Eastern view of Navy Pier in Chicago

Guide to Chicago June Events 2019

While May brought a ton of showers June weather is makes for long hours of summer fun in the city. This guide to June events in Chicago features a month of things to do including major food truck festivals, late-night artisan markets, South Side bike tours, major exhibition openings, and more.


Allstars of Project Runway

Saturday | June 29th | 5:00 p.m.

Theater on the Lake | 2401 N Lake Shore Dr. | $350 – $500

Allstars of Project Runway feature in The Haute Seeker Chicago June Events Guide 2019
Image | Journey Care

Enjoy a luxury fashion show featuring Project Runway Allstars in Chicago. Five designers from the hit show ‘Project Runway’ will create exclusive fashions. The event that is the first of its kind will help spotlight care for children and adults with serious illnesses through fashion. The fashion show, taking place on Saturday, June 29th, will include tickets to the show, food, beverages, and a live auction. To purchase your tickets to the couture for a cause event, visit the website here.

Skyline Event Series: Rooftop Vintage Market

Friday – Saturday | June 28th- 29th | Time Varies

Roosevelt Collection Shops |150 W Roosevelt Rd. | Free

Rooftop Vintage Market feature in The Haute Seeker Chicago June Events Guide 2019
Image | Roosevelt Collection Shops

Find a fabulous selection of Midwest style offerings this June at the Roosevelt Collection Shops. The “Skyline Event Series” in partnership with Twisted Vintage Decor features handmade goods and handpicked vintage items from small businesses located throughout the Chicagoland area. Choose between an evening or day market at this weekend-long event. For a list of vendors and more details on this Chicago market, visit the event page here.

Sauced Spring Night Market

Thursday | June 20th| 6:00 p.m. – 11:00 p.m.

House of Vans | 113 N Elizabeth St. | Free

SAUCED Night Market at House of Vans feature in The Haute Seeker Chicago June Events Guide 2019
Image | SAUCED

Head to the House of Vans this month for the spring addition of SAUCED Night Market. The late night shopping event features over 50 local retailers, food makers, artisans, and vendors. In addition to the unique shopping, guests will also be surrounded by live art, music, and surprises only a SAUCED market could bring. Stay tuned on the full release of participating vendors and more details by visiting the website.

Pop of Culture

Saturday | June 29th | 12:00 – 6:00 p.m.

2557 W North Ave. | Free

Pop of Culture feature in The Haute Seeker Chicago June Events Guide 2019
Image | Pop of Culture

Pop of Culture is a unique traveling shopping experience featuring the best local and international brands. The event will take place in Humboldt Park and feature handmade accessories, contemporary clothing, African clothing, sandals, jewelry, natural hair/skin products, and more. Get more details on this culturally focused shopping event by visiting the Pop of Culture Popup on Instagram.

Food + Drink:

Vegandale Fest Chicago

Saturday | June 22nd | 11:00 a.m. – 7:00 p.m.

Grant Park | 100 S Lake Shore Dr. | $10

Vegandale Fest featured The Haute Seeker Chicago June Events Guide 2019

Embrace the vegan lifestyle in Chicago this summer at Vegandales Fest in Chicago. Based in Toronto, Vegandale is a mecca for the ethically minded and hungry, with the best of vegan food, goods, and services co-existing on one city block. Vegandale shares its message with Chicago this month. It features over 100 of the best vendors from across North America will be available for one day only, dishing up incredible vegan food, drinks, and merchandise. The festival will also feature great music, stage entertainment, larger than life art installations and more. Tickets and a list of participating vendors are available on the website.

Chicago Taco & Tequila Fest

Saturday | June 15th | 11:00 a.m. – 9:00 p.m.

2491 N Cannon Dr. | $10 – $40

Chicago Taco and Tequila Fest featured The Haute Seeker Chicago June Events Guide 2019
Image |  Special Events Management

Tacos and Tequila Fest brings a sampling of good food and tasty cocktails together this month in Chicago. The festival features traditional and exotic in ingredient-stuffed tortillas paired with tequila-infused cocktails. Plus, margarita flights, tasting, along with living bands and other entertainment. This event is 21+. Tickets range from $10 – $40 and include one complimentary margarita. For more information, visit the event page. Find a deal on tickets by following this link.

Chicago Food Truck Festival

Saturday – Sunday | June 22nd – 23rd | 10:00 a.m. – 7:00 p.m.

1800 S Wabash Ave. | Free

Chicago Food Truck Festival featured The Haute Seeker Chicago June Events Guide 2019
Image | Chicago Food Truck Festival

The Chicago Food Truck Festival takes places this month on Wabash Avenue on the South Side of Chicago. The festival features gourmet food trucks from over 45+ major vendors. In addition to the food trucks, there will also be nonstop entertainment and of course, refreshing drink options. Entry to the food festival is free. But, if you want to skip the link, update to VIP which includes early admission and two drink tickets. To purchase tickets and a full lineup of food trucks, visit the event page.

Ravenswood On Tap

Saturday | June 22nd – 23rd | Time Varies

Ravenswood and Berteau| $5 – $35

Ravenswood on Tap 2019 feature in The Haute Seeker Chicago June Events Guide 2019
Image | Greater Ravenswood Chamber of Commerce

Ravenswood On Tap is a two-day craft beer festival featuring beer and spirits from local breweries from the Ravenswood neighborhood in Chicago. Lovingly known as “Malt Row”, the annual fest features craft beverages, food from some of Chicago’s favorite restaurants and food trucks, a well-known lineup of live music, and handmade goods from local retailers and artists. For more information on this crafty event—visit the website here.


