Chicago Tours

Enjoy Chicago’s famous sights and fabulous views on this award-winning small-group sightseeing tour of the city...

Explore the best of Chicago on an intimate small-group tour with a maximum of 6 guests. Take in the city’s world-famous skyline, bold skyscrapers, and stunning Lake Michigan views while enjoying the expertise of your friendly Tripshepherd guide...

The ultimate custom sightseeing experience in Chicago! Enjoy the City from great vantage points and photograph the world-famous skyline. Come aboard our safe and seaworthy US NAVY built Rigid Inflatable Boat (RIB), and experience a unique & personal tour of the City!...

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...

Enjoy a 90-minute comprehensive boat cruise of Chicago's legendary architectural wonders from the best seat in the house, the river.

Set sail on our flagship vessel, where style meets comfort in a Tiki Chic atmosphere. As you sip a refreshing beverage, enjoy the rare experience of transiting the historic Chicago Locks—a must-see for locals and visitors alike...

Sunday Funday Mimosa Cruise – Chicago’s Floating Tiki Bar Adventure! Sundays are Fun-Days aboard our vibrant floating tiki bar, Island TIme, where the drinks are cold, the vibes are high, and the views are iconic! Cruise down the Chicago River the Island Party way—with a mimosa or Bloody Mary in hand and a front-row seat to some of the world’s most stunning architecture...

Kickstart your adventure in Chicago with the tour that started it all. Explore the grandeur of the city and soak up all the vibes it has to offer.

Hop on the majestic Odyssey for a special brunch cruise in Chicago. Start your weekend off with a splash of finesse!

Hop on the majestic Odyssey for a special lunch cruise in Chicago and start your weekend off with a splash of finesse.