Kayaking in Midlothian

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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 Al Capone 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.

One guide leads six participants and prepares them with a briefing on paddling techniques, rules of the river, and assurances of the stability of their wide-river kayaks. The guides' watchful eyes and constant advice have instilled confidence in even the most unsure participants, including basketball player Andre Iguodala, who slowly grew accustomed to his kayak by the end of his session. When not guiding trips, staffers provide their single and tandem kayaks to customers who want to explore the river on their own. They extend their easygoing atmosphere to their office—nestled across the river from the Centennial Fountain's Water Arc—where picnic tables stand by the storefront, and the owners' chocolate Labrador frolics inside around a hanging hammock.

270 Chicago Riverwalk
Chicago,
IL
US

The hustle and bustle of the city can’t touch the calm waters of Lake Michigan. There, on gently rolling waves surrounded by fresh breezes, Kayak Chicago hosts tours and lessons, and lets paddlers take to the waters on their own with rentals. Captained by Dave Olson, a kayaker for more than 20 years and outdoor educator for more than 10, the company entrusts certified instructors and guides with shaping the strokes of kayaking newbies. Their tours take aquatic explorers out on the lake at night to ooh and ahh over summer fireworks or along the Chicago River to survey the city’s renowned architecture and map out their next bank heist. The staff also plants patrons on standup paddleboards for introductory lessons or wave-top rounds of SUPYoga or SUPPilates.

1501 N Magnolia Ave
Chicago,
IL
US

Situated near Chicago Avenue at the Chicago River, Wateriders' experienced and knowledgeable guides have been leading relaxed kayak tours down Chicago?s picturesque waterways since 1997. Day and night tours explore the city's most exciting attributes, focusing on history, architecture, and eerie mob chronicles as guides provide paddling instruction and share true tales of Al Capone's mythical collection of tracksuits. Wateriders also rents its kayaks to independent paddlers who prefer to discover Chicago's sights on their own.

950 North Kingsbury Street
Chicago,
IL
US

• For $25, you get a Skyscraper Canyon Trip for one person in a single kayak (a $50 value). • For $35, you get a Skyscraper Canyon Trip for two people in a tandem kayak (a $70 value).

1726 W Leland Ave
Chicago,
IL
US

Yamaha jet skis speed across Lake Michigan like waterproofed motorcycles. They're departing from the 31st Street Harbor home base of Chicago Water Sport Rentals. The jet skis certainly offer high-velocity thrills, but the most exhilarating moments may come when riders take their hands off the throttle and survey their surroundings. The entire Chicago skyline stretches before them, with unencumbered views of Soldier Field, Buckingham Fountain, Millennium Park, Adler Planetarium, and other landmarks.

But customers don't need motor-power to access these sights. Via Chicago Paddle Rentals they supply stand up paddleboards, flyboards, and kayaks, as well as The Hobie Kayak Spin series, group paddles, paddleboard yoga, and paddleboard fitness classes. The fleet encompasses standard kayaks and specialty models such as the Hobie Mirage Tandem Island, which boasts pedal-based propulsion and magnificent sails. For elevated adventures, the team fires up FlyBoards, which use a water-propulsion system to transform people into superheros who can fly up to 40 feet in the air and dive underwater faster than Aquaman during an awkward pause in conversation.

3155 S Lake Shore Dr Dock J
Chicago,
IL
US

MunkyBoards' electronic skateboards carry riders on four-wheeled adventures throughout the city at speeds of up to 18 miles per hour. Available in two sizes with different power capabilities, boards can travel as far as 9 miles before they need to recharge—just like clown cars powered by other drivers' fear. Mushc like the boards themselves, designs draw inspiration from both futuristic imagery and contemporary transportation; decks on the shorter boards feature imagery inspired by the coveted hoverboard from Back to the Future Part II, and larger decks sport a map of the CTA's train system.

1923 W. Division Street
Chicago,
IL
US