Ship to shore. Chicago gave birth to the world's first skyscraper in the late 19th century and has since become a living museum of notable buildings. Learn more aboard a Chicago's First Lady Cruise, run by the Chicago Architecture Foundation. The 90-minute tours ply the city's eponymous river, highlighting landmarks such as the Wrigley Building and the Tribune Tower ($28 weekdays, $32 weekends). cruisechicago.com
Upper crust. Deep-dish pizza was invented during World War II at Pizzeria Uno, either by restaurant founder Ike Sewell or, some claim, his employee, Rudy Malnati. The original Uno still exists, at 29 East Ohio, but Lou Malnati's, launched by Rudy's son in 1971, is perhaps a more authentically Chicago experience. The outpost nearest McCormick Place is at 805 S. State St. loumalnatis.com
High times. Chicago's newest and scariest attraction is The Ledge at Willis Tower, formerly called the Sears Tower but still the tallest skyscraper in North America. Glass compartments jut out from the 103rd-floor Skydeck, allowing unobstructed views of the city from 1,353 feet. Cost: $15. theskydeck.com
The Publican, at 837 W. Fulton Market, is a new "beer-focused" restaurant winning rave reviews for its simple farmhouse fare. Chicagoist.com recommends the pork rinds: "Chef Brian Huston somehow manages to deep-fry the rinds until they're lighter than popcorn, then drizzles them with cider vinegar." thepublicanrestaurant.com
Beyond the Miracle Mile. Shop the less-beaten path. From the Loop downtown, take the Brown Line train ($2.25) north to Armitage Avenue for local boutiques, including Cynthia Rowley (pictured).
For more, visit Chicagoist.com, a great Windy City blog, and the Chicago Convention & Tourism Bureau (choosechicago.com).