#1 Sports Event
Some 40,000 runners participated in this year’s massive race. Traveling through 29 Chicago neighborhoods, the event drew around 1.7 million spectators and was covered in national publications including Newsweek. Bank of America is the presenting sponsor. Next: October 8, 2017
#2 Sports Event
Jockeys, horses, and trainers from all over the world gather at the event, which is known as the first event of its kind to offer a million-dollar purse. This year, a crowd of about 32,000 spectators watched as Mondaliste was named the winner. Next: Summer 2017
#3 Sports Event
Sponsored by Bank of America, the eight-kilometer road race passes through downtown Chicago, and starts and finishes in Grant Park. The shuffle is regarded as the unofficial kickoff to the city’s outdoor running season, and many participants don festive green running gear. This year, about 23,000 runners participated. Next: April 2017
#4 Sports Event
Held over Memorial Day Weekend, the early-morning bike ride takes place along a 30-mile stretch of Lakeshore Drive. Local cyclists bike down a car-free road to raise money for the Active Transportation Alliance. The event typically draws some 20,000 cyclists. Next: May 2017
#5 Sports Event
Special Olympics of Chicago broke its fund-raising goals in 2016 by raising some $1.5 million. The event also drew record participation, with some 6,000 guests plunging into the icy waters of Lake Michigan. Only 4,500 “plungers” attended in 2015. This year’s event saw several celebrity attendees—including Lady Gaga and Al Roker of NBC's Today show—and it also saw higher levels of corporate sponsorship. Next: March 5, 2017
#7 Sports Event
Held on the shores of Lake Michigan, the competition is one of the largest triathlons in the world. In 2016, the event had more than 2,500 new participants, contributing to a total of more than 9,000 competitors. Some 30,000 spectators cheered the athletes on, and Transamerica was once again the title sponsor. Next: August 27, 2017
#8 Sports Event
Despite windy, rainy weather, this year’s attendance stayed steady with some 2,500 runners. The event raked in more than $471,000 this year, which marks an increase over the $386,000 raised last year. The event’s opening ceremonies included a live performance from the Chicago Gay Man’s Chorus. Next: Fall 2017
#9 Sports Event
Chicago’s largest nighttime biking event draws some 8,000 cyclists each year. The 25-mile ride kicks off at 10:30 p.m. with a pre-ride festival that includes live music, vendors, and contests for achievements such as “best decorated helmet.” This year, new attractions included a 4:30 a.m. “sunrise stretch,” hosted by Gratitude Yoga. Next: Summer 2017
#10 Sports Event (up from #11)
Billed as one of the oldest freshwater races in the world, the event celebrated its 108th anniversary in 2016. The 333-mile race kicks off at the Chicago Lighthouse, just east of Navy Pier, and ends at Mackinac Island. Participation is by invitation from the Chicago Yacht Club, and 326 boats participated this year. Parties include Michigan Avenue’s Ashore Thing presented by BMO Bank, which lets fans view the race from Navy Pier while sipping champagne. Next: July 2017
#11 Sports Event
The event combines a 5K, pet-friendly walk with a 5K run (the latter is “for humans only.”) Kicking off at Montrose Harbor, the event benefits homeless animals and lured around 3,000 participants—and 1,000 pups—this year. Attractions also includes splash pools for dogs, a “doggy buffet,” food trucks, and face painting. Next: Summer 2017