Chicago Pride Parade

Sunday | June 30th | 12:00 p.m.

Montrose Avenue and Broadway | Free

Chicago Pride Parade image by Second City Outlaws feature in The Haute Seeker Chicago June Events Guide 2019
Image | Second City Outlaws

Pride Month in June is a celebration of Chicago’s vibrant LGBT community. Every year, on the last Sunday of June, the Chicago Pride Parade concludes the energetic month in the Boystown neighborhood of the city. This year’s parade centers are the theme of “Stonewall 50: Millions of Moments of Pride.” This festival welcomes and celebrates family and friends of all ages and diverse backgrounds. For more Pride focused events and details, visit the website here.

Monarch Art and Wellness Fair

Saturday – Sunday | June 22nd – 23rd | Time Varies

Hyde Park Art Center | 5020 S Cornell Dr. | Free

Monarch at the Hyde Park Art Center feature in The Haute Seeker Chicago June Events Guide 2019
Image | Hyde Park Art Center

The Hyde Park Art Center, in addition to its commitment to local art, will become a wellness center this month. The Monarch Art and Wellness annual fair is the first of its kind. The skill and wellness experience will celebrate women, femme, and gender non-binary artists, healers, and small businesses in Chicago. The fair presents over 30 local vendors and offers an active roster of public programs on physical, mental, spiritual, and sexual wellness resources that are available throughout the city. Learn more about the fair that is free and open to all ages by visit the event page here.

Roll N Peace

Friday | June 14th | 6:00 p.m.

Englewood Square Parking Lot | 63rd and Halsted St. | Free

Roll N Peace flyer feature in The Haute Seeker
Image | Think Outside Da Block

Join the residents of Englewood this month for an evening bike tour through the historical community. “Roll N Peace” is a critical mass bike tour that will guide participants on a journey of the transformative South Side community as well as a visit through historical landmarks and places of interest. Participants are encouraged to BYOB(bring their own bikes) or rent them for free. For more details on this neighborhood bike tour, visit the Facebook page here.

Arts + Culture:

Virgil Abloh: “Figures of Speech

Sunday – Saturday | June 10th – September 22nd | Time Varies

Museum of Contemporary Art | 220 E Chicago Ave. | $15

Virgil Abloh by Katrina Wittkamp feature in The Haute Seeker Chicago June Events Guide 2019
Virgil Abloh | Photo by Katrina Wittkamp

Virgil Abloh: “Figures of Speech” is one of the most highly anticipated June events and exhibitions set to open in Chicago. The first-ever museum exhibition is devoted to the work of the ultramodern, genre-bending artist and designer Virgil Abloh, who is from Rockford, Illinois. The exhibition covers seven areas of Virgil Abloh’s work over the past twenty years, chronicling the different pillars of his work in fashion, music, art, furniture, and graphic design. In addition to the exhibition will be public art projects around Chicago, a specially curated concept and design store, youth-led events, and other related programs. For more details on the Virgil Abloh and “Figures of Speech” exhibition, visit the MCA Chicago.org.

Andersonville Midsommarfest

Friday – Sunday | June 7th – 9th | Time Varies

Clark Street between Foster and Catalpa| $10 Donation

Andersonville Midsommarfest flyer in The Haute Seeker
Image | Midsommarfest

Midsommarfest takes places during the 2nd weekend in June. The festival celebrates the old-world Swedish traditions of the Andersonville neighborhood. The three-day festival is full of music, dancing, kids entertainment, and tasty international food. See why this is one of the best June events to attend this summer. For more details on this festival, visit the website.

ACTIVATE: Premiere in Chicago

Thursday | June 6th| 5:00 p.m.

MacChesney Court | E. Lake St. and N. Garland Ct. | Free

People enjoying ACTIVATE in Chicago

Extend your time in the Loop this summer with ACTIVATE. The popular annual series of pop-up arts programs takes place around the downtown neighborhood known as The Loop and transforms ordinary spaces in unexpected creative exhibition spaces. Experience a public art offering this summer curated by local creatives in Chicago. This month’s ACTIVATE takes place at MacChesney Court and features a dozen different artistic elements from some of Chicago’s best artists. ACTIVATE is a great activity to checkout during a summer weeknight in the city. Don’t forget to RSVP for a free drink ticket as well!

Printers Row Lit Fest

Friday – Sunday | June 8th – 9th | 12:00 p.m. – 9:00 p.m.

W. 18th St. and Paulina | Free

Printers Row Lit Fest feature in The Haute Seeker Chicago June Events Guide 2019
Image | Printers Row Lit Fest

One of the most prominent Chicago June Events is the Printers Row Lit Fest. Featured in the Chicago summer festivals 2019 guide, the Printers Row Lit Fest is a literary festival that attracts thousands of visitors each year. Now in its 35th year, the event is back and bigger than ever—providing guests opportunities to meet new authors, grab interesting books, and enjoy more literary activities that you will not find anywhere else this summer. For details on this event, visit the website here.


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