#2 Sports Event
The event is one of the richest horse races in the world: reportedly, it was the first such event to offer a $1 million purse. The high-end function draws horses, trainers, and jockeys from across the globe. Some 32,000 guests attend annually, and the race is broadcast on national TV. Next: August 16, 2014
#3 Sports Event
Sponsored by Bank of America, it's the word’s largest 8K road race and is now in its 35th year. The fun, quirky spirit is underscored by runners dressed in costumes, including green tutus and sparkly leprechaun hats. This year, the event had 30,000 runners and culminated with a post-race party in Millennium Park. Next: March 2015
#4 Sports Event
About 30 miles of Lake Shore Drive are closed off to car traffic on the morning of the sporty event, which raises funds for the Active Transportation Alliance. This year, 20,000 cyclists pedaled the clear stretch of Chicago’s iconic road. Next: May 2014
#5 Sports Event
In 2014, the race took place on Mother’s Day and included a 10K timed run, a 5K timed run, a 5K walk, and a one-mile fun walk. The event typically draws around 7,600 participants, who don pink in honor of the event’s cause. This year’s event included performances, family-friendly activities, and a survivors’ parade. Next: May 2015
#6 Sports Event
One of the country’s largest triathlons, the summertime function draws 7,000 athletes and is presented by Toyota. In 2013, the event saw some changes: it introduced a new competition called the “Chicagoland Tri Series,” and there was also a new team challenge. There will be more changes this year, including a 10K SuperSprint bike that lets participants use Chicago’s bike-sharing system Divvy. Next: August 24, 2014
#7 Sports Event
In 2013, the event set a record by raising $400,000 by the time the race stepped off. Additionally, its sponsorship dollars more than doubled from 2012. Performer CeCe Peniston appeared at the post-race festivities. This year’s event kicks off at Arvey Field in Grant Park. Next: September 14, 2014
#8 Sports Event
Kicking off at 1 a.m., Chicago’s largest nighttime biking event sets off from Buckingham Fountain and wends through a dozen neighborhoods. The noncompetitive event lures 8,000 cyclists, and participants are encouraged to add light-up trimmings to their helmets. This year’s theme was “Light Up the Night,” and all participants received glow-in-the-dark shirts and necklaces. Next: June 2015
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#9 Sports Event
More than 7,300 people plunged into the freezing waters of Lake Michigan to raise funds for the Special Olympics this year. The chilly event, which is presented by Geico, has plunges in 20 locations throughout Chicagoland. It raised more than $2 million this year, which is more than the $1.7 million raised in 2013. Next: Winter 2015
#10 Sports Event
With a 333-mile route, the summery affair is the world’s longest annual freshwater race. In 2013, the competition saw 301 boats and 2,472 crew members racing to Mackinac Island. The event, which was founded in 1898, has a glitzy pedigree: Participation is by invite from the Chicago Yacht Club, and Veuve Clicquot is the presenting sponsor. Next: July 19, 2014
#11 Sports Event
Held at Montrose Harbor, the animal-friendly event draws around 6,000 runners and walkers—and their pooches. The funds raised benefit the organization’s life-saving programs for pets, and the day includes an 8K run and a 4K walk, and fun attractions include a “canine carnival.” Next: June 2015
