosen Few family.

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Deadline not listed

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Jul 23, 2027 Chicago, IL

Fiesta del Sol

Organizer Pilsen Neighbors Community CouncilUnclaimed

Join us as we continue the yearly Chicago tradition of shared community and experience. Fiesta Del Sol has been a display of Chicago latino presence and community connection, as we celebrate our 54th annual, we want to honor all who have supported and been a part of Fiesta Del Sol throughout these solar returns. Fiesta del Sol is free and open to the public! Find our most asked questions about the festival. Thursday J uly 23 through Sunday July 26, 2026. Fiesta del Sol is a FREE , family-friendly festival!

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Closed May 28, 2026

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Jul 25, 2027 Chicago, IL

Chinatown Summer Fair

Organizer Chicago Chinatown Chamber of CommerceUnclaimed

The 46th Annual Chinatown Summer Fair is one of the most ethnically unique outdoor events in Chicago and the Midwest. Attracting more than 40,000 people from throughout the region, Chinatown Summer Fair is a true celebration of Far East beauty and culture including food, art and music located on Wentworth Avenue from Cermak Avenue to 24th Place in Chicago. Admission is FREE! The next Chinatown Summer Fair will be Saturday, July 24 and Sunday, July 25, 2027 ! Saturday will be from 11 a.m. to 10 p.m., and Sunday from 10 a.m. to 7 p.m. This neighborhood street festival will open with a lion dance procession at 12:30 p.m., a welcome at 1 p.m. on the main stage, followed by Asian performances, kung fu demonstrations, samplings from Chinatown’s restaurants & unique gift shops, arts & crafts exhibits, street vendors with an array of merchandise, and a children’s area–a fabulous family event...

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Deadline not listed

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Aug 22–23, 2027 Chicago, IL

Bucktown Arts Fest

Organizer Bucktown Community OrganizationUnclaimed

Stop by the info booth during the art festival to get your very own print! Whether you’re a Bucktown neighbor, Chicago student, visiting a friend, or just looking for another way to get involved–we’d love to have you! It all started one hot summer in the 80s when four artists decided to sell their art in the park. A neighborhood tradition, built by volunteers, where all proceeds go to fund arts education. At the park and in local classrooms, we make more arts education possible. A big THANK YOU to the volunteers at the Bucktown Fest this year. So well organized and very helpful through the two hot days.

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Deadline not listed

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Aug 28, 2027 Chicago, IL

Taste of Greektown

Organizer Greektown ChicagoUnclaimed

Taste of Greektown returns for its 36th year, running from Friday, August 28, to Sunday, August 30, 2026, on Halsted Street between Adams and Van Buren in Chicago. The city's largest celebration of Hellenic cuisine features the neighborhood's Greek restaurants, some open 25 to 40 years, plus live music, Greek dancing and family activities, with free admission and hours running 4 to 10 pm Friday and 11 am to 10 pm Saturday and Sunday.

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Closed Apr 29, 2023

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Aug 29, 2027 Chicago, IL

Fiesta Boricua de Bandera a Bandera

Organizer Puerto Rican Cultural CenterUnclaimed

The 33rd annual Fiesta Boricua: De Bandera a Bandera takes over Paseo Boricua in Chicago's Barrio Boriken on Saturday and Sunday, September 5 and 6, over Labor Day weekend. Admission is free, and the celebration features Puerto Rican food, live music, dancing, craft vendors, vejigantes performers and games, with the Puerto Rican municipality of Isabela honored as this year's guest of honor.

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Deadline not listed

Details and fees on their site

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