Book early, as these tend to sellout! you are free to move about the ship, while the music plays, everywhere.... More

Discover the fascinating history of Chicago from a whole new perspective — on the water! This 120-minute Guided History Tour along the Chicago River brings the city’s past to life through captivating stories, iconic landmarks,... More

A private sailing charter on Lake Michigan offers a serene escape with stunning skyline views of Chicago. Departing from Montrose Harbor, enjoy a relaxed atmosphere ideal for families, couples, or casual groups looking for a break... More

Get ready for the most complete adventure the city has to offer—an immersive Full Day Chicago Food Tour and Walking Tour that blends Chicago’s legendary flavors with its most iconic landmarks. Savor Chicago Pizza, Hot Dogs, It... More

Don’t miss Chicago’s famous sights and fabulous views on this award-winning private sightseeing tour of the city. Travel through Chicago with an expert guide on a comfortable minibus, stopping at iconic locations like early sk... More

See Chicago the Island Party Way. Our floating Tiki Bar offers you the opportunity to take in all the sights and sounds as you relax and enjoy a beverage. Have questions about the buildings you'll see along the river? Our helpful ... More

Kick off your Sunday the right way—with mimosas, Bloody Marys , and unbeatable views of Chicago’s stunning skyline aboard Enchantment, our flagship vessel. This ticketed cruise is the perfect blend of relaxation and celebratio... More

Celebrate the magic of the season on the water with a Christmas Eve Premier Dinner Cruise in Washington DC. You and your guests will enjoy a holiday 3-course, plated dinner freshly prepared by our chef, full bar service, and City ... More

Step aboard the iconic Cap Streeter for an unforgettable evening cruise departing from Navy Pier. Shoreline’s Special Event Series combines curated local beverage tastings, delicious light bites, music, and breathtaking skyline ... More

Explore the Chicago River in a unique way with this 120-minute Guided Ghost Tour. Learn about the city's haunted history, including the Great Chicago Fire and the Eastland Disaster. You are welcome to bring your own beverages and ... More

Take part in a unique evening Happy Hour Cruise, featuring fresh craft beers while cruising the stunning Chicago skyline. Every Thursday and Friday evening, this 2-hour experience begins on Lake Michigan, sails through the locks, ... More

Get views of Chicago’s most famous buildings, as well as insider info from an expert guide, on this time-saving, architecture-focused cruise. See the city's most important buildings all on one tour—including the Willis (Sears)... More

Enjoy a serene evening on Lake Michigan with a private sunset sailing charter, where the stunning Chicago skyline transforms as the sun sets. Departing from Montrose Harbor, this exclusive experience offers a cozy atmosphere for d... More

This tour is the perfect way to experience the shoreline of Chicago in a new and exciting way! Our tour vessel is a former military Williard Marine, which provides a unique and interesting touch to the normal tour experience. Bei... More