The glass-walled boat glides past Chicago’s skyline on elegant evening cruises, complete with a three-course meal and live music

USCG captains and certified instructors welcome sailors aboard 30-ft. or larger boat

Fueled-up jet skis zip across the waters off North Avenue Beach

Entrees such as tilapia, roast beef, or chicken fill bellies while lit-up city skylines entrance eyes & DJs spin tunes

Historic 410 ft. cruise ship transports guests across Lake Michigan to Manitowoc, Wisconsin in four hours; meals and private room included

Experienced captains instill proper seamanship & teach beginners fundamental sailing skills in lessons on Lake Michigan

A 148-foot-long, traditional four-masted schooner sails throughout Lake Michigan for about 60–90 minutes

On a 36-ft. boat helmed by a US Coast Guard–certified captain, passengers groove to tunes from their iPod and feast on BYO food and drinks

Guides spin true tales of Windy City history and architecture, or the gritty underbelly takes center stage in the gangsters and ghosts tour

Up to three couples gather on deck of graceful sloop-rig sailboat for personalized day tours and shoreline fireworks shows