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Chicago's Finest Yacht Charters, Boat Rentals and Lake and River Tours

More than 40,000 5-Star Rated Guests Chose Seas the Day Recommended Boat Charters and Tours

After meticulously reviewing hundreds of Chicago's boat charters and tours, Seas the Day Chicago stands unrivaled. Over 40,000 satisfied guests echo our excellence in providing the ultimate boating experience in the heart of the Windy City. We're not just the best, we're tried, tested, and trusted. Dive into Chicago's rich maritime culture with live availability and easy online booking. Learn more and join the thousands who've seized their day with us. Seas the Day Chicago - where every voyage is an adventure.

Discover Chicago Yacht Charters, Boat Rentals and Boat Tours

Start browsing Great Lakes yacht charters, boat rentals, Chicago river tours and more! Search by activity to begin your adventure and book online. 


Chicago’s Award Winning Architecture River Cruise From $39.00

Take in some of the Windy City’s most iconic sights on a relaxing, time-saving Chicago River architecture boat tour—pets welcome. As you cruise along multiple branches of the river, your onboard guide shares commentary on the city’s world-famous skyline, pointing out dozens of landmark buildings, including the Wrigley Building and John Hancock Building. In a single tour, you’ll enjoy sweeping riverfront views while hearing insider stories and architectural details you might otherwise miss.

Navy Pier Private Luxury Fireworks Yacht Charter From $999 $799 per Group

From Navy Pier Marina, we will cast off and motor out to Lake Michigan where we will set sail to a favorable course to enjoy the sunset on the water. Sip a beverage, enjoy the company of your crew, listen to music, relax, and take in the glittering skyline with camera ready. On warm summer nights we have the option to anchor and swim. This tour offers an unbeatable up close and personal view of the Navy Pier Fireworks Show, a once-in-a-lifetime experience!

Chicago Lake Michigan Sunset Cruise – #1 Rated From $45

Take in a truly unique view of the Windy City on an evening cruise timed perfectly with sunset. Board your open-air vessel, complete with an enclosed, climate-controlled lounge, in the heart of the Magnificent Mile and glide along the Chicago River. Then continue out onto Lake Michigan, where you’ll enjoy sweeping skyline views from the water as the city’s skyscrapers begin to glow against the evening sky.

Lake Michigan Speedboat Ride Aboard Legendary SeaDogg From $31

Race along Lake Michigan’s shoreline on an exhilarating Chicago speedboat adventure. Departing from Navy Pier, you’ll climb aboard a powerful 2,000-horsepower boat and hold on as you cruise past iconic sights like Willis Tower, Grant Park, and Buckingham Fountain. Along the way, enjoy brief pauses to hear fascinating stories about the Windy City’s history and architecture.

Day Cruise From $600.00

Set sail with Poseidon Chicago Charters for an unforgettable daytime experience on the magnificent Lake Michigan! The Chicago skyline provides a stunning backdrop to your special occasion. Whether you’re celebrating a momentous bachelor or bachelorette party, marking a milestone birthday, orchestrating a romantic engagement, hosting an intimate wedding celebration, toasting years of love on an anniversary, joyfully declaring a new chapter at a divorce party, commemorating a hard-earned graduation, capturing picture-perfect moments on a photoshoot cruise, or hosting any other unique private event, our daytime charters offer the perfect setting to create lasting memories with your cherished companions.

The Chicago River Cruise From $600.00

Embark on a captivating journey through the heart of the Windy City with a unique Chicago River cruise! Discover hidden gems and gain an entirely new perspective as you navigate the bustling waterways, where architectural marvels rise majestically along the banks. Imagine gliding past the lively Chicago Riverwalk, catching glimpses of its inviting patios and restaurants buzzing with energy and offering tempting access right from the water.

Chicago River Cruise From $350.00

Experience Chicago from a whole new perspective with a private cruise aboard a beautifully restored 1962 vintage motorboat. Glide past iconic landmarks like Centennial Fountain, Navy Pier, and the Chicago Harbor Locks, all while enjoying the peace and privacy of your own exclusive vessel. This intimate, crowd-free experience offers stunning views of the city’s skyline and architectural gems, perfect for a special outing or simply discovering the city in style.

