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- Best Year-Round: Chicago River Architecture Cruise – Buy Tickets at Viator "Learn about world-famous architects, including Mies van der Rohe, Helmut Jahn and the Skidmore, Owings and Merrill firm."
- Best Night Tour: Chicago Fireworks Architecture Cruise – Buy Tickets at Viator "Take in the magical fireworks show while learning about the architecture from the perfect vantage point.."
- Best Boat Combo: Architecture Cruise and Speedboat Tour – Buy Tickets at Viator "The tour departs from the Navy Pier, so allow some time to explore the shops and sights."
- Best Land and Water: Chicago City Tour with Optional River Cruise – Buy Tickets at Viator "Learn about the role the river has played in the city’s development and how it structures the skyline.."
- Best Extended Tour: Chicago River Architectural Tour – Buy Tickets at Viator "Arrive early to grab a seat on the upper deck because the trip is very popular and the boat can fill up."
- Best All-In-One: Viator VIP Willis Tower Skydeck, Trolley Tour & River Cruise – Buy Tickets at Viator "By the end of the day, you’ll be an expert. Pack some snacks and a lunch – the tour lasts six hours."
- Best Short Tour: Lake Michigan Sightseeing Cruise – Buy Tickets at Viator "The 40-minute cruise gives you some fantastic photo opportunities of the city skyline."
Best Year-Round: Chicago River Architecture Cruise
For a fantastic tour at an affordable price that runs year-round (instead of only the summer months), the 75-minute, “Chicago River Architecture Cruise” departs from the bustling Navy Pier or Michigan Ave and offers an educational experience. Learn about world-famous architects, including Mies van der Rohe, Helmut Jahn and the Skidmore, Owings and Merrill firm. You'll also see more than 40 buildings, including the John Hancock Center, the Wrigley Building and the Aon Center. Be aware that some boats are one deck and some are two. Viator members also noted that the company’s customer service was outstanding and they handled special requests and changes easily.
Best Night Tour: Chicago Fireworks Architecture Cruise
During the summer months on Wednesday and Saturday nights, The Navy Pier puts on an impressive display of fireworks that illuminate the city skyline. Take in the show while learning about the architecture on the “Architecture Fireworks Cruise,” a 90-minute narrated boat ride on the Chicago River. During the tour, guides will explain the importance of the balloon-frame construction that changed how homes were built, and how the Great Fire shaped history. The boat passes by 40 iconic buildings, such as the Aon Center, the John Hancock Center, the Willis Tower (Sears Tower), the Wrigley Building and the IBM Building.
Best Boat Combo: Architecture Cruise and Speedboat Tour
If you want to combine action and adventure with historical education, consider booking the Architecture Cruise and Speedboat Tour. The 75-minute river and lake cruise begins with a laid-back journey up the river to view landmarks, including the Willis Tower and the Tribune Tower, as an informative guide shares fascinating stories about the history of these icons. After that, board a speedboat for a thrilling ride zipping along the shoreline of Lake Michigan past Grant Park (home to Buckingham Fountain), the Chicago Harbor and the Museum Campus. The tour departs from the Navy Pier, which is an attraction in itself and home to Chicago’s famous Centennial Wheel – so allow some time to explore the shops and sights.
Best Land and Water: Chicago City Tour with Optional River Cruise
If you prefer a smaller group size, the Chicago City Tour combines sightseeing in an air-conditioned bus that holds 12 people or less with a peaceful boat ride (for an additional charge). The tour begins with a narrated, two-hour ride around the city with a chance to get out and explore a few stops, including the 1888 skyscraper called The Rookery, which is known for its Frank Lloyd Wright-designed lobby. Next up is a 75-minute cruise on an open-top boat to delve even deeper into the city’s famous architecture and to learn about the role the river has played in the city’s development. Transportation from most area hotels is provided but is not round-trip.
Best Extended Tour: Chicago River Architectural Tour
For an extended version of an architecture cruise at a reasonable price, the “Chicago River Architectural Tour” runs a full 90 minutes – and has a bar on board to boot. Entertaining and educational guides narrate the journey as the boat passes more than 50 landmarks and architectural gems, keeping an eye out for gargoyles and icons from the Neoclassical period to the Art Deco era. The tour runs four times daily from April through November and departs from the Lofts at River East (Odgen Slip). Non-alcoholic refreshments and cookies are served, but beer and wine are additional. Viator members recommend arriving early to grab a seat on the upper deck because the trip is very popular and the boat can fill up.
Best All-In-One: Viator VIP Willis Tower Skydeck, Trolley Tour & River Cruise
If you’re willing to splurge a bit for a jam-packed tour, the Viator VIP tour well let you experience the architecture from every angle. First, explore the 103rd floor of Willis (Sears) Tower, and be granted early access to the Skydeck to see the glass-enclosed balconies (and floors) without the crowds. Next up is a two-hour narrated trolley tour past Grant Park, the John Hancock Center, the Wrigley Building and other landmarks. Finish off the day with a 75-minute cruise of the Chicago River and admire the skyline from the water as you learn even more fascinating information about the architecture. By the end of the day, you’ll be an expert. Pack some snacks and a lunch – the tour lasts six hours.
Best Short Tour: Lake Michigan Sightseeing Cruise
If you’re strapped on time and want a quick taste of some of Chicago’s attractions, as well as an overview of the architecture, the Lake Michigan Sightseeing Cruise is an excellent, budget-friendly option. The 40-minute cruise gives you some fantastic photo opportunities of the city skyline as you listen to commentary about the history of Chicago and major skyscrapers such as the John Hancock Center and Willis Tower. A bar is available on board for adult beverages, but it is suggested to bring your own lunch. The cruise leaves every hour from the Navy Pier's Dock Street but does not operate in the winter. Viator members felt that although a short cruise, it was a good value overall.