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. Or, for a completely different — though no less fantastic — route, sleep in and later snag a Chicago original, a plantain-cradled jibarito sandwich from Borinquen, which opens daily around 11 a.m.
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.
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, or Franks 'N' Dogs, a chef-like take on the age-old sausage.
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.
Then again, you'd be wise to try scoops from Jessica Oloroso's inventive Black Dog Gelato (the goat cheese-cashew caramel is killer).
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. Nearby, there's also the secret-feeling Alfred Caldwell Lilly Pool at the southeast corner of Fullerton Parkway and Cannon Drive. A historic, hardly frequented landmark, it's marked by a river and indigenous, non-invasive prairie, woodland and aquatic plants.
Soon, you'll be ready for a memorable dinner. With some advance planning, grab a table at Girl & the Goat, where Stephanie Izard plates inventive flavors for scenesters.
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.
* City Hall and Sears Tower images by the Chicago Convention and Tourism Bureau.