Chicago's marathon, one of the majors, is widely considered a flat and fast course that's ideal for first-time marathoners or those looking to set personal bests or qualify for Boston. One way to target your ideal time is to run with a Nike Pace Team, a free service that allows you run alongside experienced marathoners targeting finish times every five minutes between 3:00:00 and 5:45:00. The marathon draws a crowd that's nearly as large as New York's, and, as in New York, spectators line the streets on most of the route, which winds its way through most of Chicago's neighborhoods, including Lincoln Park, Little Italy, and Chinatown. The second half of the course has fewer turns, so if you've been training properly, you can expect to have negative splits.

More Information: There are no qualifying times for Chicago, but the event is capped at 45,000 participants. [Early October;]