The Best Walks in the 10 Most Walkable U.S. Cities
Acres and acres of parkland and the banks of Lake Michigan make the Second City a shoo-in for one of America’s most walkable
locales. “Chicago is a good walking city simply because it’s flat: You can walk for miles with hardly any effort,” says Ryan
Van Berkmoes, author of Walking Chicago ($20, amazon.com). “But it’s the architecture, neighborhood flavors, beauty, and endless surprises and discoveries that make it a great walking
Best Walk: Washington Park and Jackson Park
This four-mile stroll is particularly lovely on a sunny day, says Van Berkmoes. Start in the northwest corner of Washington
Park, at 51st Street and Martin Luther King Drive. Head south on the park’s tree-lined path to 55th Street, then turn left
to cross over Ellsworth Drive and head east along the main road. Cross Rainey Drive and walk south along Morgan Drive to the
DuSable Museum of African American History. From here, follow the curving path south through the park, joining up with Payne
Drive just before the Fountain of Time sculpture. Walk east from the fountain into grassy Midway Plaisance, which stretches
almost a mile. Cross under the railroad tracks near 59th Street and continue east to enter Jackson Park. Cross South Stony
Island and South Cornell Avenue; about 350 feet later you’ll come to a fork in the road. (You should see the lagoon ahead
and to your right.) Follow the path to the right over the bridge to Wooded Island, where you'll pass the Japanese Osaka Garden.
Keep an eye out for birds and wildlife as you walk south to cross the bridge at the far end of the island, continuing onto
East Hayes Drive. Turn left and continue over a small bridge, then veer north on a narrow trail that curves back up along
the lagoon and past the park’s driving range. Finish your walk by continuing north over another bridge to the parking lot
at Columbia Drive or exiting the park at 59th Street to catch a city bus. To access the map, click here.
Alternate Walk: Grant Park to Northerly Island
Start this 4.1-mile walk at the southeast corner of Monroe Street and Columbus Drive. Cross diagonally through the wide-open
spaces of Butler Field, then pick up the path just east of the bandshell and cross over East Jackson Drive. Walk up the steps
to Buckingham Fountain and its reflecting pool. Turn right to walk west along East Congress Parkway and cross over the Metra
train tracks, then turn left to follow the park south between Michigan Avenue and the train tracks. At East 9th Street, climb
the hill to the monument of General John Logan. Turn right to follow the walkway south from the monument to a pedestrian bridge
over the train tracks. Continue east on the bridge and follow the curve down and under Columbus Drive. Walk south to the statue
of Christopher Columbus, then north over the grass to a wide walkway that leads to the Museum Campus, a 57-acre park that
surrounds three of the city’s science museums. Take the Lake Shore Drive underpass to the Museum Campus, then cross the plaza
and loop around the Shedd Aquarium. From here, head east to the Adler Planetarium, then turn right to take the narrow walkway
down to the 12th Street Beach. You’ll find a path that runs south through the heart of Northerly Island. Follow this outer
loop down the east side of the island and back up the west side, ending your walk on South Linn White Drive and East Solitary
Way, where you can catch a bus back to your starting point.
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