Situated on Lake Michigan, the windy city is known for its fantastic shoreline, amazing architecture, and legendary musical spirit.
Sights to see: Skyscrapers were invented in this "city of steel"; the best way to learn about their history is by floating in a boat down the Chicago River. The Chicago Architecture Foundation offers tours that are educational for adults -- and entertaining for kids ($26; April through November 18). One of the city's top attractions, the Museum of Science and Industry, features a U-505 submarine exhibit (the only German sub captured by the U.S. Navy in World War II) and robots that make and assemble customized toys ($11 for adults, $7 for children 3 to 11; msichicago.org). Window shop along the Magnificent Mile or head to the Lincoln Park Zoo, free and open every day of the year. From November to March, rent skates for $7 and glide around the McCormick Tribune Plaza and ice rink in downtown Millennium Park, the city's new architectural jewel, where works of art and sculpture by renowned artists, including architect Frank Gehry, are on display.
Family fun: Chicago is famed for its music clubs. One of the best, Joe Segal's Jazz Showcase (jazzshowcase.com), has a family program every Sunday at 4 p.m. For more local flavor, try the Gospel Brunch at the House of Blues, featuring an unlimited buffet and enthusiastic performers (hob.com).
Off the expense account: Just a few blocks from Michigan Avenue, the Red Roof Inn Chicago Downtown has budget-friendly rooms in the heart of the action starting at $119. Info: 877-244-2246