Kayak Tours from Urban Kayaks (Up to 50% Off). Four Options Available.
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Kayaking tourists gaze upon Chicago’s scenery from the Chicago River and Lake Michigan

Choose from Four Options
- $65 for a weekday tandem-kayak Historic Chicago tour ($130 value)
- $33 for a weekday single-kayak Historic Chicago tour ($65 value)
- $45 for a guided tandem-kayak Chinatown or downtown intro paddle ($90 value)
- $23 for a guided single-kayak Chinatown or downtown intro paddle ($45 value)
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About Urban Kayaks
Brothers Aaron and Asher Gershenzon and friend James Morro grew up in the city, but always possessed a passion for the outdoors. They practiced wilderness kayaking for most of their lives before earning their American Canoe Association certifications on Lake Superior. Each of them brings dual passions for their home city and outdoor sports to the company’s guided group and private kayak trips. Guided paddles change on every outing as guides blend downtown architectural commentary and little-known gangster stories with tie-ins to current events. Though each guide tells different stories, often interspersed with humor, all of them focus on environmentally friendliness. Paddling trips utilize a fleet of lime-green Confluence Watersports kayaks, and staffers often wear lime-green shirts—all of which render them easily identifiable from the riverwalk, but well camouflaged in supermarket produce sections.
Up to four guides lead groups of 15 kayaks or less and prepares them with a briefing on paddling techniques, rules of the river, and assurances of the stability of their wide recreation kayaks. The guides' watchful eyes and constant advice have instilled confidence in even the most unsure participants, When not guiding trips, staffers extend their easygoing atmosphere to their office—nestled across the river from the Centennial Fountain's Water Arc—where the storefront lies amidst the bustling city that surrounds it. Inside the shop, the owners' much-beloved pooches frolic around a hanging hammock.