DAY 2

Once you manage to roll out of your plush bed, grab a cab head to the Pilsen neighborhood for carnitas at Don Pedro. Served family-style with red and green salsas and heaping bowls of pico de gallo and pickled peppers, they're a fiery, design-it-yourself beginning to an active day.

When you've had your fill (and lingered a bit over live mariachi tunes), kick things into gear with a sightseeing cruise. The Chicago Architecture Foundation runs several cruises daily from May through October aboard one of two 1920s luxury yachts departing from Michigan Avenue and lower Wacker Drive on the Chicago River at the Mercury Cruise Lines dock. They offer great insight into the city's signature structures. Chicago's skyline boasts styles from Beaux Arts to Art Deco and Mies van der Rohe modern. Among the more than 50 historic and architecturally significant sites you'll see on the 90-minute cruise are the Wrigley Building, the Tribune Tower and the Sears Tower. It's wise to purchase tickets in advance by calling 312-922-3432.

Sears Tower

By now, you may be craving Chi-town snack. Although it's hard to single out the "it" place for a Chicago-style hotdog, we're partial to The Wiener's Circle, a loud stand where the charred sausages—topped with pickles, tomatoes, raw onion, mustard and relish—snap between your teeth. In search of something more gussied up? You can get a bite of something more gourmet at Hot Doug's, a stand known for its adventurous cased meats and duck fat-crisped fries.

On the other hand, you need not feel wedded to this. Puerto Rican and Asian-flavored Belly Shack, Bill Kim's industrial-edged, counter-service storefront, embodies the spirit of Chicago's modern-day cuisine. The garlicky chimichurri-topped tostones and Asian meatball sandwich are tops, but don't overlook the soft-serve ice cream, which interesting toppings—like huckleberry-lime zest and bacon-chocolate chip—courtesy of HotChocolate's Mindy Segal.

When your tummy is ready to burst, make fast tracks to Lincoln Park Zoo to work off some calories. This primal pit-stop, while not nearly as large as southwest suburban Brookfield Zoo, has serious appeal—not to mention complimentary admission and a flamingo habitat, sea lion pool and booming primate house. Once you've seen all the exhibits, take a stroll along the park's winding paths to the Lincoln Park Conservatory, with its breathtaking canopy of tropical palms and ancient ferns.

Cibo Matto

Soon, you'll be ready for a memorable dinner. At Moto, scientist-meets-chef Homaro Cantu is just the man to take out-of-town guests on a staggering culinary journey. His post-modern cuisine, presented in five-, ten- and eighteen-course tasting menus, may include nitro sushi and freeze-dried macaroni with quail. For something more down-to-earth, opt for Cibo Matto in theWit, where mk-vet Todd Stein rocks out plates of seasonally garnished burrata—perhaps with smoked bacon and onion marmalade—and unbeatable bucatini carbonara with a cracked duck egg.

Crown your evening with comedy at The Second City. This longtime improvisational comedy troupe, boasting alumnae like John Belushi, Dan Aykroyd, Bill Murray, Chris Farley, Tina Fey, Bonnie Hunt, Dan Castellaneta, Steve Carrell and Stephen Colbert among many others, features original comedy revues and student productions. You never know, you could end up watching the next big comedy star. Alternatively, you could see a performance by the Improvised Shakespeare Company, which cranks out gut-busting couplets to rave reviews.