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...

Book your architecture river cruise and gaze at the most iconic buildings along the Chicago River!

Book your architecture river cruise in Spanish and pass the most iconic buildings along the Chicago 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...

Discover Chicago's legendary architecture and the exceptional architects who created this ever-changing legacy for all to admire.

Learn of the city's history and enjoy Chicago's world-famous skyline along Lake Michigan.

Enjoy a relaxing and sophisticated lunch and brunch cruise onboard the majestic Spirit of Chicago and take in those feel-good vibes.

Enjoy a charming and exciting night out in Chicago with dinner, music and sightseeing aboard a two-and-half-hour luxury cruise on Lake Michigan.

Book your architecture river cruise from Navy Pier and admire the most iconic buildings along the Chicago River!

Watch the sun slowly set behind the city from the tranquil waters of Lake Michigan on this serene and romantic cruise.

Enjoy a charming and exciting night out in Chicago with dinner, music and sightseeing aboard the Chicago Premier Dinner Cruise.

Enjoy an adventurous river and lake cruise in Chicago on the Seadog speedboat! This cruise is an unforgettable experience.

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

Book your ticket for this Premier Plus Architectural Lunch Cruise in Chicago. Sit back and relax during a narrated tour and enjoy chef-prepared plated menus.

Enjoy a relaxed atmosphere with music and a view of the Chicago skyline and try different mouthwatering meal options on your unique cruise.

Odyssey Chicago's set to show you the city. Come aboard and have some fun with incredible city views as you enjoy great food, music, and sightseeing.