11 Things to Do in Chicago This June

June is the dawn of summer, and summer in Chicago is when we all come out to play. If you’re ready to ditch the indoors and hit the streets to make the most out of this month, make sure to head to these top events.

Taste of Mexico

june events chicago
Photo Credit: Special Events Management

May 31 – June 2 @ Little Village


This annual neighborhood celebration highlights the vibrant Mexican community in Chicago with cultural flavors, live music, carnival rides, and arts and crafts from 3pm – 10pm on Friday and from 12pm – 10pm on Saturday and Sunday.

Do Division Street Fest

june events chicago
Photo Credit: Do Division Street Fest

May 31 – June 2 @ West Town


Spanning 10 city blocks and featuring live music, delicious food and drink vendors, and local retailers, this is arguably the most popular outdoor street festival in the city. The festival asks for a $10 donation.

Chicago Ale Fest

Chicago Ale Fest


June 1 @ Grant Park

Chicago Ale Fest returns for its summer edition to Butler Field in Grant Park, serving more than 200 American craft beers, also featuring live music and food trucks. General admission starts at $49, and we already found you a top-notch parking spot.


Run for the Zoo

june events chicago
Photo Credit: Todd Rosenberg for Lincoln Park Zoo

June 2 @ Lincoln Park Zoo

The 41st annual race that helps keep Lincoln Park Zoo admission free returns with 5k and 10k race options, a kids’ obstacle course, themed shirts, and an after-party at the zoo. The race sells out fast, so register now! Prices start at $25 for kids and $39 for adults.


Chicago Blues Festival

june events chicago

June 7 – 9 @ Millennium Park


The world’s largest free blues festival returns with local, national, and international artists performing for a weekend at Millennium Park. Admission is free.

World Naked Bike Ride

june events chicago
Photo Credit: Chicago Naked Ride

June 8 @ TBD


Strip down to your skivvies and traverse the streets of Chicago with a group of other nude bicyclists for a liberating nighttime event. The secret meeting location is disclosed in the days leading up to the event.

Pilsen Food Truck Social

june events chicago
Photo Credit: Pilsen Food Truck Social

June 8 – 9 @ Pilsen

Head to 18th and Allport to feast on mobile eats, sip Revolution beers, and listen to local music on an outdoor stage. A $20 sampler tickets gets you six food truck samples. Food truck lineup is TBD.

Taste of Randolph

Taste of Randolph
Photo Credit: Taste of Randolph

June 14 – 16 @ West Loop

The 23rd anniversary of this highly-attended festival on Restaurant Row returns with eats from over 16 restaurants, along with music by up-and-coming artists. The community suggests a $10 donation.


may events chicago
Photo Credit: Youtube

June 15 @ Hollywood Casino Ampitheatre

Rock out at this one-day music festival at the Hollywood Casino Amphitheatre presented by Chicago’s WKQX, featuring bands like The Lumineers, Young the Giant, Blue October, AJR, Catfish and the Bottleman, and more. Presale tickets are going for $20.

Country LakeShake

june events chicago
Photo Credit: Country LakeShake

June 21 – 23 @ Northerly Island

Chicago’s premier country music festival on the lake reprises at Northerly Island, with Miranda Lambert, Keith Urban, and  Maren Morris headlining this year. Prices start at $80.00.

Chicago Pride Fest

Chicago Pride
Photo Credit: ChicagoPride.com Facebook

June 22 – 23 @ Boystown

The annual two-day parade and street festival in Boystown celebrates the accomplishments of the LGBT community with live performances, a Pride Pageant, and more.

Chicago Pride Parade

june events chicago
Photo Credit: Chicago Pride

June 30 @ Broadway & Montrose

Get your Pride on at the 50th anniversary of Chicago’s iconic LGBTQ+ celebratory parade.


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