2016 Chicago Boating Guide: Charting a Course for Adventure

Lake Michigan and Chicago Skyline

The world’s best sailors and fastest sailboats made a splash in Chicago during the first America’s Cup race on freshwater in the event’s 165-year history. Forty-five-foot catamarans from the six different countries competed in this year’s America’s Cup World Series, just off of Navy Pier, at speeds of 40 to 50 miles per hour.

World-class boating in our own backyard is bound to inspire you to hit the water too. The good news is you don’t even need to own a boat to get out and cruise the lake. There are plenty of rental, charter and boat-share companies that take the hassle out of boating, leaving you to focus on the fun. Here’s our guide to summer boating in Chicago.

Boat Rentals

Just like Airbnb has revolutionized the hotel industry, the internet is making waves in the boat rental market. Booking engines like GetMyBoat, Boatbound and Boatsetter (think jetsetter on the water!) make renting a boat a pleasure cruise. Each of these sites lists a variety of boats available for rental at different local harbors.

Photo courtesy of Boatbound.

Captained Charters

If you haven’t done it before, you’ll find docking a boat can be stressful. Whether you feel a bit uncertain at the helm or just want to head out on the lake without any of the work, consider chartering a boat that comes with a captain. Similar to Uber’ ride-sharing platform, the new website Catered Cruises coordinates captained cruises ranging from $350 to $650 for six to 10 people. The service will be available at the 31st Street, 59th Street, Belmont, Burnham, Diversey, DuSable, Monroe, Montrose and Jackson Park Outer harbors.

Chicago Sailboat Charters is another option, offering captained sailboats out of Belmont Harbor and powerboats out of DuSable. Rates range from $280 for a group of six on a weekday sail, to $1,700 for a Saturday powerboat outing accommodating up to 11 people.

Boat Sharing

Another way to dive into boating without committing to buying a boat is a boat share club. Think of it as a country club for boaters that don’t own their own boats. You join the club, pay dues and boat as often as you like. What you won’t pay for is insurance, docking fees, maintenance or storage. Plus, membership in these national clubs gives you access to boats across the country. Freedom Boat Club at Chicago’s Montrose Harbor and Carefree Boat Club at Chicago 31st Street Harbor are two local choices.

Sailing Lessons

Always wanted to be a sailor but don’t know where to begin? Try out an introductory course at Columbia Yacht Club, Chicago Yacht Club, Montrose Harbor’s Corinthian Yacht Club or Sheridan Shore Sailing School in Wilmette. 

Cruise the Great Lakes

Take in the grandeur of the Great Lakes on a vacation by boat. Michigan’s appropriately named Harbor Country, dotted with harbor towns along the state’s southwest coast, is only 38 nautical miles from Chicago. Traveling that distance on the water can take you anywhere from two to eight hours, depending on your boat and weather conditions. Sure beats sitting in traffic on the Dan Ryan! Just make sure to book your dock spots for any town and harbor you want to visit weeks, if not months, in advance. There are a limited number of transient slips for visiting boaters and they’re in high demand in the summer.

Yachtico books week-long chartered boat trips with or without a captain, and has several listings in Chicago. Sailboats Inc. Chicago has a fleet of sailboats available out of Monroe Harbor.

A great first stop in Harbor Country is New Buffalo. Dock at the New Buffalo Marina and relax at the popular public beach then shop and dine in the charming downtown area. Adults can also hit up the Four Winds Casino Resort for some gambling fun.

From New Buffalo, head north to St. Joseph, docking at the Marina at Harbor Shores for a round of golf at the Golf Club at Harbor Shores. Kids will love exploring nearby Silver Beach’s historic carousel, Curious Kids’ Museum, splash pad and climbing wall.

Continue your journey north to South Haven for a stop at the Michigan Maritime Museum. Blueberry lovers should consider visiting Aug. 11–14 for the 53rd annual National Blueberry Festival.

Finally, you won’t want to miss the hip, artsy town of Saugatuck, which just scored the top spot in USA Today’s 2016 poll for “Best Small Town Weekend Escape in the USA.” Check local listings for events and activities throughout the summer, from art fairs, to farmers’ markets to food festivals.

Saugatuck, Michigan
Tower Marina, Saugatuck, Michigan (Photo courtesy of Saugatuck-Douglas Convention & Visitors Bureau.)

A worthwhile eight-hour drive from Chicago to Bayfield, Wisconsin, will bring you to Northern Wisconsin’s Apostle Islands, another Midwest boating mecca. The archipelago is home to the country’s largest number of lighthouses, which kids will love to look for and visit as you travel around the 21 islands. Dreamcatcher Sailing can help your family customize the perfect boating vacation, whether it’s a day trip or a week-long visit to Lake Superior’s sea caves, lighthouses and secluded beaches. The company can even provide multiple boats, accommodating up to 18 people, for multi-family vacations. Adventurous travelers can explore the area via kayak with Trek and Trail. Legendary Waters Resort, with its private marina on Lake Superior, makes for a great home base on land.

Apostle Islands
Apostle Islands (Photo courtesy of Dreamcatcher Sailing.)

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