Top Chicago Sunset Cruises

Our Chicago Signature Dinner Cruise is an unforgettable way to experience the city from the water. Spend your evening on Lake Michigan with dining, picturesque views, dancing, DJ entertainment, and an assortment of games. While onboard, you’ll enjoy our chef-prepared dinner buffet, a fully stocked bar, and incredible views of Chicago’s skyline and attractions from our climate-controlled interior and open-air rooftop decks. Whether for a romantic dinner for two or for a special evening with friends and family, our dinner cruises are perfect for any occasion! Includes - 2 - 3-hour dinner cruise on Lake Michigan - Chef-prepared buffet-style dining - Spectacular views of the Chicago skyline including the Willis Tower and Adler Planetarium - DJ curated music - Guaranteed table for your party size - Complimentary coffee, hot tea, and iced tea Extras & Upgrades: - Creative cocktails, wine, and beer are available for purchase from our fully stocked bar

Experience one of the world’s most beautiful cities on a cruise down the historic Chicago River. On this architecture cruise, head down the main branch of the Chicago River, up the north branch to the East Bank Club, and then south past Willis Tower (Sears Tower) to the old Post Office Building. Take in magnificent city skyline views as you see more than 40 notable buildings, including the John Hancock Center and the Wrigley Building, and learn about their distinctive architecture from your onboard guide, an expert in architecture.

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.

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.  All charters are NON-SMOKING experiences.

Our Chicago Signature Lunch Cruise is an unforgettable way to experience the city from the water. Spend your afternoon on Lake Michigan with dining, picturesque views, DJ entertainment, and an assortment of games. While onboard, you’ll enjoy our chef-prepared lunch buffet, a fully stocked bar, and incredible views of Chicago’s skyline and attractions from our climate-controlled interior and open-air rooftop decks. Whether for a scenic lunch for two or for an unforgettable afternoon with friends and family, our Lunch Cruises are perfect for any occasion and serve as the best way to see Chicago from the water! 

Admire all of Chicago's fabulous lakefront sights and attractions on this Lake Michigan boat tour. Cruise along Lake Michigan and take in amazing views of the city’s famous skyscrapers from a great vantage point. Feel free to bring a lunch and enjoy drinks from the onboard bar as you relax on this sightseeing cruise.

Our Signature Chicago 4th of July Fireworks Dinner Cruise is the ultimate way to kick off summer's biggest celebration. The spectacular Chicago fireworks will captivate you as you enjoy the show from your front row seats on the water. Unparalleled festivities are in store this 4th of with dining, dancing, and magnificent skyline views on Lake Michigan for a casual evening out. Enjoy a delicious, chef-prepared buffet and gorgeous views of Chicago's spectacular architecture while soaking in the beautiful summer weather. You'll marvel at famed city landmarks, such as the Willis Tower, and Adler Planetarium, from our climate-controlled interior and open-air roof decks. We keep the spirits flowing with a fully stocked bar, games, and lively music from our DJ. Set sail on an unforgettable 4th of July celebration! Includes Must be 21 or older with valid ID 3-hour dinner cruise on Lake Michigan Delicious dinner buffet with freshly prepared entrees, salads, and desserts

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!

Leave the hustle and bustle behind! Explore Chicago's shores with a leisurely trip around Lake Michigan. Take in the world-famous skyline, enjoy spectacular views, and discover the Windy City from the water. Windy is the Official Ship for the City of Chicago. At 148 feet long, she is one of only a few 4 masted Schooners built in the United States. You will enjoy a relaxing sail around aboard a truly historic vessel. Select from Pirates and Maritime Stories Sail at 1pm, Skyline/Architectural Theme at 3pm and 5pm, and Skyline Sunset Sail at 7pm. This sail is approximately 75 minutes. The ship leaves promptly at the scheduled time, please allow for time to park, off the pier if necessary.

Welcome to Chicago River Boat Architecture Tours! We’re proud to present you with an in-depth, expert architectural-based river boat tour that delves into one of the most remarkable American cities today. Known for unique, daring, and historical architectural pursuits, it’s hard to cover all of the design and building treasures that make up the Windy City today. If you’re ready to learning more about the designs, people, and innovations behind these creations, throw on your captains hat and get ready to cruise along the Chicago River and see what architects from around the world travel to see in Chicago. Tour departures from 465 N. McClurg Ct.

Experience the best of Chicago with a Premier Dinner Cruise and spend your evening on Lake Michigan with dining, picturesque views, DJ entertainment, and dancing. While onboard, you’ll enjoy our chef-prepared plated menus, creative cocktails, distinctive service, and breathtaking views of Chicago’s skyline and attractions from our climate-controlled interior and open-air rooftop decks. Whether for a romantic dinner for two or for a special evening with friends and family, our dinner cruises are the perfect way to elevate any occasion and see Chicago from the water! Includes - 3-course, chef-plated menu - Spectacular views of the Chicago skyline including the Willis Tower - and Adler Planetarium - DJ-curated music - Guaranteed table for your party size - Complimentary coffee, hot tea, and iced tea Extras & Upgrades: - Creative cocktails, wine, and beer are available for purchase from our fully stocked bar

The Chicago Architecture Center River Cruise aboard Chicago's First Lady has long been the gold standard among all Chicago tour experiences, and is the only Chicago architecture boat tour led by highly trained expert docents. On this 90-minute cruise, you will enjoy an overview of historic and modern architectural styles including stories about the people who designed and built Chicago. No visit to Chicago is complete without experiencing this award winning tour, so accept no substitutes.