Chicago Kayak Tours

Wateriders is the original Chicago kayak tour, and has an unequaled 19-year track record of satisfied clients. Since 1997 we have led thousands of adventurous people from all over the globe on Chicago kayaking expeditions that reveal the history and architecture of Chicago, and which are unfailingly fun!

Wateriders is proud of its team, the most knowledgeable and experienced professional kayak guides in Chicago. Your safety and well-being are our first priorities, and our guides have used their expertise to safely guide countless kayakers of all experience and skill levels through Chicago’s rivers, channels and along our magnificent lakefront.

Our motto has always been to enable Good Green Fun in human powered boats when touring Chicago by kayak. When you tour with Wateriders you will see why we are widely recognized for providing the best kayak tours in Chicago: our professionals have a passion for nature and zest for bonding with our clients, the building blocks of a great kayaking experience.

All of our kayaking equipment is new or first-class and scrupulously maintained. Wateriders uses sea kayaks by Old Town, Emotion and Prijon. We offer both singles and doubles.

If you are a first time kayaker but have done some canoeing, the double Old Town Dirigo offers comfortable, stable and fun novice-level kayaking. Single kayaks can provide more experienced paddlers higher performance, and we offer quality single kayaks like the Emotion Advant Edge and the Emotion Glide — and for full bodied first timers the Old Town Vapor.

Wateriders Classic Chicago Kayak Tour

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.

Sat-Sun (check for other days)
All Season

10:00 AM and 2:30 PM
Friday 2:30 PM
Thursday 5:45 PM (EBC)
Anytime for groups of 8+
Tour Length Approx 2.5hrs

$65 per person
$60 per person (groups of +4)

Shady Chicago: Ghosts and Gangsters of Hustlertown (PG13)


With the coming of the railroad and Illinois 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!

Thursday, Friday and 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)

Be Advised PG13 Rating

Thur, Fri, Sun 7pm
Anytime for groups of 8+
Tour Length Approx 2.5hrs

$65 per person
$60 per person (groups of +4)

Fireworks Paddle! / Navy Pier Fireworks Chicago Kayak Tour


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.

Our Chicago fireworks kayak tours depart our conveniently located Kingsbury Yacht Club, 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.

Wed and Sat

5/23/15 - 9/5/15
Wednesday 7:30 PM (KYC) & 7:45 PM (EBC)
Saturday 8:45 PM (EBC)
Tour Length Approx 2.5hrs

$65 per person

Chicago KayOuts


On Monday and Tuesday evenings, join us at 6pm for the KayOut. It's an outing, it's a workout, and it's fun out on the water with our guides.

Kayaking uses the muscles of your torsos, arms, shoulders and abdomen -- all the major upper body muscle groups -- and provides the sustained exercise necessary to really burn calories and improve fitness. Paddling is a non-impact sport that you can enjoy for life. Each participant decides for herself whether to enjoy a leisurely outing through Chicago’s magnificent architecture or go for a full arm burn to offset last weekend’s excesses!

Our Chicago River KayOuts are a great way to learn to paddle, improve your kayaking skills, and enjoy the friendly fun of paddling to River City or Chinatown (as far as you can get!) with other kayakers.

Monday 6pm (KYC)
Tuesday 6pm (KYC)

All Season

$40 per person


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.