Cruising the waterways since 1939, you can take your pick of two watery options with Shoreline Sightseeing. Its 60-minute architecture cruise departs from Navy Pier and travels along the Chicago River, taking in 40 celebrated buildings.
The 30-minute Skyline Boat Tour on Lake Michigan showcases Chicago from a different vantage point: You'll catch an unobstructed view of Navy Pier, the Shedd Aquarium and Buckingham Fountain. (There's also a 90-minute combo package.)
Tours run April 1 through late November. The Skyline tour costs $12 adults, $11 seniors, $6 children under 12. The Architecture cruise costs $24 adults, $21 seniors and $11 children on weekends and holidays; it costs $22 adults, $19 seniors and $11 children on weekdays.