Tours & Activities in Chicago

Experience Chicago’s legendary architecture from the best seat in the house: the river. Enjoy a comprehensive tour with a live fun guide as you navigate through the heart of the city covering all 3 branches of the Chicago River.

Take an exciting educational adventure aboard Tall Ship Windy with this cruise from Navy Pier in Chicago. Watch as Great Lakes history and maritime traditions come to life.

Enjoy a private two and a half hour sailing experience for up to four 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. All charters are NON-SMOKING experiences.

Set sail on the Chicago River and Lake Michigan and see the Second City by night

Celebrate Christmas Eve on a cruise on Lake Michigan aboard the Odyssey. Savor a delicious holiday 3-course plated meal served at your private table with a live onboard DJ.

Set sail on an unparalleled celebration with our Premier Plus Chicago 4th of July Dinner Cruise. Kick off the summer festivities with panoramic views of the city's unique architecture and a front row seat to the spectacular fireworks display from our glass-enclosed vessel on the Chicago River. You'll enjoy a delicious, three-course menu and specialty summer cocktails as we cruise under the city's famous skyscrapers and landmarks including DuSable Bridge, Merchandise Mart, Willis Tower, the Old Chicago Post Office, and more. Our exceptional service and masterful DJ create an exquisite atmosphere on our boat's climate-controlled interior and open-air decks. Come done and dance on the alluring Chicago River for the ultimate 4th of July celebration. Include 3-hour dinner cruise on the Chicago River Delicious plated dinner with freshly prepared entrees, salads, and desserts Spectacular views of the city skyline and local landmarks Guaranteed table for your party size

Watch the fireworks dance over Chicago's skyline during this speed boat tour

Watch the sun slowly set behind the city from the tranquil waters of Lake Michigan on this serene and romantic cruise. Toast the end of the day with a glass of wine, ice-cold beer or hand-crafted cocktail.

When in Chicago, cruising down the Chicago River is a must. Except with us, you’ll be taking in the architecture of the buildings that line the beautiful river. We provide detailed explanations of the construction and history of over 50 significant buildings, wrapping up at the end of the river. The Chicago River Cocktail Cruise allows you to experience an architecture tour with a cocktail in your hand!

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. All charters are NON-SMOKING experiences.

Set sail on a breathtaking celebration with a Premier Chicago New Year’s Eve Fireworks Dinner Cruise on Lake Michigan. Indulge in an unforgettable evening of delicious craft cocktails, plated, chef-prepared menus, top-notch service and the best views of the spectacular Chicago fireworks display. Our DJ sets the mood while you soak in the Chicago skyline from an intimate, climate-controlled interior and open-air rooftop decks. You’ll delight in awe-inspiring sights, like Adler Planetarium and Navy Pier as you ring in the new year with a magnificent celebration! Includes 21+ Only Please arrive at the boarding location at least 30 minutes before your scheduled cruise time. The tour will begin promptly.

This Wine & Cheese Cruise is a world class Chicago experience for locals and visitors. Board our famous tour boats at Michigan Avenue, and enjoy the Chicago River and Lake Michigan while tasting wine and cheese pairings. There is also a full service bar and climate controlled cabin on the vessel's lower deck. This activity does not have a narrated tour but features light music during the cruise.

Enjoy a private two and a half hour sailing experience for up to four 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. All charters are NON-SMOKING experiences.

Set sail on an unparalleled celebration with our Premier Plus Chicago 4th of July Dinner Cruise. Kick off the summer festivities with panoramic views of the city's unique architecture and a front row seat to the spectacular fireworks display from our glass-enclosed vessel on the Chicago River. You'll enjoy a delicious, three-course menu and specialty summer cocktails as we cruise under the city's famous skyscrapers and landmarks including DuSable Bridge, Merchandise Mart, Willis Tower, the Old Chicago Post Office, and more. Our exceptional service and masterful DJ create an exquisite atmosphere on our boat's climate-controlled interior and open-air decks. Come done and dance on the alluring Chicago River for the ultimate 4th of July celebration. Include 3-hour dinner cruise on the Chicago River Delicious plated dinner with freshly prepared entrees, salads, and desserts Spectacular views of the city skyline and local landmarks Guaranteed table for your party size

This Wine & Cheese Cruise is a world class Chicago experience for locals and visitors. Board our famous tour boats at Michigan Avenue, and enjoy the Chicago River and Lake Michigan while tasting wine and cheese pairings. There is also a full service bar and climate controlled cabin on the vessel's lower deck. This activity does not have a narrated tour but features light music during the cruise.

