A running start

Hyde Park
South Side shuffle
Length 5.5 miles Surfaces Concrete and some gravel (along lake) When to go Weekend mornings or early evenings

In addition to a stunning view of the skyline, you’ll get a quick tour of the University of Chicago and the site of the famed White City. The run begins just south of the U. of C. campus, on the Midway, where parking is free 24/7.

Jimmy’s Woodlawn Tap (1172 E 55th St) The U. of C.’s local watering hole

Medici Bakery (1331 E 57th St) Huge stuffed croissants and coffee

Start at the Masaryk Memorial Statue (1). Thomas Masaryk taught at the U. of C. before becoming Czechoslovakia’s first president in 1920. Run west on the Midway Plaisance, the site of the carnival-style midway of the 1893 World’s Columbian Exposition (and also the site of the first Ferris wheel) (2). Turn right (north) on Woodlawn Avenue and on your left is the neo-gothic Rockefeller Memorial Chapel (3). Continue north and pass the Graduate School of Business (4) and the Robie House (5). The Robie House is a fine example of Frank Lloyd Wright’s Prairie School of architecture, and Rafael Viñoly echoed that design with his 2004 GSB building. Turn left (west) on 57th Street, then turn right (north) on Ellis Avenue and you’ll run by Henry Moore’s “Nuclear Energy” sculpture (6) between 56th and 57th streets, marking the site of the first self-sustaining nuclear reaction. Turn right (east) on 56th Street and check out the (7) Keck-Gottschalk-Keck Apartments (5551 S University Ave). This innovative three-flat in Mies Van der Rohe’s International Style was granted landmark status in 1994. At the lakefront, turn left (east) and round the easternmost part of (8) Promontory Point as the skyline comes into view. As you head back south on the path, you’ll be circling the original site of the lagoons and build-ings of the Exposition’s “White City.” The only remaining building from the fair is the Museum of Science and Industry (9). Take Cornell Drive back to the Midway.—Marc Geelhoed

Humboldt Park

Boulevard run This loop is perfect for a nature lover with tender shins. The whole run can be done on grass, taking advantage of Chicago’s boulevard system, and features a tree-lined straightaway, lush fields, a lagoon and an impressive formal garden.

Length 3.3 miles Surface Grass (asphalt at street crossings) When to go Sunday mid-morning

Streetside Café (3201 W Armitage Ave) Beer and mini-pizzas

The Flying Saucer (1123 N California Ave) Try the biscuits with gravy (sausage or mushroom).

Start heading east on the wood-chipped footpath at Palmer Square’s northwest corner, or run up the sidewalk across the street to get a better look at the turn-of-the-century homes (1) lining the square. Head south along Humboldt Boulevard. At North Avenue, you’ll enter Humboldt Park (2). Continue along Humboldt Boulevard, a.k.a. Sacramento Avenue, as it curves through the park. On your left you’ll see the large Humboldt Park Lagoon (3) and the boathouse (4) (301 N Humboldt Blvd) designed by Prairie School architects Schmidt, Garden and Martin in 1906. Just before you reach Division Street, check out the formal garden (5) on your right—its entrance is flanked by two giant buffalo statues. Turn right (west) at Division Street and then follow Brenock Drive along the western edge of the park. As you curve back up to North Avenue, you’ll pass behind the Illinois National Guard Armory building (6). Make a left (north) at Humboldt Boulevard and run up the other side of the road for variety’s sake, back to Palmer Square.—Ruth Welte

Downtown

Architecture tour
Length 5 miles Surface Concrete sidewalks When to go Late evening, after all the Loop workers have gone home; weekends

Take in the history of skyscrapers, from one of the first, built in 1883, to Trump Tower, still under construction. Set out in the early evening, when Loop workers are scarce and the sun is setting on the steel and glass windows.

Chicago 101
Length 3.7 miles Surfaces Concrete, asphalt and grass When to go Weekdays 5–7pm; Saturday and Sundays 6–10am

Whether you’re a visitor or a townie, we guarantee you’ll be awed by a view of the skyline that most lakefront-path veterans never see. In under four miles you’ll make some major progress on the sightseer’s to-do list.

Park Café (11 N Michigan Ave) Coffee, snacks and sandwiches

17 West (17 W Adams St) The former Berghoff bar

Kitty O’Shea’s (720 S Michigan Ave) A laid-back Irish pub, no shower necessary

Start at the 1883 Monadnock Building (1) (53 W Jackson Blvd), the last skyscraper made without steel (back when “skyscraper” meant 11 stories). Head north on Dearborn Street and you’ll enter the Mies van der Rohe Federal Center (2) (Dearborn St between Jackson and Adams Sts) with its orange Alexander Calder sculpture. Take a right (east) on Monroe Street and hit Carson Pirie Scott (3) (1 S State St), Louis Sullivan’s masterpiece. Continue north on State and check out the iconic buildings across the river: Bertrand Goldberg’s “corncob” Marina Towers (4) and Mies’s IBM Building (5), soon to be hidden by the Trump Tower (6), swiftly rising to its 90-story height. Turn right (east) on Wacker Drive and hit the Michigan Avenue bridge, where you’ll take the stairs to the riverwalk for skyline views. Turn left and head west along the river. At the bend, look across the water: Graham, Anderson, Probst & White’s 1931 Merchandise Mart (7) boasts its own zip code. And 333 Wacker Drive (8) is a favorite for its spectacular curving glass facade. Double back, up the riverwalk, and ascend the stairs at Michigan Avenue. Take a look at the Wrigley Building (9) (410–420 N Michigan Ave) with its 250,000 terra-cotta tiles. Run south beside the Michigan “streetwall,” then take a right on Jackson Boulevard and continue west. The mammoth structure to the right is the Sears Tower (10) (233 S Wacker Dr). Turn right (north) on Wacker Drive and go to Adams Street, then turn right (east) again. At Adams and LaSalle streets, see the Rookery (11) (209 S LaSalle St), Burnham & Root’s building with a Frank Lloyd Wright–designed lobby. Continue east on Adams, turn right (south) on Dearborn Street, and end where you started. —Madeline Nusser

