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About Us

Kayak Chicago is Chicago's premier full service outfitter, offering the highest quality instruction and trips, with our fully certified instuctors and guides. We pride ourselves in giving you the best customer service, instruction and on-water experience. We love kayaking and want to share the fun and knowledge with you. Let us teach you the skills and techniques so you can get out and explore life from the water.

How it began

In 1999, after studying outdoor education at Northland College, owner Dave Olson found himself back in Chicago after a bike trip across Europe that ending in 6 months of Mono.  With the vision of guiding trips around the world, Chicago brought a unique opportunity to share the outdoors and his love of paddling in an urban environment.  Dave began teaching classes on Lake Michigan, and helping organize the Wild Onion Urban Adventure race.  Training adventure racers was exciting, but decided to open up the world of paddling to not only athletes, but to people of all abilities.  Dave began working with Chicago area rehabilitation hospitals to help people with physical disabilities get a change to try kayaking.  The adaptive paddling program was born!  With racing and adaptive paddling, there was ony one thing missing; everyone else.  Dave began opening the doors of paddling to people in the city that had never thought about kayaking in Chicago.  He began taking people on guided tours through the city on the Chicago river.  The river had not seen so many kayaks and canoes since the Potowatamie, and what an amazing experience it was.  Today, our guided tours, classes and rentals give everyone in Chicago the ability to enjoy Chicago's waterways the way it was intended.

Meet our Staff

We have an eclectic staff of paddlers from around the world, with certifications from the ACA (American Canoe Association), BCU (British Canoe Union) and ICU (Irish Canoe Union).  Our instructors and guides hold certifications in a range of diciplines, from SUP (stand-up paddle boarding)  Kayaking, and canoeing.

Our incredible Staff will make sure your experience is exciting, safe and memorable.

See you on the water!

Senior Staff / Guides

  • Dave Olson
  • Kasia Olson
  • Jay Spriggs
  • Kelly Lagerholm
  • Luis Caro
  • David Plascencia
  • Brian Westrick
  • Tom McClanahan
  • Todd Schaffer


  • Brian Kretchmer
  • Sam Huff
  • Max Pohlman
  • Artem Abacumov
  • Alan Sidlo
  • Mike Roberts
  • Kris Polinski
  • Laura Sowers
  • Matt Churilla
  • Chris Laham
  • Cori Donohoe
  • Mary Lou Cerami
  • Hatie Parmeter
  • Elie Rivkin
  • Brian Gallagher
  • Charlie Fritschner
  • Corey Mcdermott
  • Dustin Pellegrinin
  • Karla Bernasconi

Outfitting paddlers since 1999