Start Red Line, Clark/Division stop End Red Line, Chicago stop
Walking time About 2 hours Distance 3.2 miles
1 Legend has it the Gold Coast got its name when developer Potter Palmer (think Palmer House Hotel) bought up North Side swampland after the Chicago Fire and persuaded prominent businessmen to build homes so opulent that regular Joes surmised gold was dripping from these rich guys’ pockets. To decide for yourself, stroll three blocks east on Division Street, turn left on Astor Street and head north.
2 Fast-forward to 1963 on the corner of Astor and Goethe Streets by peeking in at Maxim’s: The Nancy Goldberg International Center(24 E Goethe St, lower level, 312-742-1748, maximschicago.org), an exact replica of the famed Art Nouveau–style Parisian restaurant. Take a quick look around the dining room’s elaborate interior with its stained glass, dark wood and brass accents. During its heyday as Chicago’s most exclusive hot spot, founder-proprietress Goldberg hosted Margot Fonteyn, Eartha Kitt, the Beatles, King Peter of Yugoslavia and other celebrities.
3 Ease back into the 19th century as you continue north on Astor Street with stops at the 26-room Graham Mansion(25 E Banks St), which is for sale at $10.5 million; the Charnley-Persky House Museum(1365 N Astor St, 312-915-0105; free tours Wednesdays at noon), an early collaboration between Louis Sullivan and Frank Lloyd Wright; and the Patterson-McCormick Mansion(1500 N Astor St), designed by Stanford White, a notorious womanizer who was murdered in 1906 at the old Madison Square Garden—which he also designed—by the jealous husband of actress Evelyn Nesbit.
4 You may be feeling envious of all these rich abodes, though it might help to know the area was temporarily declared a slum through the Land Clearance Act of 1948. Walk one block north on Astor Street, turn left at North Avenue and pass the Archbishop’s Residence(1555 N State Pkwy), a Victorian mansion featuring 19 chimneys where President Franklin D. Roosevelt was an overnight guest.
5 Once you’re straight with the saints, turn left on State Street, walk three blocks south and pay homage to debauchery at the original Playboy Mansion(1340 N State Pkwy). The building now houses luxury condos, but during Hugh Hefner’s tenure, a sign by the doorbell read IF YOU DON’T SWING, DON’T RING.
6 Swing back one block north to Schiller Street, turn left, walk one block west to Dearborn Street, turn right and head north to another legendary crash pad, The Second City cofounder Bernie Sahlins’s residence(1525 N Dearborn St), where comedians Bill Murray and John Belushi often partied—and passed out—in the early ’70s.
7 Now head south on Dearborn, east on Division and south on Rush to take your CTA budget to the ritzy Oak Street shopping district: Turn left on Oak, walk 2½ blocks east and stop at Sarah’s Pastries & Candies(70 E Oak St, 312-664-6223), where Martha Stewart occasionally shops. Be sure to try the cupcake of the month ($2.99). Or snag vintage and couture resale deals at the Daisy Shop(67 E Oak St, sixth floor; 312-943-8880, daisyshop.com), including a vintage red-leather medicine travel kit with bottles, spoon and thermometer for $40.
8 Walk east on Oak Street to the Lake Shore Drive curve, head south on LSD three blocks to Chestnut Street and turn right to get to Le Petit Paris(260 E Chestnut St, 312-787-8260, lepetitparis.net), a cozy, ’60s-style bistro hidden inside a condo building lobby, where cocktails arrive in retro glassware and the ladies’ room decor includes pink poodles—Don and Betty Draper would fit right in. Now, step back into the double-aughts with a six-block stroll west on Chestnut Street, turn left at State Street and walk two short blocks south to the Chicago Avenue El stop.
GO THE EXTRA MILE Head to the International Museum of Surgical Science(1524 N Lake Shore Dr, 312-642-6502, imss.org; $10, free Tuesdays), where oddities include an iron lung, a plaster cast of Napoleon’s death mask and a collection of gallstones.