Chicago River: 1.5-Hour Guided Architecture Cruise
Experience Chicago’s legendary architecture from the best seat in the house: the river. Enjoy a comprehensive tour with a live fun guide as you navigate through the he...
Cruises and boat trips.
For the operators we researched and recommend, see our food tours and cooking classes in Chicago, or the experiences overview.
On the water
Chicago River 90-Min Architecture Boat Tour
Take a guided Chicago Architecture River Tour. Cruise past landmarks, learn history, see future projects, and enjoy stops at Navy Pier and Goose Island. A unique look ...
Chicago by Night River and Lake Cruise
Glide along the Chicago River and Lakefront as you're dazzled by the sparkle of the city at night. Enjoy breathtaking views of the dramatic skyscrapers and Buckingham ...
Chicago: 45-Minute Family-Friendly Architecture River Cruise
Cruise down the Chicago River and see the city’s most spectacular landmarks on a boat cruise with live, family-friendly commentary and a full-service bar on board.
Chicago: Historic Gangsters & Twilight Tales Night Cruise
Listen to stories of Chicago's darker side, including mysterious sightings, creepy haunts, mobsters, and more, as you cruise the Chicago River amidst twilight tales of...
City Cruises Chicago: Seadog Lakefront Speedboat Ride
Admire Chicago’s skyline and listen to city insights during an exciting speedboat ride on Lake Michigan. Choose the extreme thrills option to enjoy even faster speeds ...
Chicago: Architecture Center Cruise on Chicago's First Lady
Experience a Chicago River cruise partnered with the world-famous Chicago Architecture Center, featuring live English-speaking certified docents and pre-recorded multi...
Chicago: Architecture River Cruise Skip-the-Ticket Line
Cruise along the Chicago River on a boat tour and discover hidden architectural gems among the city’s renowned landmarks, with live narration.
Chicago: First Lady River Cruise & Architecture Center Combo
Join a river cruise in Chicago featuring live certified guides and pre-recorded multilingual commentary. Book a combo that includes discounted entry to the world-famou...
Chicago: 1.5-Hour Lake and River Architecture Cruise
Skip the ticket line for Chicago’s only architecture cruise on both Lake Michigan and the Chicago River. Learn about Chicago's internationally-known architecture from ...
Chicago: Sunset Kayak Tour on the Chicago River
Paddle through downtown Chicago on a kayak tour during the golden hour. Admire the city's skyline, including the Willis Tower and Civic Opera Building, as the sun sets.
Chicago River: 1.5-Hour Guided Architecture Riverboat Tour
Climb aboard a unique 90-minute architecture riverboat tour of the famous Chicago River. Pass by over 50 significant Chicago buildings learning about their architectur...
Chicago: Guided Twilight Kayak Paddle on the River
Glide along the Chicago River as the skyline shifts into evening light. Listen to stories of iconic architecture while paddling the Main Branch.
Chicago: Historical Lake and River Fireboat Cruise
Cruise on a piece of Chicago history, the Fred A. Busse, retired Engine 41. We'll learn about Chicago's world-famous history & architecture on a guided cruise of Lake ...
Chicago: Narrated Sightseeing River and Lake Cruise
This popular 90-minute, fully narrated daytime river and lake tour delights families with incredible views of Chicago's famous architecture, stunning skyline and stori...
Chicago: Guided Sunset Kayak Tour on the River
Paddle into golden hour on the Chicago River and watch the skyline shift at dusk. Hear architecture and true-crime stories as the city lights come on.
Chicago Seadog 75-min Speedboat Architecture Cruise
Enjoy Chicago's iconic skyline with an exciting speedboat tour. View Chicago's unique architecture and famous landmarks from the water as you listen to the live narration.
Chicago: Historic Architecture Chicago River Small Boat Tour
Learn from an expert docent about the designs, world-renowned architects, and innovations behind more than 50 skyscrapers. Cruise down the Chicago River on a trip aboa...
Chicago: Private Catamaran Sailing for up to 12 people
This exclusive sailing experience includes breathtaking views of the Chicago skyline, refreshing swims, and the luxury of private yachting including Chicago’s largest ...
Door County: Deaths Door Bluff Kayak Tour
Explore Door County’s northern shores with a guided tour brings the region’s natural and maritime history to life through epic views storytelling, and stunning photo o...
Chicago: 2-Hour Kayak Rental from North Rockwell
Paddle through Chicago's urban forest along the revitalized river. Enjoy a peaceful escape surrounded by nature's beauty.
Sturgeon Bay: Cave Point Kayak Tour
Join us for a beautiful kayak trip along Door County’s pristine Lake Michigan coastline. The trip will take you along Cave Point County Park, and Whitefish Dunes State Park.
Chicago & North Shore: Stand-Up Paddleboard lessons & tour
Learn how to safely paddle board on the beautiful Lake Michigan. You will gain paddling knowledge, ability, and confidence, resulting in both a great time and lasting skills!
Chicago: Private Lake Michigan Sailing Charter
Enjoy a private sailing charter along the Chicago lakefront aboard a comfortable sailboat with skyline views, fresh air, and a friendly local captain and crew.
Chicago: Characters and Cons Guided Kayak Tour
Embark on a kayak journey through Chicago, uncovering the story of Leo Koretz, a 1920s con man. Learn about the Leopold and Loeb murder case and enjoy a unique way to ...