The Hancock may not be quite as famous as the Sears Tower, but the view from the city's third-tallest building is as good as any in town. A high-speed elevator carries passengers to the observatory in 40 seconds, and on a clear day, you can see portions of the three states surrounding this corner of Illinois (Michigan, Indiana, and Wisconsin), for a radius of 40 to 50 miles. The view up the North Side is particularly dramatic, stretching from nearby Oak Street and North Avenue beaches, along the green strip of Lincoln Park, to the suburbs that trace the shoreline beyond. During your visit, you're given a handheld PDA that delivers a "Sky Tour," using audio and video to highlight features of interest across the skyline (kids get their own version). The Skywalk open-air viewing deck, surrounded on all sides by a safety screen, allows visitors to feel the rush of the wind at 1,000 feet. There's also a cafe with an adjoining kids' play area if you want to linger over a cappuccino and snack, and a complimentary concierge service. Allow 1 hour.
"Big John," as some locals call the building, also has a restaurant, the Signature Room at the 95th, and a bar, the Signature Lounge. For about the same cost as the observatory, you can take in the views with a libation in hand.