Ahoy, Captain! Explore Chicago’s Waterways on a Family Boat Cruise

Tall Ship Windy

Navigate Chicago's waterways and feel the spirit of centuries past in a 75-minute authentic tall ship sail. Tall Ship Windy is a great place to be for viewing Navy Pier's weekly fireworks and the annual Air & Water Show in August.

Online: tallshipwindy.com

Chicago Fireboat Tour

Two Navy veterans and licensed Captains invite you to cruise on a piece of Chicago history. Built in 1936, the Fred A. Busse was the largest diesel-powered Fireboat in the world and served the Chicago Fire Department from 1937–1981. It was built specifically to fit underneath Chicago’s bridges, minimizing response times for emergencies and helping ease congestion in a booming city. Upon her retirement, she was converted into a passenger vessel and operated tours in Sturgeon Bay, WI for almost 30 years. Her new owners, Ray Novak and Erich Totsch, renovated the retired fireboat and she is now cruising the Chicago waterways once again!

Online: fireboattours.com

Chicago Architecture Center's First Lady

Chicago Architecture Center has been running their very popular 90-minute cruise aboard The First Lady for over 25 years. Their expertly trained docent volunteers share fascinating stories behind more than 50 buildings and educate on how Chicago grew from a small settlement into one of the world's largest cities in less than 100 years. 

Online: architecture.org

Seadog Cruises

It’s fast and furious aboard the 75-minute Seadog, which jets off from Navy Pier, speeds along the lakefront, then zips down the Chicago River. The fast-paced excitement makes it the most kid-friendly architectural cruise of all. Little ones love this bright red and yellow speedboat, which usually has dogs on board (bring your pet along!) and funny guides. Parents appreciate learning more about Chicago’s most famous riverfront buildings, including the Tribune Building, Willis Tower, Lyric Opera and Merchandise Mart.

Online: seadogcruises.com

Kayak Chicago

If you’re looking for a truly unique perspective of Chicago, hop into a single or double kayak and paddle your way along the river with the help of an expert guide. Kayak Chicago offers rentals, as well as guided tours and individual and group instruction. Kids of all ages are welcome to ride along with an adult, but if they want to paddle a kayak of their own they need to be at least 12 years old. On the guided architectural tour, you’ll circle the loop, glide past the spot where the first settlers to Chicago set up their home base and discover the location of a former Capone-era hideout.

Online: kayakchicago.com

Urban Kayak

Two brothers and a lifelong friend who are native Chicagoans and self-proclaimed avid adventurers set out to showcase their hometown in a unique way. Their kayak tours will leave you with a newfound love for Chicago and if it awakens an adventurous beast in you, you can purchase a membership to visit again and again. 

Online: urbankayaks.com

Shoreline Water Taxi

Shoreline Water Taxis are a cheap, convenient and fun mode of city transport. Travel via the Chicago River to Chinatown, Navy Pier the Museum Campus, Willis Tower, Michigan Avenue and Union Station while feeling the wind whipping through your hair. Shoreline Water Taxi service begins in April and runs through September, with additional service throughout the fall and for special events.

As of Aug. 3, the water taxis were still not operating. But, check their website for any changes. 

Online: shorelinesightseeing.com

Shoreline Sightseeing Tours

Shoreline has deep roots in Chicago, now three generations in! With 11 major touring vessels (and their 8 water taxis) they run architectural river tours that give highlights and history of Chicago's buildings and Lake Michigan tours that show off our beautiful skyline. You can grab a Shoreline cruise from Michigan Avenue Bridge, Navy Pier's Polk Bros Park and Lake tours from Navy Pier. 

Online: shorelinesightseeing.com

Wendella Boats

Wendella is the OG in Chicago architectural boat tours, in operation since 1935. Learn about 130 years of architectural innovation and the world-renowned architecture from one of their expert guides. Make it extra special by booking a sunset cruise and toast the end of the day as the sun sets on Chicago. 

Online: wendellaboats.com

Mercury Cruises

Running continuously for the last 85 years, Mercury is experts at showing the highlights of the city in their 90-minute sightseeing adventure. They host 3D Fireworks Cruises that add excitement with the addition of 3D glasses and their Canine Cruise allows your pup to feel the wind in their fur. 

Online: mercurycruises.com