1. Chicago Marathon
More than one million spectators are expected to line the streets of Chicago on October 12 to cheer on the 45,000 entrants in the 31st annual Chicago Marathon, presented by Bank of America. This race annually raises more than $10 million through the 6,000 charity runners who participate. It is part of a three-day Health and Fitness Expo at Navy Pier, which will see more than 125,000 visitors. A post-race party is open to all of the event’s competitors.
2. Race to Mackinac
Navy Pier will be teeming with boats on July 19, as a record 460 vessels make the 333-mile trek to Michigan’s Mackinac Island as part of the 100th anniversary of this race. The Chicago Yacht Club presents what it boasts as the longest freshwater race in the world. This year, Donald Wilson will captain the Stars and Stripes, which set the record for fastest time in 1998, crossing the finish line at 18 hours, 50 minutes, and 32 seconds.
3. Arlington Million
The name says it all: Horse jockeys, trainers, and owners will descend on Arlington Park on August 9 to win their share of a $1 million total purse in one of the most prestigious races in the country. The 26th annual Arlington Million is Arlington Park’s signature event and typically attracts 32,000 visitors to the racetrack. The big race will dole out $60,000 to the winner and be broadcast live on national television.
4. Mayor Daley’s Holiday Sports Festival
In 2000, Mayor Richard Daley kicked off Holiday Hoops, a basketball tournament for schoolkids from throughout the city. Now renamed the Holiday Sports Festival, the three-day event at McCormick Place is set to attract 85,000 participants and includes daily demonstrations, interactive zones like climbing walls, skateboarding ramps, and sports clinics, and a series of basketball, floor hockey, tennis, and volleyball tournaments. The Mayor’s Office of Special Events produces the event, and sponsors of the festival include Blue Cross Blue Shield, Pepsi, and Hinckley Springs. The 2008 event takes place December 27 to 29.
5. Bike the Drive
More than 20,000 bicyclists take over Lake Shore Drive for the annual Bike the Drive, sponsored by Bank of America. Starting at 5:30 a.m., cars are prohibited on the 30-mile stretch from the Museum of Science and Industry on 57th Street to Hollywood Avenue on the north in a glorious display of spoke-and-wheel splendor. Beatles tribute band American English played at a kid-friendly post-race party for the 2008 event, which took place May 25.
6. Susan G. Komen Race for the Cure
Part of the national Race for the Cure circuit, Chicago’s event—held in Grant Park on September 27—is expected to garner more than 10,000 participants, including 600 breast cancer survivors and 500 volunteers, in its 12th year. The race features a 5K run/walk and a one-mile fun walk. The 2007 event raised $575,000 for the Susan G. Komen Foundation, which funds breast cancer research.
7. Special Olympics Inspire Greatness Gala
Forty years ago, a small group got together in Chicago to celebrate the athletic achievements of those with intellectual and physical disabilities, creating the Special Olympics organization. The group is celebrating its milestone this year at its annual fund-raising gala at the Chicago Hilton on July 19, which aims to raise more than $500,000 to help fund the more than 170 annual competitions. Chicago Mercantile Exchange chair Terry Duffy will host the event, which will feature music by the City Lights Orchestra and a sports-themed silent auction.
8. AIDS Run & Walk Chicago
You can find a charity race in the city just about any weekend, but few help a cause more directly than the AIDS 5K Run & Walk, held this year in Grant Park on September 20. More than 7,000 participants will walk and run. Last year, $420,000 was raised to help eradicate the disease. A family-friendly post-run party will feature local dance crew Chicago FootworKINGz.
9. Run for Their Lives
More than 3,000 pet lovers will convene on Montrose Beach for the Run for Their Lives 8K Run/4K Walk on September 28. The event, in its eighth year, expects to raise nearly $450,000 for Paws Chicago, which strives to find homes for strays and helps keep them healthy. Post-race activities include a dog agility competition, a pet fashion show, and a canine carnival.