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.

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!

A family-friendly introduction to Chicago's magnificent architecture

Enjoy sailing the waters of Lake Michigan with this dinner cruise. You'll enjoy a delicious buffet dinner on board the ship – an unforgettable experience!

Skip the ticket line for Chicago’s only architecture cruise on both Lake Michigan and the Chicago River. Learn about Chicago's internationally-known architecture from expert local guides as you discover the city from riverfront to shoreline.

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.

Marvel at Chicago's iconic architecture from the water

Cruise down the Chicago River and see the city’s most spectacular landmarks on a boat cruise with live, family-friendly commentary and a full-service bar on board.

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.

See the Chicago skyline from Lake Michigan and enjoy a guided tour of the city

Cruise along the Chicago River on a 60- or 75-minute tour, and discover hidden architectural gems among the city’s renowned landmarks. Led by a docent providing live narration, the tour passes more than 40 structures and sails under historic bridges.

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.

USA Today Readers' Choice 2021 Awards #1 boat tour in North America!

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!

Take America's most popular river cruise and see Chicago's epic skyline

Experience a Chicago River cruise partnered with the world-famous Chicago Architecture Center, featuring live English-speaking certified docents and pre-recorded multilingual commentary.

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.

Enjoy a three-course dinner cruise with a Chicago backdrop

Enjoy views of Chicago's riverfront architecture as you cruise along the Chicago River. Admire the scenery from the ship's glass-enclosed dining area. Choose between a lunch, dinner, or weekend brunch.

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.

Who let the dogs out? Cruise along the water on the cutest boat trip in Chicago!

Savor an elegant afternoon or dinner on Lake Michigan. You'll delight in in awe-inspiring sights. like Willis Tower, Adler Planetarium, Navy Pier and more.

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.

Indulge in the ultimate Chicago experience with a Premier Brunch Cruise