• Exploring Millennium Park: This downtown park, carved out of the northwest corner of Grant Park, is one of the city's best spots for strolling, hanging out, and people-watching. (Bonus: It's an easy walk from downtown hotels.) While the Pritzker Music Pavilion, designed by Frank Gehry, is the highest-profile attraction, the park's two main sculptures have quickly become local favorites. Cloud Gate, by British sculptor Anish Kapoor, looks like a giant silver kidney bean; watch your reflection bend and distort as you walk around and underneath. The Crown Fountain, designed by Spanish sculptor Jaume Plensa, is framed by two giant video screens that project faces of ordinary Chicagoans. It looks a little creepy at first, but watch the kids splashing in the shallow water and you'll soon realize that this is public art at its best.
  • Bonding with the Animals at Lincoln Park Zoo: You have no excuse not to visit: Lincoln Park Zoo is open 365 days a year and—astonishingly—remains completely free, despite many recent upgrades. Occupying a prime spot of Lincoln Park close to the lakefront, the zoo is small enough to explore in an afternoon and varied enough to make you feel as though you've traveled around the world. For families, this is a don't-miss stop.
  • Listening to Music Under the Stars: Summer is prime time for live music—and often you won't have to pay a dime. The Grant Park Music Festival presents free classical concerts from June through August in Millennium Park. A few blocks south, you'll find the outdoor dance floor that's home to Chicago SummerDance, where you can learn new dance moves and swing to a variety of live acts on Thursday through Sunday nights. The summer also brings a range of large-scale music festivals—from Blues Fest to a rock-'n'-roll-themed Fourth of July concert—but the Grant Park classical concerts are considerably less crowded (and far more civilized).
  • Discovering Future Masterpieces: Chicago's vibrant contemporary art scene is divided between two different neighborhoods. The original, River North, is still home to many of the city's best-known galleries and is within walking distance from downtown hotels. The West Loop houses newer galleries—with, overall, a younger perspective—in freshly renovated lofts. You don't need to be a serious collector to browse; just bring an open mind.

Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.