Top 10 Water Tours in Chicago

Destination: Chicago.
The ultimate custom sightseeing experience in Chicago! Enjoy the City from great vantage points and photograph the world-famous skyline. We zip you to many sights around the local waterways including the Navy Pier, Soldier Field, Fort Dearborn, Vietnam Memorial, Wolf Point, Shedd Aquarium, and many others. Come aboard our safe and seaworthy US NAVY built Rigid Inflatable Boat (RIB), and experience a unique & personal tour of the City!
Known For: Chicago Sightseeing Cruises, Chicago Private and Luxury, Chicago Water Tours, Chicago Small Group, Chicago City Tours, Chicago Day Cruises, Chicago Excellent Quality.
Duration: Around 1 hour and a half.

Destination: Chicago.
Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline. Make the experience your own. The flexibility of a private charter allows customization of virtually any aspect of the sailing adventure from guest list to music selection to sailing route. Three departure times offered daily. This experience is not meant to be an in-depth guided tour; however, our captain is always happy to point out interesting sights with anecdotes and historical information. Just ask you captain. Looking for a sunset sail, see our other product listing "Come Sailing with us at Navy Pier - Sunset Sail on Lake Michigan". Looking to watch the Navy Pier Fireworks from a private sailing charter, see our other product listing "Come Sailing with us at Navy Pier - Saturday Fireworks Sail". All charters are NON-SMOKING experiences.
Known For: Chicago Private Sightseeing Tours, Chicago Likely to Sell Out, Chicago Day Cruises, Chicago Sailing, Chicago Water Tours, Chicago Sightseeing Cruises, Chicago Full-day Tours, Chicago Likely To Sell Out.
Duration: Around 2 hours.

Destination: Chicago.
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. Being both sturdy in the water, and fast! Reaching up to speeds of 35 Knots! We work hard to provide historical context for our great city, as well as provide an exhilarating experience through the use of high speed runs and spins!
Known For: Chicago Adventure Tours, Chicago Speed Boat Rentals, Chicago Small Group, Chicago Zombie, Chicago Excellent Quality, Chicago Historical Tours, Chicago Jet Boat Rentals, Chicago Zombie Slice, Chicago Extreme Sports, Chicago Water Tours.
Duration: Around 1 hour and a half.

Destination: Chicago.
Travel on a piece of history, learning Chicago fire history as well as Architecture! We travel through the Chicago River seeing the sights. Perfect for Fire enthusiasts, families and everyone in between! Our flagship vessel is a retired Chicago fire boat, the Fred A Busse, Engine 41, which served Chicago from 1937 to 1981. Firefighter patches from around the world and memorabilia from Engine 41's time in service, adorn the walls inside the cabin.
Known For: Chicago Water Tours, Chicago Seasonal, Chicago Sightseeing Cruises, Chicago Day Cruises, Chicago Historical Tours.
Duration: Around 1 hour and a half.

Destination: Chicago.
Enjoy a fun and scenic 90-minute Cycleboat Cruise along the beautiful Chicago River! Take in stunning skyline views as you pedal, relax, and sip your favorite drinks with friends, family, or that special someone. • 1.5-hour cruise up and down the iconic Chicago River • Comfortable boat with 10 cycle stations and bench seating at the front • Maximum capacity of 16 passengers — perfect for smaller groups or couples • BYOB! Bring your own beverages and snacks to enjoy onboard • Departs from the Water Plaza on the Chicago Riverwalk (between Wells Street and LaSalle Street bridges) Whether you want a lively group outing or a relaxing ride through the city, this Cycleboat Cruise is one of the most unique ways to see Chicago from the water — no full-boat rental required!
Known For: Chicago Water Tours, Chicago On the Water, Chicago New Product, Chicago City Tours.
Duration: Around 1 hour and a half.