Start at the Cloud Gate (1) sculpture, aka “The Bean,” in Millennium Park. Head east on the park’s path around the Great Lawn toward Frank Gehry’s shiny, snake-like BP Bridge (2) (his only bridge to date). Cross Columbus Drive over the bridge, go south along Columbus, then turn left (east) at Monroe Street, crossing with the traffic light. Follow the lakefront sidewalk south along Lake Shore Drive all the way to the Shedd Aquarium (3). You’ll see Solidarity Drive, a divided parkway, with trees and flowers planted in the middle. Turn left (east) until it dead-ends at the Adler Planetarium (4). Face northwest for a spectacular view of the skyline and lake. Oooh and ahhh, then turn and run back the way you came.—Liz Plosser

North Channel Trail

World in motion On a recent run we spotted a virtual U.N., what with Jews offering up Rosh Hashanah prayers at the banks of the Chicago River, Latino families playing footie and Asian kids swatting at a volleyball, all within this massive green space in the middle of the city.

Length It’s easy to customize your route with jaunts of 3,6 or 9 miles. Surface Asphalt When to go This path is rarely overrun, so anytime is a good time. It’s not well-lit, though, so plan to finish before sundown.

Ben Tre (3146 W Touhy Ave) The beef noodle soup will hit the spot.

Charcoal Delights (3139 W Foster Ave, 773-583-0056) A great place to gorge on brats, fried chicken or ribs.

The North Channel Trail is biker-friendly, so you’ll just have to share. But there’s just too much natural beauty, including a rebounding Chicago River and grassy park after park, to surrender the path to those two-wheelers.Start your jog at Argyle Street and Francisco Avenue (1), and do about three miles up to Touhy Avenue and three miles back. For a run that’s a total of three miles, turn back at Peterson Avenue instead. If you’re feeling extra caffeinated, you can finish your run with wind sprints on North Park University’s excellent rubberized track, which is open to the public (2). Or, for a more leisurely day, catch a football game at North Park’s Holmgren Field (3) (3100 W Foster Ave). If that name sounds familiar, it’s because the stadium is named after the former Green Bay Packers and current Seattle Seahawks coach Mike Holmgren (who’s a dead-ringer for a walrus). The NPU Vikings will look to bull rush the Wheaton College Thunder there Saturday 21 at 1pm (come on—tickets are a measly $5).

The path is just a stone’s throw from (4) Thillens Stadium (Devon and Kedzie Aves), where you might spy the next Derrek Lee in the peewee leagues. Feeling ambitious? Run north along McCormick Boulevard to see the Skokie Northshore Sculpture Park (from Touhy Ave to Dempster St) (5). Must-sees in this alfresco “museum” include Maurice Blik’s Second Breath, Ted Gall’s Sun Worshipper and Patrick McDonald’s Weeee (you’ll understand the title when you see it). If you go to the end at Dempster Street, it’s a nine-mile run, all told.

Thankfully, the run is void of commercial intrusion—unless you count the Lincolnwood mall (who knows, maybe you need a new loofah from Bath & Body Works) or its industrial park. Sadly, Lincolnwood has long since shed its reputation as a “saloon-infested” town, when it was known as Tessville. Just listen to Mother Nature’s sweet song (you’re there to run, right?) and enjoy the fact that most running fools stick to the overcrowded lakefront.—Tim McCormick

Pilsen and Chinatown

8Ks of culture Art and culture lovers can get their fill of ethnic eats and sights in this run. While mostly flat, the route does change elevation by crossing two huge bridges over the Chicago River.

Length 5 miles Surface Concrete sidewalkWhen to go Late afternoon

Laredo Bakery (1540 W 18th St) Try sweet pan de huevo.

Joy Yee’s (2159 S China Pl) Bubble-teas made from fresh fruit

Take the Pink Line to the Damen El stop. On the north side of the train stop, glance at local artist Juan Chavez’s Pilsen-themed mural (1)—the perfect intro to this artsy Latino neighborhood. Go north on Damen Avenue, turn east on 18th Street and peep into the art-filled spaces like painter Rodrigo Alverez’s studio (2) (1255 W 18th St). Make a right on Halsted Street and check out art studios like Dubhe Carreño’s (1841 S Halsted St) ceramics gallery (3). Turn east on Cermak Road and you’ll get a slight change in elevation by heading under the highway and over a bridge in this industrial zone. Emerge in Chinatown and turn north on Wentworth Avenue; loop around the animal sculptures (4) that represent the Chinese Zodiac signs—be sure to read the plaques. Continue north on Wentworth Avenue, take a left on Cullerton Avenue and head into Chinatown Square. Marvel at the bright posters advertising heaping plates of Szechuan pork and lo mein. Head out on Princeton Avenue, turn east on Cermak Avenue, and go south on Wentworth Avenue through the Chinatown Gate (5). Check out the many tea and herbal-medicine shops, Chinese groceries and bakeries (and maybe even stop in for a quick treat). Around 24th Street, double back up the other side of the street to see more Chinese wares. Cross Cermak and take a left at 19th Street, which dead-ends at the pagoda (6) in beautiful Ping Tom Park. Run north through the park until you hit 18th Street and turn left. Go southwest on the diagonal Canalport Avenue until you end up back on Halsted Street in Pilsen.—Madeline Nusser