Sightseeing Cruises in Chicago

This Chicago architecture boat tour by Wendella showcases over 50 architectural landmarks like Marina City and Willis Tower in 45- or 90-minute options. Enjoy narrated skyline views from open-air decks or climate-controlled interiors. Each cruise blends history, design, and unforgettable riverfront perspectives. Details

Join the Shoreline Architecture River Cruise from Michigan Avenue and witness the city’s incredible architecture and engineering marvels from the Chicago River! Cruise past over 40 iconic buildings, from the majestic John Hancock Center to the historic Wrigley Building, as your expert guide shares the history of the buildings, their architects and engineers. Details

Step aboard the Shoreline Architecture River Cruise from Navy Pier and discover the magic of the Windy City’s architectural wonders! Glide past over 40 iconic buildings, from the majestic John Hancock Center to the historic Wrigley Building, as your expert guide provides detailed descriptions. Kids age 2 and under are free, and the tour is dog-friendly, too! Details

Sail with your pup on the 90-minute, dog-friendly Canine Cruise through the Chicago River and Lake Michigan. Take in skyline views, live architectural commentary, and thoughtful amenities for both dogs and their humans. It's one of the most unique and pet-friendly things to do in Chicago. Details

Hop aboard the Chicago fireworks cruise on Lake Michigan and watch the night sky light up in 3D. Departing from the Chicago Riverwalk, take in the panoramic skyline views from the open-air deck with lively narration on the way to the Harbor Lock. Then, enjoy a spectacular fireworks show enhanced with complimentary 3D glasses and synchronized music. Details

Take in sweeping views of Chicago’s skyline from the water on the Chicago by Night Cruise. As you glide along the Chicago River and the Lake Michigan shoreline, a knowledgeable guide shares insights into the city’s architecture, history, and cultural landmarks. Watch as the skyline lights up at dusk, offering a striking and memorable perspective of the city. Details

Indulge in a premier Chicago dinner cruise aboard Odyssey Lake Michigan. Departing from Navy Pier, pass by iconic landmarks such as Willis Tower, Adler Planetarium, and more. Whether celebrating a special occasion or simply looking for a unique dining experience, this dinner cruise in Chicago offers an unforgettable evening of elegance and fine dining. Details

Explore Chicago’s skyline and landmarks on a 90-minute guided river and lake cruise aboard the First Lady. Enjoy expert commentary on architectural icons like Willis Tower, Tribune Tower, and the Wrigley Building. This family-friendly cruise offers stunning views and insights into the city’s rich history and design legacy. Details

Wendella's Chicago Lake and River Architecture Tour offers expert narration and skyline views from both the river and Lake Michigan. Cruise past more than 50 landmarks along the river, then pass through the Chicago Lock into Lake Michigan for panoramic views stretching from Navy Pier to Grant Park. Details

Experience the breathtaking Chicago Skyline on a 45-minute Lake Michigan cruise departing from Navy Pier. Enjoy stunning views of the city’s iconic landmarks and skyscrapers such as The Chicago Harbor Lighthouse and Willis Tower, and informative pre-recorded commentary about the history of Chicago’s famous buildings. Don't forget your camera! Details

Set sail on a Chicago lunch cruise for a casual day out on Lake Michigan aboard the Spirit of Chicago. Departing from the iconic Navy Pier, the cruise will pass by iconic landmarks such as the Willis Tower and Adler Planetarium. Feast on a delectable chef-prepared lunch buffet while enjoying stunning views of the Chicago skyline and onboard entertainment. Details