June 27th – 30th in Chicago: Chicago is a Drag, Summer Smash and More Things To Do this Weekend

This weekend in Chicago, shop a fabulous collection of Midwest style offerings at the Skyline Event Series at the Roosevelt Collection Shops. Go berry picking at Bloomingdale Trail. Join the LGBTQ community for a celebration of Pride at the Annual Chicago Pride Parade. Turn up to some of the new and emerging hip-hop artists in Douglas Park at the Lyrical Lemonade Summer Smash. Check out these events and more fun things to do in Chicago this weekend.


Skyline Event Series: Rooftop Vintage Market

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

Roosevelt Collection Shops |150 W Roosevelt Rd. | Free

Rooftop Vintage Market as feature on The Haute Seeker in July 27th - 30th 2019 events in Chicago
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 with these cool local Chicago stores at this weekend-long event. For a list of vendors and more details on this Chicago market in the South Loop, visit the event page here.

Randolph Street Market Chicago: Red, White, and Cool

Saturday – Sunday | June 29th – 30th | 10:00 a.m. – 5:00 p.m.

Randolph Street Market | 1341 W Randolph St. | $0 – $50

Randolph Street market as featured on The Haute Seeker in July 27th - 30th 2019 events in Chicago
Image | Randolph Street Market

Find unique good from 200 vendors at Randolph Street Market this weekend in the West Loop. Randolph Street Market, the outdoor/indoor Chicago based market will host its June event, featuring vintage, antique, and repurposed furniture as well as art, decor, fashion, global cuisine and more. Make a fun day of shopping in the heart of the West Loop at this month’s Randolph Street Market. To purchase tickets, visit the website here.

Food + Drink: 

2019 Woodlawn 5K Dash and Food Truck Fest

Saturday | June 29th | 8:00 a.m. – 3:00 p.m.

Midway Plaisance |1130 Midway Plaisance | Free

2019 Woodlawn Food Truck Festival as featured on The Haute Seeker in July 27th - 30th 2019 events in Chicago
Image | Woodlawn Diversity in Action

The Woodlawn 5k Dash and the Woodlawn Food Truck Fest will take place together to highlight mental health and wellness and youth violence prevention. Both events aspire to bring the community together through food, wellness, and growth of the Woodlawn neighborhood. For more details on this event, visit the website.

Berries for the Bloomingdale Trail: “The Picking”

Thursday | June 27th | 6:00 p.m. – 7:30 p.m.

Bloomingdale Trail | 1600 – 3700 W Bloomingdale | Free

Berries for Bloomingdale as featured on The Haute Seeker in July 27th - 30th 2019 events in Chicago
Image | Bloomingdale Trail

Join the Friends of the Bloomingdale Trail on Thursday, June 27th for an evening of berry picking. Every June the Serviceberry ripens over the Bloomingdale Trail and across Chicago. Part one of the event includes group picking as well as a short talk on native fruits and Indigenous food systems and practices with Fawn Pochel (First Nations Oji-Cree), Education Director of the American Indian Center. Find more details on this food and educationally focused event as well as part two of this summer series by visiting the Facebook page here.


Chicago Pride Parade

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

Montrose Avenue and Broadway | Free

Chicago Pride Parade image by Second City Outlaws as feature on The Haute Seeker in July 27th - 30th 2019 events in Chicago
Image | Second City Outlaws

Celebrate the epic closure to Pride Month with the LGBTQ celebration during the 2019 Chicago Annual Pride Parade. This year’s parade centers are the theme of “Stonewall 50: Millions of Moments of Pride.” The festival kicks off at Montrose Avenue and Broadway in the Uptown neighborhood and ends at the intersection of Diversey Parkway and Sheridan Road in Lincoln Park. This festival welcomes and celebrates family and friends of all ages and diverse backgrounds. For more details on the parade, visit the website.

Arts + Culture:

Chicago is a Drag Festival

Friday | June 28th | 4:00 p.m.

Cheetah Gym Parking Lot |5238 N Clark St. |$25

Chicago is a Drag Festival as featured on The Haute Seeker in July 27th - 30th 2019 events in Chicago
Image | A Queer Pride

Closeout the celebration of Pride month in Chicago with Chicago Is A Drag Festival. Chicago Is A Drag Festival (CIADF) is the first ever outdoor street festival of its kind that showcases Chicago’s drag culture. Curated by A Queer Pride, the lineup of CIADF will host performances from 50 of Chicago’s top kings, queens and club kids who represent and celebrate the past, present and future of Chicago drag. Headliners for the festival include Raja, Candis Cayne, Spikey Van Dykey and is hosted by special guests Tiffany “New York” Pollard and TS Madison. To purchase tickets, visit the website here.

The Lyrical Lemonade Summer Smash

Saturday – Sunday | June 29th – 30th | Time Varies

Douglas Park Chicago | 1401 S Sacramento Dr. | $159

The Lyrical Lemonade Summer Smash as featured on The Haute Seeker in July 27th - 30th 2019 events in Chicago
Image | SPKRBX

Turn up to some of the best local and world-renowned hip-hop artists this weekend in Chicago. Summer Smash features two days of premier hip-hop music in the Midwest. 50 + artists will be performing radio and underground music across 3 stages. From Chicago born rapper Juice Wrld to artists featured on the 2019 XXL Freshman Class cover, this is young and fresh hip-hop concert that is sure to be a smash. To purchase tickets, visit the website here.

Need more things to do this week—I got you! Check out the June 2019 Guide for more events taking place in Chicago June 27th – 30th.

What I’m Seeking:

This weekend is definitely going to be a busy one for me. Thursday, I will be kicking off my weekend with the grand opening of  Play Kitchen & Cocktails, a new bar and restaurant in the Gold Coast. Friday, is very much up in the air. Saturday, I will be volunteering at the Art Insitute(cool off and come visit me) as well attending the Silver Room Block Party. Sunday, I hope to hit up a festival that I have never been too, and wine down my week with a little self-care. As always, follow me @The Haute Seeker on Instagram to seek what I am seeking in Chicago. Oh, and stay hydrated out there!

Seek the Unseen in Chicago

Subscribe today and get on The Haute List! The go-to newsletter for unique happenings in the city of Chicago.

Share your thoughts! I would love to hear from you.

This site uses Akismet to reduce spam. Learn how your comment data is processed.