Top 10 Sightseeing Cruises in Chicago

Destination: Chicago.
Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline. Make the experience your own. The flexibility of a private charter allows customization of virtually any aspect of the sailing adventure from guest list to music selection to sailing route. Three departure times offered daily. This experience is not meant to be an in-depth guided tour; however, our captain is always happy to point out interesting sights with anecdotes and historical information. Just ask you captain. Looking for a sunset sail, see our other product listing "Come Sailing with us at Navy Pier - Sunset Sail on Lake Michigan". Looking to watch the Navy Pier Fireworks from a private sailing charter, see our other product listing "Come Sailing with us at Navy Pier - Saturday Fireworks Sail". All charters are NON-SMOKING experiences.
Known For: Chicago Private Sightseeing Tours, Chicago Likely to Sell Out, Chicago Day Cruises, Chicago Sailing, Chicago Water Tours, Chicago Sightseeing Cruises, Chicago Full-day Tours, Chicago Likely To Sell Out.
Duration: Around 2 hours.

Destination: Chicago.
Travel on a piece of history, learning Chicago fire history as well as Architecture! We travel through the Chicago River seeing the sights. Perfect for Fire enthusiasts, families and everyone in between! Our flagship vessel is a retired Chicago fire boat, the Fred A Busse, Engine 41, which served Chicago from 1937 to 1981. Firefighter patches from around the world and memorabilia from Engine 41's time in service, adorn the walls inside the cabin.
Known For: Chicago Water Tours, Chicago Seasonal, Chicago Sightseeing Cruises, Chicago Day Cruises, Chicago Historical Tours.
Duration: Around 1 hour and a half.

Destination: Chicago.
Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline. Make the experience your own. The flexibility of a private charter allows customization of virtually any aspect of the sailing adventure from guest list to music selection to sailing route. This experience is not meant to be an in-depth guided tour; however, our captain is always happy to point out interesting sights with anecdotes and historical information. Just ask you captain. Looking for daytime sailing, see our other product listing "Come Sailing with us at Navy Pier - Sail Beautiful Lake Michigan". Looking to watch the Navy Pier Fireworks from a private sailing charter, see our other product listing "Come Sailing with us at Navy Pier - Saturday Fireworks Sail". All charters are NON-SMOKING experiences.
Known For: Chicago Likely to Sell Out, Chicago Day Cruises, Chicago Sunset Cruises, Chicago Likely To Sell Out, Chicago Sailing, Chicago Sightseeing Cruises, Chicago Private Sightseeing Tours, Chicago Water Tours, Chicago Excellent Quality.
Duration: Around 2 hours.

Destination: Chicago.
Travel on a piece of history, learning Chicago fire history as well as Architecture! We travel on Lake Michigan and through the Chicago River seeing the sights. Perfect for Fire enthusiasts, families and everyone in between! Our flagship vessel is a retired Chicago fire boat, the Fred A Busse, Engine 41, which served Chicago from 1937 to 1981. Firefighter patches from around the world and memorabilia from Engine 41's time in service, adorn the walls inside the cabin.
Known For: Chicago Christmas, Chicago Day Cruises, Chicago Water Tours, Chicago Sightseeing Cruises, Chicago Excellent Quality, Chicago New Product, Chicago National Holidays, Chicago Historical Tours, Chicago Best Conversion, Chicago Architecture Tours.
Duration: Around 2 hours.

Destination: Chicago.
Marvel at the magnificent architecture on the Chicago River with expert tour guides! All ages welcome. Each architecture river tour is narrated by a professional guide which leads passengers down the Chicago River to discover the city’s most renowned landmarks. In addition to historical insight on well known structures such as the Civic Opera House, Trump Tower & the Merchandise Mart, passengers will also get a chance to learn about current and upcoming developments. This Chicago River Cruise is the only cruise that navigates the three primary branches of the river including the main branch to Navy Pier, the north branch to Goose Island, and the south branch to Chinatown. It is also the cruise closest to Skydeck, has the least expensive parking, and is great for those coming from the suburbs due to its location off Interstate 290.
Known For: Chicago Day Cruises, Chicago Top Product, Chicago Night Cruises, Chicago Historical Tours, Chicago Sightseeing Cruises, Chicago Architecture Tours, Chicago Sunset Cruises, Chicago City Tours, Chicago Water Tours, Chicago Excellent Quality.
Duration: Around 1 hour and a half.

