Sailing in North Side

Select Local Merchants

• 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

Gliding across Lake Michigan, the sailing party watches the sun sink beneath the Chicago skyline. As the last rays fade from view, the city's skyscrapers throw their light onto the lake's surface. The captain steers the ship past Grant Park and Millennium Park, and then veers out toward Navy Pier, where the ship's passengers find a prime viewing spot for the Saturday-night fireworks show.

In addition to charters like these, the captains of Go Sailing Chicago—all holding US Coast Guard Master Captain licenses and certifications from the American Sailing Association and US Sailing—furnish beginner through advanced sailors with sailing gloves and life jackets before leading hands-on instruction in proper seamanship. Launching from DuSable and Monroe Harbor, and sometimes other points along the lakeshore, Go Sailing Chicago's four-boat fleet meets or exceeds the safety standards set down by the USCG and the most persnickety of ship-in-a-bottle builders.

3600 North Recreation Drive
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 down the Chicago River at night to ooh and ahh over summer fireworks or during the day 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

Proclaiming itself Chicago's only licensed jet-ski rental company, the outdoor enthusiasts at Windy City Watersports let visitors ride off into Lake Michigan from the tip of Montrose Beach. Every rental—which may be secured online or by flashing the lights atop the tallest nearby building in Morse code—includes life jackets, fuel, and storage for riders' possession.

1601 N Lake Shore Dr.
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

In 1935, Albert Borgstrom, a Swedish immigrant and carpenter by trade, set about constructing a 65-foot wooden yacht. He named the ship The Wendella and charged visitors $0.25 to ride through the city and listen to a guide expound on the sights. This simple vessel ended up being a steppingstone, and 75 years later, guests still ride along, now craning their heads back at the jagged opalescent silhouette of Trump Tower and the beehive curves of Marina City. Beneath the evolving skyline, the fleet has expanded to six vessels, which are now run by Albert's grandson, Michael Borgstrom. Wendella staffs a dedicated, in-house education department to keep the city's history alive and make sure that people continue to believe in water so it doesn’t disappear. On special excursions, the crew stocks the boats with wine for tastings beneath the stars or points the vessel through the verdigris waters of the lake to watch evening fireworks shows.

400 N Michigan Ave
Chicago,
IL
US