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Chicago’s June Calendar of Events

Chicago has a packed event calendar this June. There are several street fests, pride events, and art fairs.

Things to Do in Chicago in June:

Uptown Art Week

When: June 1-5, 2022
Neighborhood: Uptown
Address: throughout the neighborhood

This event celebrates public art. During the event, more than 50 new works of art will be painted live in the neighborhood. In addition, there are art exhibitions, a block party, and activities for people of all ages.

Songs that Speak

When: June 1, 2022
Neighborhood: Wicker Park
Address: The Den Theater

This event kicks off Pride month with performances of pop and musical theater songs with LGBTQ+ themes.

Do Division

When: June 3-5, 2022
Neighborhood: West Town / Wicker Park
Address: Division Street between Damen and Leavitt
Cost: $10 donation

One of the largest street festivals in Chicago, Do Division is a three-day music festival, food festival, and sidewalk sale that takes place at the end of May. The two music stages are curated by The Empty Bottle and Subterranean. There is also a Family Fun Fest that takes place as part of this street festival and it includes a petting zoo, mega slide, and a stage with kid’s music. Do Division has a $10 entrance fee.


When: June 2-5, 2022
Neighborhood: Lincoln Square/Ravenswood
Address: Lincoln Square, North Western Ave and West Leland Ave
Cost: Free

Maifest is a German American festival that celebrates the arrival of spring. The event features food, dancing, and live music.

Porchfest Lakeview

When: June 5, 2022, from 1 pm until 5 pm
Neighborhood: Lakeview
Address: Grace to Wolfram and Ravenswood to Racine

Residential front porches become stages for local musicians at this annual event.

Lincoln Park Greek Fest

When: June 3-5, 2022
Neighborhood: Lincoln Park
Address: 2701 N Sheffield Ave
Cost: $10 donation

A three-day summertime festival with authentic Greek food, music, and dancing hosted at St. George Greek Orthodox Church.

Chicago Gospel Music Festival

When: June 4, 2022
Neighborhood: The Loop
Address: Millenium Park

A free music festival that features some of the country’s top gospel performers. Both traditional and more unique gospel groups are included.

57th Street Art Fair

When: June 4-5, 2022
Neighborhood: Hyde Park
Address: 57th Street between Kenwood and Woodlawn
Cost: Free

The goal of this free event is to present local artists and craftspeople to the art buying public.


When: June 9, 2022
Neighborhood: Lincoln Park
Address: Cafe Brauer at the Lincoln Park Zoo

A fundraiser for the Lincoln Park Zoo that includes an open bar, bites from top Chicago restaurants, and dancing.

Fiestas Patronales Puertorriquenas

When: June 9-12, 2022
Neighborhood: Humboldt Park
Address: 2800 West Division St

A festival and carnival that takes place after the Annual Puerto Rican Day People’s Parade. The family-friendly event includes a domino tournament, a motorcycle, bar, and bicycle showcase, cultural performances, artists, an artisan market, and traditional food and drinks.


When: June 10-12, 2022
Neighborhood: Andersonville
Address: Clark Street Corridor

This summertime street festival celebrating the neighborhood’s Swedish ancestry and LGBTQ+ culture is one of the most popular things to do in Andersonville. The 2022 event will have five stages and over 50 entertainment acts plus food, drinks, and vendors selling art, crafts, and other goods. Midsommerfest takes place during Pride Month in June.

Waldo’s Forever Fest

When: June 10, 2022
Neighborhood: Andersonville
Address: Clark and Argyle Streets

This festival brings together cannabis, culture, and community and promises to be the highest celebration in Chicago. The event features live music, drag performances, local food, and immersive experiences. *It was initially scheduled for April; this is the new date.

Old Town Art Fair and the Wells Street Art Festival

When: June 11-12, 2022
Neighborhood: Old Town
Address: The Old Town Art Fair: the intersection of Wisconsin Street and Lincoln Ave
The Wells Street Art Festival: Wells Street between Division and North

It is easy to get these two festivals confused or to think that they are the same event since they take place at the same time on nearby streets in Old Town. The Art Fair is focused on art, and the Art Festival is a street festival with bands and more food and drink options.

Hyde Park Summer Fest

When: June 11-12, 2022
Neighborhood: Hyde Park
Address: Midway Plaisance (59th and Ellis Ave)

The music lineup for this fest includes Busta Rhymes, Ashanti, Lupe Fiasco, and DJ Jazzy Jeff.

