My wedding anniversary is in the third week of May, and I have always used that date to know when I can finally count on great weather in Chicago.
Find wonderful ways of enjoying it with this calendar of May events. Check back often as new annual events are always being added.
May Highlights: Mother's Day | Opening of the Art Institute's Modern Wing | Memorial Day Weekend
- Spring Flower Shows - Through May 10
The Lincoln Park Conservatory and the Garfield Park Conservatory spring into full bloom with their annual flower shows. - Arlington Race Track Opening Day - Friday, May 1
Just in time for the Kentucky Derby, Chicagoland's elegant horse racing facility opens for the season.
- Cinco de Mayo Festival and Parade - Friday, May 1 to Sunday, May 3
More than 200,000 people attend this family-oriented celebration every year in Douglas Park (1401 S. Sacramento). The parade runs on May 3 beginning at noon on Cermak and Damen and heading west to Marshall Blvd.- 3rd Annual Teen Comedy Fest - Saturday, May 2
The Chicago Park District and the Chicago Impov Festival team up to showcase 11 teen teams from 5 states.- Poland in the Park - TBD
A celebration of Polish culture beginning with a parade at followed by a fest in Millennium Park. Features music, food, and entertainment. - Midwest Anime & Manga Convention - Friday, May 8 through Sunday, May 10
The Donald Stephens Convention Center hosts the 12th annual Anime Central festival. What is Anime? | What is Manga? - 17th Annual Chicago River Day - Saturday, May 9
Join with thousands of other volunteers in the morning to help clean the Chicago River, then join them for a mega-BBQ at River Park (5100 N. Francisco) in the afternoon. - National Train Day - Saturday, May 9
Enjoy "trainiac" festivities at Union Station from 10 a.m. to 3 p.m. - Chicago Climate Cycle Ride - Saturday, May 9
A new event on the Chicago landscape raises money to help install solar panels and to support sustainable education in local public schools. 12 and 25 mile routes available. - Mother's Day - Sunday, May 10
Love your mama. Find Chicago events and gift ideas to celebrate mom. - Bridgehouse and Chicago River Museum - Opening Day - May 15
Chicago's unique museum in the southwest tower of the Michigan Avenue bridge opens for summer. See photos here. - 43rd Annual Bloomin' Sale - Friday, May 15 to Sunday, May 17
Dig into the gardening season with the Chicago Botanic Garden's popular annual event. - Chicago Places and Spaces Festival - Saturday, May 16
Another name for this might be "Urbanist Fest." Come tour the city's architectural gems and neighborhood wonders through this celebration of our urban landscape. - Art Institute of Chicago - Opening of the Modern Wing - Saturday, May 16
Chicagoans will get a peek at the highly-anticipated opening of the new Modern Wing and the Nichols Bridgeway that will connect the museum to Millennium Park. - Chicago Green Festival - Saturday, May 16 and Sunday, May 17
Tap into the city's green vibe and re-commit to a sustainable lifestyle at this Navy Pier event. Yoga. Organic Beer. Speakers. Eco-friendly products. - Chicago Bears EXPO - Sunday, May 17
Because you know, in a small way, you just can't wait until winter. - Second Annual Andersonville Wine Walk - Sunday, May 17
This sounds to me like a lovely way to spend an afternoon. - International Mr. Leather - Thursday, May 21 through Monday, May 25
Celebrating 31 years of hot and hunky. - International Gem & Jewelry Show - Friday, May 22 to Sunday, May 24
The Donald E. Stephens Center in Rosemont hosts a giant gem and jewelry show so you can stock up on your bling. - 11th Annual Asian American Festival - Monday, May 18 through Friday, May 22
Cultural performances, food, market and more every day in Daley Plaza. Hosted by the Filipino-American community of Chicago. - Memorial Day Weekend - Friday, May 22 to Monday, May 25
Find a listing of some of the key events of the opening weekend of summer. - Chicago's Memorial Day Parade - Saturday, May 23
Remember, honor, and enjoy at the downtown Chicago Memorial Day parade. - Chicago Antique Market Opens - Saturday, May 23 and Sunday, May 24
The city's European style antiques market kicks off its summer season. - Bike the Drive - Sunday, May 25
Lake Shore Drive is one of the loveliest drives in the world - why not bike it in this car-free, friendly event? - 24th Annual Chicago Career Conference - Hispanic Alliance for Career Enhancement (HACE) - Wednesday, May 27
This expanded networking opportunity takes place at McCormick Place South. - 2nd Annual Athens Sister City Shuffle - Thursday, May 28
Fortunately, it's just a 5K run through Greek Town rather than to our sister city of Athens. - Mayfest - Friday, May 29 through Sunday, June 1
Lincoln Square's annual summer celebration with a German flair.
