It’s finally May. One of my favorite months of the year. May, especially after Memorial Day, is the official kick-off to everything summer in Chicago. From neighborhood festivals to outdoor markets, to Mother’s Day activities and intricate art events––this is what the month of May in Chicago is all about. Check out the guide to May 2019 events in Chicago and make your May that much more memorable.
RETROSPECT Vintage Modern Fashion Market
Thursday – Sunday | May 2nd – 5th | Time Varies
2260 S Grove St. |$12 – $35
Shop handpicked vintage finds from 50 fabulous dealers from around the U.S and Europe at RETROSPECT Vintage Modern Fashion Market in Chicago Thursday, May 2nd through the 5th. The market will feature the most gorgeous, beautifully preserved clothing for women, men, and children as well as a variety of accessories, jewelry, shoes, textiles, and more from the 1890s to 1990s. Pioneered by Sally Schwartz, RETROSPECT caters to local collectors and vintage fashion enthusiasts. Festivities surrounding the event include shopping, films, and an on-site cafe, informal modeling, and more! To purchase tickets to the event, visit the RETROSPECTchicago.com.
Saturday – Sunday | May 11th – 12th | 11:00 a.m. – 6:00 p.m.
S. Halsted St. between W. 18th St. & S. Canalport Ave.| Free
Join Renegade Craft for their annual May market. The al fresco Mother’s Day marketplace in Pilsen’s Chicago Arts District places over 180 local and national Makers and Designers together. The perfect shopping experience to enjoy with your moms, daughters, sisters, and role models. For a list of participating vendors, visit the website here.
Sunday | May 19th | 10:00 a.m.
Revel Fulton Market | 1215 West Fulton Market | $0 – $15
Covet Market is a boutique-sized makers’ market sparking conversation about creativity in Chicago. Join for a day of creative conversation, shopping, sampling, learning, eating and socializing in the vibrant West Loop neighborhood. Stop in or stay a while taking in the variety of vendors, artists, purveyors, speakers, and activities. Grab some friends and make a day of it at Revel Fulton Market. Follow the link for special admission.
Lost & Found- Resale Popup
Sunday | May 12th | 3:-00 – 8:00 p.m.
Emporium Wicker Park | 1366 N Milwaukee Ave. | Free
Find unique items to fit all attitudes and lifestyles at LOST & FOUND- Resale Pop-up in Wicker Park this month. The curated resale event caters to those of the underground. From Alternative, Punk, Drag, Goth, Disco, Metal, Queer, and Vintage––thrift and hang out while listening to eclectic tunes while shopping goods at this unique event. For more details, visit the Facebook page here.
Food + Drink:
Chicago Sake & Japanese Spirit Fest
Saturday | May 11th | 2:00 p.m. – 5:00 p.m.
Katana | 339 N Dearborn St. | $25 – $35
Taste over 20 varieties of Sake as well as a small variety of Japanese Spirits & Beers at this month’s Chicago Sake and Japanse Spirit Fest. The event will also offer small bites from Katana’s Award Winning Chef’s. General admission to the event includes a 3-hour tasting. For tickets to the event, visit ChicagoSakeFestival.com. Don’t forget to enter the promo code “PARTY” for discounted tickets!
Chicago Beer Classic
Saturday | May 4th | 11 a.m. – 7:30 p.m.
Solider Field | 1410 Museum Campus Dr| $69 – $89
Nothing says summer like a cool, crisp, beer—or hundreds of them. Chicago Beer Classic celebrates unique beers on the grass of iconic Soldier Field. Enjoy samples and learn from a lineup of breweries while discovering new favorites alongside fellow beer enthusiasts at Chicago’s only beer fest on the grass of Soldier Field. To purchase tickets to the event, visit Chicagobeerclassic.com.
Joy District and Hubbard Inn Combined Derby Day Party
Saturday | May 4th | 3:00 p.m.
Hubbard Inn and Joy District |110 and 112 W. Hubbard St| $10
Derby Day in Chicago just more festive! Join Joy District and Hubbard Inn for double derby enjoyment at their first event combined day party in River North. The sister restaurant will both broadcast the race and offer food and drink specials such as 9 Mint Juleps. Light appetizers from Executive Chef Jason Hedin, live music, and entry prizes will also be available. Guests are encouraged to dress in their best derby attire as there will be contests for best seersucker suit and best hat for a cash prize. To purchase tickets, visit the event page here. Reservations are also available via email at firstname.lastname@example.org.
Food Truck Social Presented by Metro by T-Mobile
Saturday | May 11th | 7:30 p.m. – 10:00 p.m.
Lincoln Park Zoo | 2200 N Cannon Dr. | Free
Where can you enjoy grilled cheese, doughnuts, pierogis, tacos, and more—all in one place? At Food Truck Social at Lincoln Park Zoo Presented by Metro by T-Mobile, of course! Experience the finest meals (on wheels) Chicago has to offer, while also enjoying the zoo after hours. In addition to dozens of food trucks, there will be fun activities, live music, and drinks available for purchase. This event is perfect for the entire family to enjoy. Tickets are $10 and do not include food with entry. To purchase tickets to the event, visit the website here.
