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Chicago’s May Calendar of Events

A list of Chicago’s best May events.

Things to Do in May in Chicago:

Garfield Park Conservatory Spring Flower Show

When: end of February through the first week of May
Neighborhood: Garfield Park
Address: 300 North Central Park Ave

This flower show runs for about six weeks, from the end of February through the start of May. Each year a different theme is presented; the 2022 theme was “Knock Knock” and the floral displays incorporated doors from the Rebuilding Exchange and knock-knock jokes.

Lincoln Park Conservatory Spring Flower Show

When: end of February through the first week of May
Neighborhood: Lincoln Park
Address: 2391 North Stockton Drive

Like the Garfield Park Conservatory Flower Show, this flower show has a new theme each year. The 2022 theme was “Pillars of Spring” and focused on vertical planting.

Cinco de Mayo Pilsen Cantina Crawl

When: May 7, 2022
Neighborhood: Pilsen
Address: 18th Street

A 21+ event on Saturday, May 7, 2022, where attendees get to taste mezcal cocktails and enjoy live music at bars and restaurants on 18th Street.


When: May 20-22, 2022
Neighborhood: Lincoln Park
Address: Armitage and Sheffield

This three-day street fest kicks off Chicago’s summer festival season. Mayfest has two stages of live music and a menu that includes sangria and summertime food. Bands including 16 Candles, Too Hype Crew, Hairbangers Ball, and the Alan Gresik Swing Orchestra will be performing. The Kid’s Area will host Disney Character Storytime, games, crafts, and activities.

Lincoln Roscoe Art & Craft Fair

When: May 21-22, 2022
Neighborhood: Roscoe Village
Address: Roscoe Street to School Street

A new festival taking place on Lincoln Avenue from Roscoe Street to School Street highlighting over 60 local artists, makers, and independent shops.


When: May 21, 2022, registration at 7:30 am, walk at 9 am
Neighborhood: Museum Campus
Address: 1410 Museum Campus Drive

A 2.5-mile dog-friendly walk along the lakefront that raises money for the Anti-Cruelty Society.

Wright Plus

When: May 21, 2022
Various Neighborhoods
Cost: $125 and up

A one-day event when the interiors of eight private residences designed by Frank Lloyd Wright and his contemporaries are open to the public. Guides are on-site to speak to the history and design of the homes. *Tickets need to be purchased in advance online and they do sell out.

Renegade Craft Fair

When: May 21-22, 2022
Neighborhood: Andersonville
Where: Clark Street

A massive market bringing together artisans, craftspeople, and other local makers. The spring event takes place on Clark Street in Andersonville on May 21-22, 2022.

Mole de Mayo

When: May 27-28, 2022
Neighborhood: Pilsen
Address: 18th Street and Ashland Avenue

Taking place May 27-29, 2022 at 18th Street and Ashland Avenue in Pilsen, Mole de Mayo combines live music, dancing, art, lucha libre wrestling, and an outdoor mole cook-off. During the event, local restaurants and chefs compete to win the titles of “Best Mole” and “People’s Choice.”

Memorial Day Parade

When: May 28, 2022 at noon
Neighborhood: The Loop
Address: State Street from Lake Street to Van Buren Street

This parade starts with a wreath-laying ceremony at Daley Plaza.

Navy Pier Fireworks

When: May 28, 2022
Neighborhood: Streeterville
Address: Navy Pier

Fireworks are set off from Navy Pier on Wednesdays and Saturdays from Memorial Day until Labor Day. In 2022, the first night of fireworks will be Saturday, May 28th.

Sueños Music Festival

When: May 28-29, 2022
Neighborhood: the Loop
Address: Grant Park

A Latin music festival featuring over 15 Latin and Raggaeton artists, Latin food, bars, and a Ferris wheel. This festival is 18+.

Belmont-Sheffield Music Festival

When: May 28-30, 2022
Neighborhood: Lakeview
Address: the intersection of Belmont and Sheffield

Local bands including Rod Tuffcurls & the Bench Press, Trippin’ Billies, and Boy Band Review are all playing at this weekend street fest. Some of Chicago’s most iconic drag performers will be featured on the Belmont Stage on Sunday at 8:45 pm.


When: May 28-29, 2022
Neighborhood: Ravenswood
Address: the corner of Ravenswood and Belle Plaine Avenues
Cost: $5 donation to The Friendship Center

Chicago craft breweries Dovetail Brewery and Begyle Brewing co-host this all-ages festival with beer, live music, and food trucks.