Three Sides of Chicago
America's third-largest city is really a cluster of small towns — dozens of neighborhoods, each with its own vibe and history: Eastern European, Asian, Latino, hipster. This is the real Chicago, and it's easy to master — just take the transit authority's L and Metra systems. Base yourself downtown, where the train lines converge (and the good hotels are), and use the L to explore. Stay at the newly refurbished Chicago Athletic Association ($289 a night), a 250-foot Gothic tower that once housed the city's most exclusive gentleman's club, or The Freehand ($159 a night), which has one of the city's hottest bars, the Broken Shaker, and the best coffee in town, at Café Integral.
The Red Line to Uptown
In the early 20th century, Uptown was Chicago's most fashionable enclave, home to jewelers, furriers, and swinging ballrooms. It's in the midst of a renaissance now, a product of its classic architecture and proximity to Lake Michigan. Start in Uptown's Little Saigon, along Argyle Street. Line up for the pho at Tank Noodle; or call ahead to Sun Wah BBQ to order its famous Peking duck, which is carved tableside. Next, walk down Broadway to Bar on Buena and navigate through 100-plus beers from around the world and a deep list of whiskeys. Check ahead for rock shows at the historic Aragon Ballroom or Riviera Theatre. Then late night, relive the days when mobsters, screen stars, and big bands mingled at the Green Mill, the jazz club that Al Capone once called home.
The Green Line to Fulton Market
Many people have heard of the thriving West Loop restaurant and nightlife scene. But for locals, the real excitement has moved north to the Fulton Market District, where meatpacking trucks, street art, and ethnic eats come together. The craft-beer behemoth Goose Island Beer Co. recently opened a taproom that offers pints off a rotating list as well as tours of the facility. (Tours often sell out, so book in advance.) South America meets the Midwest at La Sirena Clandestina, whose chef, John Manion, serves up flaky empanadas, superfresh ceviches, and other Brazilian specialties. End the day at The Aviary, a swank lounge whose mad scientist bartenders take cocktails to the outer limits.
The Blue Line to Logan Square
Scandinavians, Germans, Jews, and Poles have called Logan Square home over the years, as many Latinos, artists, and hipsters do today. Grab brunch at Longman & Eagle, a Michelin-starred, no-reservations spot (try the wild boar sloppy joe). Rent a ride-share Divvy bike from the docking station at Kedzie and Milwaukee avenues, and pedal down to The 606 — a 2.7-mile paved trail through Bucktown and Humboldt Park — to catch great cityscapes as well as peeks into private homes and yards. Head back to Logan Square for dinner at Fat Rice, where chef Abraham Conlon cooks Macau-inspired fare — think Portuguese country sausage and braised sweet-and-sour pork belly. Afterward, it's off to Rosa's Lounge for live blues in a nontouristy setting, or East Room, a hipster hang with $3 whiskey shots and a soundtrack of old-school hip-hop and indie rock.
Before you book a flight to O'Hare, see if you can fly to Midway Airport instead. It's closer to downtown and quicker and easier to navigate.