Embarc’s 9th Annual Variety Spectacular Chicago Showcase 2019
Thursday | May 16th | 6:30 p.m. – 11:00 p.m.
Moonlight Studios | 1446 W Kenzie St. | $100 – $1000
Artists, musicians, chefs, and creatives of all kinds will showcase their talents in the distinctive and vibrant style that makes our city great. With Moonlight Studios as the backdrop, this modern-day spectacle shines a light on participating Embarc youth as emerging musicians, aspiring writers, and nextgen change-makers. No rubber chicken dinners here! This anti-gala brings Chicago’s flavor, magic, and creative spirit to life. Your attendance helps grow Embarc’s award-winning curriculum, enabling student success through social and cultural learning. Tickets start at $100, with opportunities to participate in our exclusive Hero Experience or join the host committee. For more details and to purchase tickets, visit Embarcchicago.org/variety2019.
18th Annual Bike the Drive
Sunday | May 26th | 6:00 p.m.
Grant Park | 350 E Monroe St. | Free
Bike 30 miles car-free along Lake Shore Drive during the 18th annual Bike the Drive event. The event benefits Active Transportation Alliance which is a non-profit, member-based advocacy organization that works to make bicycling, walking and public transit safe, convenient and fun. To participate in the event, visit the website here.
The 7th Annual Greenheart Gala: For the 7th Generation
Thursday | May 2nd | 6:00 p.m. – 11:00 p.m.
Garfield Park Conservatory | 300 N Central Park Ave. | $85 – $100
Surrounded yourself in the natural beauty of lush plants and spring flowers at the conservatory, during the 7th Annual Greenheart Gala. During the fundraiser, you will enjoy in-season food, unlimited local beer and wine, KOVAL Distillery whiskey and gin, live music by the Guillermo Paolisso Trio, and an inspiring presentation commemorating our 2019 Global Leader Honoree, Chicago artist Arica Hilton. Interact with local organizations offering resources for sustainable living in Chicago, including The Urban Canopy, loveren collections, and TreeSisters: women seeding change, as well as the Greenheart Odyssey program. To purchase tickets to the event, visit Greenheart.org/event/gala-2019.
Arts + Culture:
Robert Pruitt, Art and Afrofuturism
Wednesday | May 1st | 5:00 p.m. – 7:00 p.m.
DePaul Art Museum | 935 W Fullerton Ave. | Free
Robert Pruitt is an award-winning artist with work that specializes in race and identity. His work creates a narrative surrounding the black body, and is rooted in fictional ethnography. Join us at the DePaul Art Museum to chat with him about the broadness of the Black experience within the Diaspora and the role of Afrofuturistic iconography in his work. Light refreshments will be served and the talk begins promptly at 5:30 p.m. For more details on the artists and the event, visit the Facebook page here.
Do Division Street Fest
Friday – Sunday | May 31st – June 2nd | Time Varies
2000 W Division St. | Free
Do Division, one of Chicago’s most notable summer events rounds out the month of street festivals in May and kicks of summer festivals for June. The signature Chicago street fest pits excellent shopping, live music, and family entertainment together under the summer sun. Check out the full line-up of performers, vendors, and more by visiting the website here.
The Other Art Fair
Thursday – Sunday | May 16th – 19th | Time Varies
Mana Contemporary | 2233 S Throop St. |$13.50 – $30
Saatchi Art’s The Other Art Fair (“The Fair”), a leading international fair championing independent emerging artists, announces the return of its second Chicago edition at Mana Contemporary. I attended last year and had an awesome time! The international art fair makes a four-day stop in Chicago this month showcasing over 120 artists. The artists showcased at The Fair are selected by a panel of art world experts and tastemakers to ensure fair attendees have access to works of high caliber. The Fair also partners with local organizations throughout the weekend such as Little Black Pearl and Greener Future. For tickets to the private viewing on Thursday night or general admission tickets, visit the website here.
Mole De Mayo
Friday – Sunday | May 24th – 26th | 12:00 p.m. – 9:00 p.m.
W. 18th St. and Paulina | Free
Mole de Mayo is one of the city’s most highly anticipated festivals of the season. Now in its 10th year, the festival continues to draw thousands of locals and visitors to Chicago’s historic Pilsen neighborhood for a mole showdown, determining whose version of the Mexican staple is the best in the city. MOLE’ comes from the Nahuatl word MULLI, pronounced (Moe-le) and means “sauce”. The outdoor festival features local restaurants, an open Mercado/Market, three stages of full of live music, plus lucha libre wrestling. This free event is organized and benefits the Eighteenth Street Development Corporation, an organization serving the Pilsen neighborhood for over three decades. Learn more about Mole de Mayo along with the full schedule of weekend events by visiting the event page.