June is the officially here and that means a month full of free events, unique things to do, and interesting places to seek all summer long. This month, seek beyond your neighborhood by attending a festival on the Southwest side of the city in Little Village, seeing a Movie in the Park on another side of town, or volunteering with Chicago Cares during their annual Serve-a-thon event. Kick off summertime Chi by checking out the latest guide on things to do all month long in Chicago.
Wednesday | June 27th | 5:30 p.m.
wework | 111 W Illinois St. |$25 – $38
Fashion Group International invites you to learn more about the impact of technology on today’s ever-changing fashion industry. Learn how local businesses and entrepreneurs are pushing the way they develop products and reach consumers through new and emerging technology. For more details on this event, visit the event page
Randolph Street Market: Red, White, & Cool
Saturday – Sunday | June 23rd – 24th | 10:00 a.m. – 5:00 p.m.
Randolph Street Market | 1341 W Randolph St. | $0 – $10
Randolph Street Market Festival continues their outdoor and indoor summer market this month featuring 300 vendors with the best vintage, antique, & repurposed furniture, art, decor, ephemera, vintage fashion for men/women, fancy foods, global goods and much more. The family-friendly market not only features a plethora of vendors, but market bars, cabanas, and shade shack for lounging and listening to a live band every day. To learn more about this month’s Randolph Street Market, be sure to visit their website here.
Opening Reception: Fashion, Body, and Garment
Friday | June 1st | 6:00 p.m. – 10:30 p.m.
Bucktown Gallery | 2207 N. Western Ave. | Free
This month, join over a dozen artist as they explore the inescapable force and industry of fashion, body, and garment. A group show featuring work by hand-selected artists who bridge the gap between the art and fashion realms while posing relevant questions that engage in the ever-evolving dialogue emerging from the two industries. To learn more about the opening reception and show duration, visit the event page here.
Do Chicago Fashion Fest
Friday – Sunday | June 4th – 6th | Time Varies
Division & Damen St. | $5 Donation
Do Fashion at Do Division Street Fest kicks off the first weekend of June with three nights of runway fashion shows for kids, dogs, and adults. There will be over a dozen vendors, designers, makers, and creators showcasing their work during the weekend. The fashion fest will also feature onstage demos, boutique vendors, fashion photo walls, sidewalk sales, and pop-up shops. For more information on the vendors and the full schedule of fashion events during Do Division, be sure to visit the event page.
Taste of Randolph Street
Friday – Sunday | June 15th – 17th | Time Varies
Randolph and Peoria | $10 Donation
Taste of Randolph commemorates its iconic street festival with a 22nd Anniversary celebration by bringing together the biggest and brightest names in Chicago dining, featuring over 16 unique restaurants. In addition to the delectable food, some of the nation’s hottest up-and-coming bands and musicians, as well as the biggest names in Chicago house music, performing on two stages and a DJ stage, to entertain guests on their culinary adventure. For a full list of participating restaurants, musical acts, and performances, as well as VIP tickets, be sure to visit the event website here.
Pilsen Food Truck Social
Saturday – Sunday | June 9th – 10th | 11:00 a.m. – 9:00 p.m.
18th Street between Racine and Throop | $5 Optional Donation
Pilsen Food Truck Social (one of my favorite festivals) rolls out this month in the eclectic Southwest community of Pilsen. The historic neighborhood will host the annual festival featuring over 25 food trucks and local restaurants alongside art and music reflecting the rich and vibrant culture of the neighborhood. With a huge selection of food options, it will hard to choose just one. Fest-goers will have an option to try six sample-sized portions from any participating food truck or restaurant on site. Be sure to check out one of the city’s most well-attended festivals this month. For a full list of participating vendors and restaurants, visit the website here.
Puerto Rican Festival & Parade
Thursday – Sunday | June 14th – 17th | Time Varies
Humboldt Park | Division and Western | Free
The Puerto Rican Festival & Parade, or Fiestas Puertorriqueñas, is one of the most significant Latin events in the nation and brings four days of fun, food, and festivities to Chicago, Illinois. With live music, authentic Caribbean cuisine, arts and crafts, carnival rides and more, the festival offers something for everyone to enjoy. This year, the Puerto Rican People’s Parade will return to the traditional ( and original) parade site in downtown Chicago. For more information and schedule of events, be sure to visit the website here.