Chicago Blues Festival

When: June 9-12, 2022
Neighborhood: The Loop
Address: Millenium Park
Cost: Free

The lineup of this music fest celebrates the blues genre’s past, present, and future. Over 30 bands will be performing.

Jazzin’ at the Shedd

When: Wednesdays from June 15 through August 31, 2022, 5 pm – 10 pm
Neighborhood: Museum Campus
Address: The Shedd Aquarium

The Shedd Aquarium hosts top local jazz ensembles on the terrace which offers incredible views of the city skyline and the Wednesday night fireworks. The aquarium exhibits are open during the event.

Taste of Randolph Street

When: June 17-19, 2022
Neighborhood: West Loop
Address: 900 West Randolph Street
Cost: $10 donation

Taste of Randolph Street brings local restaurants and live music together for a weekend-long street festival.

The Summer Smash Festival

When: June 17-19, 2022
Neighborhood: North Lawndale
Address: Douglass Park
Cost: $275 and up

A three-day, three stage music festival including 60+ artists and immersive art experiences. Headliners include Post Malone, Playboi Carti, Wiz Khalifa, and Young Thug.

Black Panther in Concert with the Chicago Philharmonic

When: June 18, 2022
Neighborhood: The Loop
Address: Chicago Theater

A one-night event where the Chicago Philharmonic will perform the film’s score live while the film is screened. Drummer Massamba Diop, who helped to create the score with the composer, will be joining the Philharmonic for this event.

Ravenswood on Tap

When: June 18-19, 2022
Neighborhood: Ravenswood
Address: the Ravenswood Corridor, Ravenswood and Berteau Avenues

A two-day outdoor festival celebrating the Malt Row brewing community. Attendees can taste special brews, try their hand at ax throwing, shop from local vendors, and listen to live music.

Gold Coast Art Fair

When: June 18-19, 2022
Neighborhood: The Loop
Address: Grant Park, Lake Shore Drive and Monroe
Cost: $10 per person

Shop art from 200 juried artists and see live music at this massive event.

Festival on the Square

When: June 19, 2022
Neighborhood: Bridgeport
Address: Zhou B. Arts Center
Cost: Free

Presented by the Congo Square Theater, this event is a celebration of Black art, healing, and joy that includes live music and theatrical readings.

Artists of the Wall Festival

When: June 18-19, 2022
Neighborhood: Rogers Park
Address: Loyola Park

A festival that takes place at Loyola Park on Father’s Day weekend where the 600 foot sea wall/bench is turned into 160 artists spaces and painted. Each year the wall is whitewashed and repainted by locals to fit the year’s theme (the 2022 theme is World of Tomorrow). The paintings are judged based on a few categories and all remain on display until the next year.

Millennium Park Summer Music Series

When: June 20, 2022
Neighborhood: The Loop
Address: Millennium Park
Cost: Free

Femi Kuti & The Positive Force a Nigerian Afrobeat ensemble and HAT a Moroccan born audio-visual artist will perform.


When: June 24, 2022
Neighborhood: River North
Address: Eataly

An adults-only event with unlimited Italian cuisine and drinks plus live entertainment.

Logan Square Arts Festival

When: June 24-26, 2022
Neighborhood: Logan Square
Address: Comfort Station, 2579 N Milwaukee Ave

One of Chicago’s largest summertime arts festivals, the Logan Square Arts Festival features two music stages, local artists, and food and drinks from neighborhood restaurants.

Michelada Fest

When: June 24-26, 2022
Neighborhood: Pilsen
Address: Harrison Park, 1824 South Wood St
Cost: $35 and up

Michelada Fest has 11 Michelada vendors, live music, a mechanical bull, an adult playground, and a ping pong championship.

Chicago Food Truck Summer Festival

When: June 25-26, 2022, 11 am – 7 pm
Neighborhood: South Loop
Address: 1700 Sout Wabash Street

A festival that brings together some of Chicago’s top food trucks including Lucy’s, Mexi-Tacos, Yum Dum, The Happy Lobster, The Fat Shallot, and Piko Street Kitchen.

River North LIVE!

When: June 24-26, 2022
Neighborhood: River North
Address: between the MART and the Chicago River, 222 Merchandise Mart Plaza
Cost: $10 (can be purchased online)

It seems that the Taste of River North has morphed into a new riverfront music festival featuring bands including The Calling, EMO Night Brooklyn, and Baysik plus food and drinks from Fogo de Chao.