Destination: Chicago.
Experience the stunning beauty of Chicago on a captivating cruise along the historic Chicago River. This architectural tour takes you down the main branch of the river, up the north branch to the East Bank Club, and then south past the iconic Willis Tower (Sears Tower) to the historic Old Post Office Building. Marvel at the magnificent city skyline as you pass by over 40 notable buildings, including: John Hancock Center: An iconic skyscraper that defines the Chicago skyline. Wrigley Building: Known for its distinctive white facade and clock tower. As you sail, an expert architecture guide will provide fascinating insights into the distinctive designs and history of these architectural marvels. Whether you're a local or visiting for the first time, this tour offers a unique perspective on one of the world's most beautiful cities. Sit back, relax, and let the architectural wonders of Chicago unfold before your eyes.
Known For: Chicago City Tours, Chicago Best Conversion, Chicago Sightseeing Cruises, Chicago Excellent Quality, Chicago Day Cruises, Chicago Water Tours, Chicago Architecture Tours, Chicago Top Product.
Duration: Around 1 hour.

Destination: Chicago.
Enjoy Chicago’s famous sights and fabulous views on this award-winning small-group sightseeing tour of the city. On this tour, you will travel through Chicago with an expert guide in a comfortable minibus, enjoy world renowned architecture including the world's first skyscrapers, Museum Campus (for the BEST skyline view in town), Millennium Park (Home of "The Bean"), Buckingham Fountain, The Magnificent Mile, Lincoln Park, Chicago River, The Gold Coast, Lake Shore Drive and more! You also have the option to upgrade to include THE most popular Architecture River Cruise in Chicago! For good reason, our partner Shoreline Sightseeing, has been the most booked tour on TripAdvisor for the last 5 years! And yes, there is a bar on the boat. The combo option will end at Shoreline Sightseeings Navy Pier location, after you finish the boat tour you will be walking distance from many other attractions in the city! **there will be no provided transportation after your boat tour**
Known For: Chicago Sightseeing Cruises, Chicago Architecture Tours, Chicago Bus Tours, Chicago Cultural Tours, Chicago Water Tours, Chicago Day Cruises, Chicago Excellent Quality, Chicago City Tours.

Destination: Chicago.
Be inspired by the captivating, visual art that is Chicago’s legendary architecture, and the exceptional architects who created this ever-changing, dynamic legacy for all to enjoy and admire. This comprehensive 90 minute tour will navigate through the heart of the city on all three branches of the Chicago River while your professionally-trained architectural guide tells the story of more than 130 years of innovation in design, style and technique and why it is important today. The Chicago River Architecture Tour is the most authentic and encompassing Chicago experience the city has to offer.
Known For: Chicago City Tours, Chicago Best Conversion, Chicago Likely to Sell Out, Chicago Top Product, Chicago Day Cruises, Chicago Night Tours, Chicago Likely To Sell Out, Chicago Sightseeing Cruises, Chicago Water Tours, Chicago Excellent Quality.
Duration: Around 1 hour and a half.

Destination: Chicago.
An authentic Chicago tradition since 1935, this is the tour that started it all. This unique excursion tells the story of more than 200 years of fascinating social, cultural and political history, and explores more than a century of groundbreaking architecture. The journey begins with an up-close perspective of Chicago's internationally-known architecture as seen from the Chicago River. Then venture through the Chicago Lock on to the calm, cool waters of Lake Michigan for expansive views of Chicago's extraordinary 26-mile skyline. Take the selfie of a lifetime on this inspirational experience!
Known For: Chicago Architecture Tours, Chicago City Tours, Chicago Best Conversion, Chicago Likely to Sell Out, Chicago Top Product, Chicago Day Cruises, Chicago Likely To Sell Out, Chicago Sightseeing Cruises, Chicago Water Tours, Chicago Excellent Quality.
Duration: Around 1 hour and a half.

Destination: Chicago.
Experience Chicago's legendary architecture and the exceptional architects who created this ever-changing legacy for all to admire. This family-friendly introduction to the Windy City's rich history and architectural heritage features highlights from Wendella's full-length architecture tours. Hop aboard our world class vessels as our local authentic tour guides showcase our amazing city.
Known For: Chicago Architecture Tours, Chicago City Tours, Chicago Best Conversion, Chicago Likely to Sell Out, Chicago Top Product, Chicago Day Cruises, Chicago Likely To Sell Out, Chicago Sightseeing Cruises, Chicago Water Tours, Chicago Excellent Quality.
Duration: Around 45 minutes.