CHICAGO is a minx. She draws you in with her sleek architecture, gastro-fab food, and up-to-the-minute fashion. Then, in the blink of an eye, she delivers a new perspective, one steeped in the Carl Sandburg style of old-school tradition and integrity. To really appreciate the Third Coast, you have to delve into the historic nooks and crannies that speak to the charm of a bygone era.
Diners, Delis, and Dogs (and One Bar)
Manny’s Coffee Shop & Deli, politicians, cops, and A-list noshers wait in line for heaping delicatessen sandwiches doled out cafeteria style. Famous for corned beef, brisket, pastrami, crispy potato pancakes, and stuffed cabbage, Manny’s has remained virtually unchanged since 1942. 1141 South Jefferson Street, (312) 939-2855, www.mannysdeli.com
The drive-in hot-dog joint Superdawg is as old-school as it gets. Orders are brought out to the car, à la Happy Days. Winking, 12-foot hot-dog figures beckon hungry passersby from the roof. And the original menu -- malts, burgers, and dogs -- hasn’t changed.
Of course, the backstory is as tasty as the grub. In 1948, Maurie and Florence Berman married and then opened a hot-dog shop inspired by superhero comics of the 1940s. The shop was located at the end of the streetcar line and across the street from a public pool, so there was a built-in customer base of families and cruising teens. The building received a bit of a neon face-lift in the late ’90s, but the 1940s charm remains. 6363 North Milwaukee Avenue, (773) 478-7800, www.superdawg.com
Original Rainbow Cone might be a hike from downtown, but it’s worth it. The family-run shop on Chicago’s South Side serves dreamy ice cream with a side of history. Since 1926, throngs of locals have waited in line for the infamous five-flavor rainbow cone, which boasts layers of chocolate, pistachio, strawberry, and Palmer House (cherry-nut) ice cream topped with orange sherbet. Now run by the granddaughter of founder Joseph Sapp, the shop emanates vintage integrity and has increased its offerings to include sundaes, floats, and draft root beer. 9233 South Western Avenue, (773) 238-7075
Putting the Lounge in Cocktail
Opened in 1907, the Green Mill Cocktail Lounge is one of the oldest jazz clubs in the country. Leased to Al Capone’s gang in the 1920s, the club became a speakeasy with a glamorous blend of jazz (Billie Holiday and Anita O’Day), gangsters, celebrities (Charlie Chaplin and Gloria Swanson), and elegantly attired ladies. During Prohibition, bootleg whiskey was brought in through a trapdoor (which still exists) near the bar.
Zebra Lounge, a tiny yet tony piano bar filled with kitschy zebra-themed memorabilia, is tucked into the shadows of stately Gold Coast brownstones. Opened the day Prohibition ended -- December 5, 1933 -- the quirky watering hole has hard-core martinis and a rollicking roster of piano standards, making it perfect for a nightcap. 1220 North State Parkway, (312) 642-5140
Worth a Visit
For a truly splendid splash, hit the art deco pool at the Intercontinental Hotel (originally the Medinah Athletic Club), a historic landmark. The grand pool -- a masterpiece of Spanish majolica tiles and Roman-style arches -- was built just before the stock-market crash of 1929. $16 a day, 505 North Michigan, (312) 944-4100, www.icchicagohotel.com
Collect your car speakers and settle in for a $9 double feature at the Cascade Drive-in (opened in 1961) in West Chicago. It’s a true Grease-era movie experience. You’ll be channeling Sandy and Danny in no time. Box office opens at seven p.m. daily, March through mid- November. 1100 East North Avenue, (630) 231-3150, www.cascadedrivein.com