Dragon Boat Race for Literacy

When: June 25, 2022
Neighborhood: Chinatown
Address: Ping Tom Memorial Park

Each June dragon boat races are held at Ping Tom Memorial Park to promote Asian culture while helping to raise money for neighborhood literacy programs. At this race, 32 teams each consisting of 18 paddlers, 1 drummer, and 1 flag catcher compete in beautifully decorated dragon boats.

Millennium Park Summer Music Series

When: June 30, 2022
Neighborhood: The Loop
Address: Millennium Park
Cost: Free

Singer-songwriter Abigail Washburn and Choctaw singer Samantha Crain will perform.


When: June 30, 2022, from 5 pm – 10 pm
Neighborhood: The Loop
Address: LaSalle and Quincy and along the LaSalle Corridor

A one-night street festival that celebrates art, music, and performance and that brings life to unexpected parts of The Loop.

Chicago Cocktail Social

When: June 30, 2022, at 6:30 pm
Neighborhood: River West
Address: Galleria Marchetti, 825 West Erie
Cost: $45- $70

This event features some of Chicago’s top bartenders along with gourmet food, and music from Cage + Aquarium. This year’s lineup includes bartenders from Big Kids, Proxi, Tack Room, Sportsman’s Club, Drifter, Scofflaw, Moneygun, and Lazy Bird.

Chicago Pride Events:

Shedd Aquarium Pride Night

When: June 1, 2022, 6 pm – 10 pm
Neighborhood: Museum Campus
Address: Shedd Aquarium
Cost: $14.95 – $39.95

An event in partnership with A Queer Pride with multiple DJs and an ocean-themed drag showcase. * This is a 21+ event.

Pride Fest

When: June 18-19, 2022
Neighborhood: Boystown / Northalsted
Address: Halsted Street between Addison and Grace
Cost: $15 suggested donation

Pride Fest takes place the weekend before the Pride Parade. The event brings together three stages of live music and performances, food and drink, drag shows, and over 100 art and crafts vendors.

Drag Me to the Fairmont

When: June 18, 2022, 7:15 pm
Neighborhood: Streeterville
Address: Fairmont Chicago, 200 North Columbus Drive
Cost: $45 and up

In partnership with the Aids Foundation, Fairmont Chicago will host a ‘Drag Me to the Fairmont’ drag show featuring live thrilling performances headlined by Lady Bunny and Miz Cracker.

Lincoln Park Zoo’s Adults Night Out: Pride Party

When: June 23, 2022, 6:30 pm – 10 pm
Neighborhood: Lincoln Park
Address: Lincoln Park Zoo

In addition to providing the opportunity to explore the zoo in a calmer kid-free environment, this event includes Drag Queen BINGO, a DJ, lawn games, and a cash bar.

Pride North Festival

When: June 24-26, 2022
Neighborhood: Rogers Park
Address: off the Morse Red Line – Glenwood Avenue Arts Corridor

A block party with two entertainment stages, three dance floors, food, and drinks. It’s considered to be the Pride Parade After Party.

Pride in the Park

When: June 25-26, 2022
Neighborhood: The Loop
Address: Grant Park
Cost: Purchase tickets online in advance, GA tickets start at $45

An outdoor music festival highlighting LGBTQ+ performers, artists, and vendors. Headliners include The Chainsmokers and Alesso.

Pride at Navy Pier

When: June 25, 2022, 12pm – 11:30 pm
Neighborhood: Streeterville
Address: Navy Pier
Cost: Free

A full-day event with storytelling, live music, educational programs, and performances that celebrate diversity and the LGBTQ+ community.

Pride Parade

When: June 26, 2022 at noon
Neighborhood: Boystown / Northalsted
Address: Broadway and Halsted Streets – MAP

The Pride Parade marches through parts of Uptown, Lakeview/Boystown, and Lincoln Park. It is a massive event that draws a crowd of thousands.

Chicago Urban Pride Festival / Gay Pride Day Picnic

When: June 26, 2022, 12 pm – 8 pm
Neighborhood: Hyde Park
Address: Jackson Park
Cost: Free

A free family-friendly pride event featuring 6 DJs, entertainment, dance performances, and drag shows. A ticketed after-party is hosted at The Promontory on June 26. This is the South Side’s largest pride event.