Learn why Nelson Algren called Chicago “the broker’s portage”; why a landmark Chicago building’s floors were built crooked; what’s the real deal with the Sears (now Willis) Tower and all about the city’s first vicious (and diminutive) crime boss.

This relaxing 2.5 hour kayak tour takes place entirely within the safety and beauty of Chicago’s downtown river with its beautifully landscaped river-edge promenade and kaleidoscopic view of some of the greatest American architecture of the 20th and 21st centuries.

Kayakers enjoy passing under a multitude of articulated ironwork bridges (the largest moveable bridge system in the world!); the fantastic shoreline people-watching; and the wide variety of wildlife that has been drawn to the majestic downtown segment of the Chicago River as the cleanliness of the River has improved over the past few decades.

Wateriders Classic Chicago River Kayak Tour is offered at 10am and 2:30pm generally on weekend days.

The tour can also be offered as a 7pm evening paddle Friday and Sunday nights (as available) that transports our guests from the golden glow of sunset into the romance, glitter and mystery of Chicago at night.

With the coming of the railroad and Ilinois and Michigan canal to Chicago in 1848, the city began its unprecedented boom. Along with the growth of business came the explosion of the city's shadier side - Chicago was where the term "underworld" was coined!

On select, Thursday through Sunday evenings at 7:00 PM (and anytime for groups of 8 or more), we offer our unique take on the Nelson Algren’s “hustlertown".

Kayak Chicago's river and learn about the legacy of the gangsters: from the river’s purportedly haunted spots to how Chicago’s own newspapers along with “Boardwalk Empire” characters like Johnny Torrio, Jim Colosimo and Al Capone created Chicago’s infamous violence and mayhem.

On the Shady Chicago tour you will:

• Kayak over the river's purportedly haunted site.

• Find out the amazing connection between Al Capone and O'Hare airport.

• Learn about Chicago's diminutive first crime lord, and the one who said, "There's a sucker born every minute."

The Shady Chicago kayak tour is recommended for adults, and is a great tour to take at night

(offered as an evening paddle 7pm Thursday, Friday and Sunday nights and for any scheduled tour by request)

Wateriders is pleased to announce an evening paddle on Thursday, Friday, and Sunday nights at 7PM (pending availability and requests).  Both the Classic Chicago Tour and The Ghosts and Gangsters Tour will be offered. Sign up today and see for yourself how beautiful downtown Chicago is at night.  Perfect for group events!

Enjoy our twilight kayak tour to Navy Pier and watch the spectacular fireworks display! This trip through downtown Chicago provides an elegant and beautiful way to view Chicago at sunset and after dark -- with the added fun of a great Lake Michigan fireworks show right in the middle!

Navy Pier stages world-renowned fireworks shows every Wednesday and Saturday night from late May through early September and selected Saturdays in October.

Our Chicago fireworks kayak tours depart our conveniently located 950 North Kingsbury launching point (about two miles from Navy Pier) in plenty of time to reach the pier before the show starts -- all the while taking the time to enjoy the glow of Chicago's magnificent architecture after dark.

After the show, paddle your kayak back beneath the twinkling lights of some of America's most beautiful buildings!  A night to remember and a Chicago unique experience, no doubt.

Sometimes the weather just doesn't cooperate!  Cancellation of kayak tours and workouts will be decided by Wateriders 2-3hrs prior to departure time and will be announced via our voicemail message at 312-953-9287.  Tours will not be run if strong rains or lightning are expected during any of the tour.

Wateriders requires a 48 hour cancellation policy for all reservations.  Tours do run at other times, space is limited, and so we ask that customers honor their reservations.  A no-show constitutes the use of any coupons and negates any other special offering on that day for future use.