Photograph courtesy Christopher Beauchamp/Photoshelter
Chicago may be the third-largest city in America, but it’s easily navigable even with kids in tow. Make The Loop—the city’s historic core—your base. Children dig Kimpton’s Hotel Allegro, with its colorful decor and free afternoon hot chocolate (parents will like the gratis wine). By Lake Michigan, on the neighborhood’s eastern edge, Millennium Park offers free concerts in the Frank Gehry-designed Jay Pritzker Pavilion, unbeatable photo ops at Anish Kapoor’s steel sculpture Cloud Gate, and wet romps in the Crown Fountain, an interactive reflecting pool/video tower. The city is filled with great architecture (the skyscraper was born here—fancy that) and public artworks (by Picasso, Calder, Miró, and Chagall) a tween can appreciate. And if you want to spoil the kids more with the city’s embarrassment of cultural riches, spend time south of the park at the Art Institute, the Shedd Aquarium, and the Field Museum. As for eats, feed them Chicago’s finest: a charred dog at the famed Wieners Circle (near the Lincoln Park Zoo) or deep dish from the flagship Gino’s East, off Michigan Avenue.