Chicago Japanese Matsuri
Saturday – Sunday | June 23rd – 24th | Time Varies
New City | 1457 N Halsted St. | Free
Take a trip to Japan this summer without leaving the city. The Chicago Japanese Matsuri hosted by Kizuki Ramen & Izakaya and Japanese Culture Center – 日本文化会館 will host a traditional Japanese summer festival in the heart of Chicago this summer. Guests are invited to experience authentic Japanese festival foods, cultural performances of Taiko drumming, Shodo/large scale calligraphy, Traditional Martial Arts, Sumi-e ink painting, Cosplay Contests and so much more. All festival foods will be prepared by chef Kevin Yu and his team from Kizuki Ramen & Izakaya which means true Japanese culinary authenticity and deliciousness! The festival foods will include Takoyaki, Chicken Karaage, Potato Croquette, Okonomiyaki and many other classic authentic Japanese dishes. For more event details, be sure to visit the festival event page.
Saturday | June 16th | 8:00 p.m.
The Geraghty | 2520 S Hoyne Ave. | $150
The 3rd Annual Agora Sneakerball is a charitable fundraising gala converging fashion, art, music, and philanthropy into one purposeful evening. Kicks 4 the City is a service-oriented group that is committed to providing shoes to those experiencing homelessness nationwide. Last year, the powerful gala provided an evening of entertainment and awareness to over 600 culturally diverse guests. The Sneakerball is an invite-only event, request your ticket by visiting Agora Snearkball.org.
Chicago Dragon Boat Race For Literacy
Saturday | June 23rd | 8:00 a.m. to 5:00 p.m.
Ping Tom Memorial Park | 300 West 19th St. | Free
The Chicago Chinatown Chamber of Commerce will host its 18th Annual Dragon Boat Race for Literacy Ping Tom Memorial Park in Chinatown. The Chinese dragon boat race dates back to over 2,000 years and is a favorite sport among Chinese and Asian communities all over the world. Thirty-two dragon boat race teams will compete on the south branch of the Chicago River in beautifully decorated dragon boats, each consisting of up to 20 members: 18 paddlers, one drummer, and one flag catcher. Over 10,000 visitors are expected to attend this annual event. This event for all ages that supports local school and organizations. To participate or to learn more, be sure to visit the website here.
Saturday | June 23rd | Time Varies
Location Varies | $0 – $15
Serve-a-thon is Chicago’s most significant day of volunteering. The service event is known to draw over 5,000 volunteers who will make an impact at upwards of 30 locations across Chicago. The most significant day of service will breather new life into Chicago Public Schools, shelters, and other not-for-profit organizations. To register for this event and to volunteer for opportunities all year long, be sure to check out the Chicago Cares.org.
Arts + Culture:
SHADE: An Actually Diverse Comedy Show
Friday – Saturday | June 15th – 16th | 8:00 p.m.
Steppenwolf Theatre| 1650 N Halsted St. | $20
Laugh it up with Chicago’s best LGBTQIAP comics during Pride Weekend this month in Chicago. SHADE: An ACTUALLY Diverse Comedy Show features comedians from marginalized communities–people of color, LGBTQIAP, and women–and presents shows around a particular theme. All are welcome; Shade is mandatory. The event is a part of Look Out, a series of emerging artists and performance legends who are familiar and new faces of Steppenwolf. To register for SHADE, make your way to event website by following the link here.
Black Owned Chicago Trolley Tours
Tuesdays | June | Time Varies
Location Varies | $20 – $30
Black Owned Chicago, a black-owned and operated directory to black-owned and operated businesses in Chicago will host a series of trolley tours throughout June. “The Black Owned Chicago Trolley Tours” that will highlight Black monuments and Black-owned businesses in the city of Chicago. Highlights will include Eden Place Nature Center (the only Black-owned and operated farm & nature center in Chicago), DuSable Museum of African American History, President Barack Obama’s Hyde Park home, and more. Guests will also leave with a “goodie bag” of samples from Black-owned businesses in Chicago, i.e., coffee, popcorn, etc. To purchase your tickets for this event and learn more about Black Owned Chicago, be sure to visit their website here.
Movies in the Park
Monday – Sunday | June 1st – 30th | Time Varies
Location Varies | Free
Movies in the Parks is part of Night Out in the Parks, which features more than 2,000 cultural & arts events in parks throughout the city each year. Hollywood stars return to Chicago skies this summer, as Movies in the Parks brings big-screen entertainment to local parks for the eighteenth season. Featuring everything from classics from the Golden Age of Hollywood and retro childhood favorites to the best family-friendly box office favorites from recent years. Check out the full lineup by visit the Chicago Park District website.
Chicago Immigrant Stories
Thursday | June 14th | 6:30 p.m. – 8:00 p.m.
Millennium Park |201 E Randolph St. | Free
This month, experience the world premiere performance of Orbert Davis and Howard Levy’s composition, based on a series of collaborations with musicians from Chicago’s Chinese, West African, and South Asian / Indian immigrant communities. This event is held at Millennium Park and hosted by the Chicago Jazz Philharmonic. Head over the event page for more information on this event.