Sea Ray 450 Believe Chicago From $975.00

At Believe Tours Charter Chicago, we offer the ultimate yachting experience on our luxurious Sea Ray 50 ft!

The yacht comes equipped with a spacious living area, full kitchen, two bathrooms, and a comfy bedroom. Our experienced team of professionals goes above and beyond to ensure you and your guests are comfortably accommodated and entertained while on board. Allow us to help you create the perfect yachting experience of a lifetime.

Private Boat Tour From $1,000.00
Join Dave for a cruise on the Chicago River in your own private vessel for up to 10 people. Learn about the Chicago skyline and how innovative architecture shaped the city and changed the world.

Ditch the herd with the microphone and the same old speech for an interesting local perspective and find out why Chicago came to be such a world class city on the water.

22 FT Private Pontoon Cruise – 2 Hours From $489.00
Enjoy cruising the beautiful Chicago River for 2 hours

The 22 ft pontoon has more space and a table for snacks and drinks. BYOB and food or allow us to cater so you have less to carry.

You are the driver. Our crew will give you or someone in your group a lesson when you arrive

Gas Powered, automatic. simple to drive.

BYOB and snacks are welcome or we will be happy to cater to you.

51′ Sea Ray Sundancer Powerboat From $1,335.00

The Yacht has a huge front of the boat that can fit the entire group plus a sun pad. The back seating area of the boat has a plenty of room and turns into a lounger. She is a two bathroom, two bedroom sailboat with a great dining and lounging area below and a large refrigerator and freezer. We also have a four person blow up raft for people to enjoy while swimming in the playpen.

57ft. Power Catamaran From $4,500.00

Step aboard Montauk, a Hamptons-inspired 57’ power catamaran designed for private charters of up to 49 guests. Perfect for any celebration, the Montauk features a full-service bar, private bathroom, bluetooth JL Audio surround sound, and an optional DJ booth. Your experience is fully private, with a USCG-licensed captain and a professional crew—including bartenders and event planners—dedicated to creating a seamless, unforgettable outing.

Chicago Vibes 440 Carver From $1,050.00

At Believe Tours Charter Chicago, we offer the ultimate yachting experience on our luxurious Sea Ray 50 ft!

The yacht comes equipped with a spacious living area, full kitchen, two bathrooms, and a comfy bedroom. Our experienced team of professionals goes above and beyond to ensure you and your guests are comfortably accommodated and entertained while on board. Allow us to help you create the perfect yachting experience of a lifetime.

Experience World-Class Architecture in Chicago by Land or by Boat

  Chicago is more than a city with tall buildings. It is a living museum of world-class architecture, bold engineering, historic neighborhoods, and unforgettable skyline views. From the Chicago River to the lakefront, from Art Deco towers to modern skyscrapers, every corner of the city tells a story. For visitors and locals looking for the…

Wendella vs. Shoreline: Chicago’s Friendly River Tour Rivalry

Wendella vs. Shoreline: Chicago’s Friendly River Tour Rivalry Chicago loves a good rivalry. Cubs vs. Sox. Deep dish vs. tavern-style. North Side vs. South Side. And on the water, one of the city’s most recognizable matchups is Wendella Tours vs. Shoreline Sightseeing. For generations of visitors and locals, both names have been part of the…

Discover the Best Chicago River Boat Cruises with Seas The Day Chicago

Chicago is a city best experienced from the water. While the skyline is stunning from the sidewalk, nothing compares to seeing the city’s legendary architecture, bridges, riverwalk, and waterfront energy from the deck of a boat. Whether you are visiting for the first time, planning a special celebration, entertaining out-of-town guests, or looking for a…

Chicago Lake Michigan Boat Tours: See the City from the Water

There is no better way to experience Chicago than from the water. With its world-famous skyline, beautiful lakefront, and lively summer atmosphere, the city was made for unforgettable Chicago Boat Tours. Whether you are visiting Chicago for the first time, planning a local day out, celebrating a special occasion, or looking for a new way…