When in Chicago, cruising down the Chicago River is a must. Except with us, you’ll be taking in the architecture of the buildings that line the beautiful river. We provide detailed explanations of the construction and history of over 50 significant buildings, wrapping up at the end of the river. The Chicago River Cocktail Cruise allows you to experience an architecture tour with a cocktail in your hand!

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. All charters are NON-SMOKING experiences.

Set sail on a breathtaking celebration with a Premier Chicago New Year’s Eve Fireworks Dinner Cruise on Lake Michigan. Indulge in an unforgettable evening of delicious craft cocktails, plated, chef-prepared menus, top-notch service and the best views of the spectacular Chicago fireworks display. Our DJ sets the mood while you soak in the Chicago skyline from an intimate, climate-controlled interior and open-air rooftop decks. You’ll delight in awe-inspiring sights, like Adler Planetarium and Navy Pier as you ring in the new year with a magnificent celebration! Includes 21+ Only Please arrive at the boarding location at least 30 minutes before your scheduled cruise time. The tour will begin promptly.

This Wine & Cheese Cruise is a world class Chicago experience for locals and visitors. Board our famous tour boats at Michigan Avenue, and enjoy the Chicago River and Lake Michigan while tasting wine and cheese pairings. There is also a full service bar and climate controlled cabin on the vessel's lower deck. This activity does not have a narrated tour but features light music during the cruise.

Enjoy a private two and a half hour sailing experience for up to four 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. All charters are NON-SMOKING experiences.

Set sail on an unparalleled celebration with our Premier Plus Chicago 4th of July Dinner Cruise. Kick off the summer festivities with panoramic views of the city's unique architecture and a front row seat to the spectacular fireworks display from our glass-enclosed vessel on the Chicago River. You'll enjoy a delicious, three-course menu and specialty summer cocktails as we cruise under the city's famous skyscrapers and landmarks including DuSable Bridge, Merchandise Mart, Willis Tower, the Old Chicago Post Office, and more. Our exceptional service and masterful DJ create an exquisite atmosphere on our boat's climate-controlled interior and open-air decks. Come done and dance on the alluring Chicago River for the ultimate 4th of July celebration. Include 3-hour dinner cruise on the Chicago River Delicious plated dinner with freshly prepared entrees, salads, and desserts Spectacular views of the city skyline and local landmarks Guaranteed table for your party size

When in Chicago, cruising down the Chicago River is a must. Except with us, you’ll be taking in the architecture of the buildings that line the beautiful river. We provide detailed explanations of the construction and history of over 50 significant buildings, wrapping up at the end of the river. The Chicago River Cocktail Cruise allows you to experience an architecture tour with a cocktail in your hand!

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. All charters are NON-SMOKING experiences.

Set sail on a breathtaking celebration with a Premier Chicago New Year’s Eve Fireworks Dinner Cruise on Lake Michigan. Indulge in an unforgettable evening of delicious craft cocktails, plated, chef-prepared menus, top-notch service and the best views of the spectacular Chicago fireworks display. Our DJ sets the mood while you soak in the Chicago skyline from an intimate, climate-controlled interior and open-air rooftop decks. You’ll delight in awe-inspiring sights, like Adler Planetarium and Navy Pier as you ring in the new year with a magnificent celebration! Includes 21+ Only Please arrive at the boarding location at least 30 minutes before your scheduled cruise time. The tour will begin promptly.

This Wine & Cheese Cruise is a world class Chicago experience for locals and visitors. Board our famous tour boats at Michigan Avenue, and enjoy the Chicago River and Lake Michigan while tasting wine and cheese pairings. There is also a full service bar and climate controlled cabin on the vessel's lower deck. This activity does not have a narrated tour but features light music during the cruise.