“Chicago is one of the best places in the world from May through October, with all its festivals and events,” says Dave Zimmer, “and the running scene is vibrant year-round.” The Chicago-area native should know. Zimmer and his wife, Lisa, spent the last 28 years opening Fleet Feet stores across the city. And though he admits, “you have to be kind of hardy,” to run through the winters, when it comes to routes, races, and other intangibles, Zimmer says, “Chicago is just fantastic.”

　　Running the Windy City starts with the bustling Lakefront Trail. Extending 18.5 miles along the Lake Michigan waterfront, north and south of downtown, the smooth, flat, and car-free path is a road runner’s paradise. Numerous running clubs offer organized group runs at all hours, seven days a week. The air coming off the lake provides a (slight) respite from humid summer heat, and there’s even a series of hydration stations on weekend mornings from June through October, staffed by Fleet Feet and the Chicago Area Runners Association.

　　Beyond the lure of the Lakefront, there are downtown loops under towering buildings and past iconic landmarks, plus endless targeted neighborhood runs, from touring street art in Pilsen to connecting hip eateries in Northalsted.

　　Routes The Lakefront Trail: It can be accessed from many parts of the city and run in either direction, north or south. “You have the spectacular Lakefront South,” says Zimmer, “where, as you are coming from the South Side towards downtown, the city opens up in front of you.” Locals call the mishmash of paths intertwining just to the south of the city the “spaghetti bowl.” Zimmer recommends heading south from there and through Museum Campus, past the Shedd Aquarium, the Field Museum, etc. “Once you get past McCormick Place,” says Zimmer, “when you turn around, all you see is the skyline in front of you.”

　　The North Side, Zimmer explains, has runners up against the water. And, he adds, “you have Ohio Street Beach, North Avenue Beach, Belmont Harbor, all the way to the end of the path.”

　　The 606: This refurbished rails-to-trails system just north of North Avenue is an elevated path that extends just over three miles. “The beauty of it,” says Zimmer, “is there are parks that you can peel off into.” If you just take a chance and give it a look, he adds, “It’s gorgeous, and so well done, such a great use of space.”

　　Des Plaines River Trail: This suburban soft-surface trail lines the Des Plaines River for just over 34 miles in Chicago’s Lake County, one of its many suburbs. “It’s beautiful,” says Zimmer. “And you can just keep on going north until you hit Wisconsin.”

　　More Options: Probably the most popular of the suburban running areas, according to Zimmer, is the trail system within the Palos Forest Preserve, or just Palos. Some 350 miles of trail weave through the area, varying from paved to gravel, and include notable elevation gain and loss otherwise hard to come by in Chicago. On the west side of the Windy City is the Prairie Path, which cuts through, you guessed it, prairies.

　　Events Bank of America Shamrock Shuffle: This smaller-scale event, held near St. Patrick’s Day each year, is always festive and kicks off the running season in Chicago, says Zimmer. Race weekend includes an 8K run, a two-mile walk, The Mile one-mile race, and no shortage of folks wearing green on the course. All events start and finish in Grant Park.

　　Bank of America Chicago 13.1: With a start and finish line on Chicago’s West Side, in the Garfield Park neighborhood, this race travels through the boulevards, which are green-area medians that link neighborhoods. (The entire boulevard system spans 26 miles.) “It’s just spectacular,” says Zimmer of the race.

　　Soldier Field 10 Memorial Day Run: This ten-mile race on the Saturday of Memorial Day weekend sends runners through Museum Campus and along the Lake Michigan lakefront before finishing on the 50-yard line of Soldier Field, home of the Chicago Bears and Chicago Fire FC. Runners can watch themselves on the jumbotron as they cross the finish line.

　　More Options: The 5K Race to Wrigley Charity Run starts near the home of the Cubs and finishes right in front of the iconic Wrigley Field marquee. Says Zimmer: “Ventures Endurance puts on really cool super-local events like the Bucktown 5K, which goes to the neighborhood of Bucktown. And the Ravenswood 5K on the North Side helps sustain a food pantry.” The Chicago Area Runners Association (CARA) Ready to Run 20-Miler is a point-to-point noncompetitive event along the waterfront and serves as a marathon training run for many.

　　Resources Clubs Fleet Feet Chicago Racing Team: A Chicago staple among running clubs for 25 years, this team is open to all and has coached workouts on Wednesday evenings in the Old Town neighborhood. An Elite Team option is also available.

　　Fleet Feet Running Club: This group hosts seven different group runs in the three-to-six-mile range throughout the city on various days of the week. Brands often demo gear to participants.

　　Endorphins Running: The local chapter of this national running group meets once or twice a week, and always on Monday mornings to start the week off on a good foot.

　　Stores New Balance Chicago, Highland Park: This specialty run store carrying all New Balance goods is known for its excellent customer service.

　　Fleet Feet: Old Town, Lakeview, Lincoln Square, South Loop, Deerfield Elmhurst, Oak Park, Rockford: Dave and Lisa Zimmer’s eight Chicago-area stores serve runners and walkers of all ability levels under the motto “Running changes everything.”

　　Naperville Running Company: NRC North, NRC South, NRC Wheaton, NRC Annex: The locally owned, independent NRC has three locations, plus a track club and a reservable space called the Underground for events like cross-country team pasta parties. Head to the Annex location for closeout deals and limited-run merchandise.

　　Heartbreak Chicago: Located in the Lincoln Park neighborhood and connected to Heartbreak Boston, this store hosts group runs throughout the week and offers a specialty run shopping experience.