Destination: Chicago.
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 food/snacks to fully enjoy your time on the water. Departing from the Chicago Riverwalk, this is a fun and engaging way to experience the spooky side of the city. This tour is typically smaller allowing for you to interact with the tour guide! Ask all the questions, we are ready! - 120-minute ghost tour on the Chicago River for up to 18 passengers - Fun bring-your-own beverage/snacks experience with a u-shaped bar and coolers - Learn about Chicago's haunted history and significant events - Departures from the Chicago Riverwalk—15-minute early arrival required to allow time for check in and depart on time.
Known For: Chicago Water Tours, Chicago New Product, Chicago Ghost Tours, Chicago Historical Tours.
Duration: Around 2 hours.

Destination: Chicago.
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, and little-known facts that shaped the Windy City into what it is today. • Chicago’s transformation from swamp land to industrial hub to the modern metropolis it is today • The dramatic story of the Great Chicago Fire of 1871 and how the city rebuilt stronger than ever • Tales of Chicago’s most infamous gangsters and Prohibition-era legends • The groundbreaking 1893 World’s Fair and the inventions it introduced to the world • The incredible reversal of the Chicago River — its purpose and lasting impact on the city’s future Step aboard and experience how history, architecture, and innovation flow together on this unforgettable journey through Chicago’s past and present.
Known For: Chicago Water Tours, Chicago New Product, Chicago City Tours.
Duration: Around 2 hours.

Destination: Chicago.
Chicago Air and Water Show 2025 Great for friends & family! PLEASE READ CAREFULLY Experience Chicago’s Air & Water Show from the Best Seat on the Lake! 10AM SAIL: Our first sail will depart at 10am sharp. Our first event will be the Air and Water Show, and will showcase a wide variety of aircraft, and demonstrations, which will be watched from the *best location, as determined by the Captain. We will return to our dock by 12:30pm. 1PM SAIL: This sail will depart at 1PM sharp. As this is our second sail for the Air and Water Show, this sail will also showcase a wide variety of aircraft, and demonstrations, INCLUDING THE MAIN EVENT. This will be watched from the *best location, as determined by the Captain. We will return to our dock around 3:30pm, but this may be delayed, if the show is delayed, to ensure your viewing of the main event, if it happens.
Known For: Chicago Likely to Sell Out, Chicago Water Tours, Chicago Sailing, Chicago New Product, Chicago Likely To Sell Out.
Duration: Around 2 hours and a half.

Destination: Chicago.
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, Italian Beef, Garrett’s Chicago Mix Popcorn, and the original Palmer House Brownie, or elevate your day with our VIP craft beer upgrade. This unforgettable Chicago in a Day Tour explores Millennium Park, the Chicago Riverwalk, Michigan Avenue, Cloud Gate, Chicago Theater, and more, guided by true local experts. Enjoy a 5-hour journey through culture and cuisine, plus a FREE 2-hour bike or kayak rental to continue the adventure along Lake Michigan. Recently honored among the “Top 10 Food Tours in America” (USA Today) and “Top 20 Food Tours in the World” (TripAdvisor), this award-winning Culinary Tour is one of the top Things to do in Chicago. Don’t miss the most delicious, scenic Full Day Food Tour in Chicago—all in one extraordinary day.
Known For: Chicago Walking Tours, Chicago Half-day Tours, Chicago Water Tours, Chicago New Product, Chicago Private and Luxury, Chicago Kayaking Tours, Chicago Food & Drink, Chicago Historical Tours.
Duration: Around 5 hours.

Destination: Chicago.
Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline. Make the experience your own. The flexibility of a private charter allows customization of virtually any aspect of the sailing adventure from guest list to music selection to sailing route. This experience is not meant to be an in-depth guided tour; however, our captain is always happy to point out interesting sights with anecdotes and historical information. Just ask you captain. Looking for daytime sailing, see our other product listing "Come Sailing with us at Navy Pier - Sail Beautiful Lake Michigan". Looking to watch the Navy Pier Fireworks from a private sailing charter, see our other product listing "Come Sailing with us at Navy Pier - Saturday Fireworks Sail". All charters are NON-SMOKING experiences.
Known For: Chicago Likely to Sell Out, Chicago Day Cruises, Chicago Sunset Cruises, Chicago Likely To Sell Out, Chicago Sailing, Chicago Sightseeing Cruises, Chicago Private Sightseeing Tours, Chicago Water Tours, Chicago Excellent Quality.
Duration: Around 2 hours.