Sailing in Chicago, IL by Yacht Charter: Guide

What you should check out while in Chicago

Chicago has plenty of iconic landmarks that you can check out either by boat or by exploring the city on a casual walk. When Chicago sailing around, make sure to keep an eye out for Navy Pier and its Ferris wheel—they make for an unforgettable sight from the water! You can also dock your boat here and jump on the Ferris wheel for a magnificent view of the Chicago skyline. When you’re done, we advise getting yacht charters in Chicago, IL to cruise around the Shedd Aquarium and Adler Planetarium, and maybe take some nice snaps of their unique architecture. Speaking of architecture - you can also take an architecture boat tour on the Chicago River in a Chicago yacht rental! If you feel like strolling around and taking in a fresh dose of culture, go check out the Field Museum: it’s one of the city's most popular attractions, with more than 20 million visitors annually. The museum has exhibits on mostly everything, from dinosaurs to ancient Egypt, and it also houses the famous skeleton of Sue the Tyrannosaurus Rex, which is the largest dinosaur skeleton ever discovered.

Shedd Aquarium is another must-see, and not only from your Chicago boat rental with captain. It's home to more than 32,000 animals from around the globe--including penguins and sea lions--and features a huge aquarium tunnel that allows you to get up close with everything that’s going on.

Another pin on your travel map should point to the Art Institute of Chicago, which houses incredible pieces by famous artists like Van Gogh and Picasso. And since we’re talking art, have a stroll through Millennium Park, which features works by famous architects, including Frank Gehry who designed The Bean, a world-famous sculpture made out of stainless steel, now a symbol of Chicago.

Love water? You’ll love these activities!

Sail away. Looking for a more hands-on experience? Browse catamaran rentals in Chicago IL and get some sailing lessons, or get a sailboat rental in Chicago and take your skills to the next level. On a clear day, you'll be rewarded with stunning views of the city’s skyline and the beautiful blue waters of Lake Michigan. You can also take fun up a notch and get a party boat rental in Chicago with your best friends!

Jet Boat Touring. If you're interested in a more adrenaline-filled experience, consider taking a jet boat tour on Lake Michigan. With 360-degree turns and speeds of up to 45 miles per hour, this is a great option if you’re looking for a bit of excitement on the water.Pick up fishing! Nothing beats a day out fishing, and locals know and very much appreciate this simple activity. Whether you’re a newbie or a pro, Chicago has several lakes and rivers on which you can test out your skill, and plenty of stores to get lures, rods and everything else you might need. We suggest going big and taking a boat on Lake Michigan.

Go wakeboarding or water skiing. Chicago has many spots where you can wakeboard or water ski on Lake Michigan, including Montrose Beach in the suburb of Northfield Township, Wilmette Harbor and Belmont Harbor.

Get a kayak. Another great pastime is kayaking on the Chicago River or on Michigan Lake. This is a great way to see the city's famous architecture up close and personal, and to get a bit of exercise at the same time. Some kayaking rental companies provide a unique perspective on the city, offering tours through the city's hidden waterways.

Drop anchor on Chicago’s best beaches

If spending time at the beach is more your style, here are our top three beach picks in Chicago, the perfect fit for soaking up some sun on land or taking off from shore in your Chicago yacht rentals.

Oak Street Beach. Your first stop should be Oak Street Beach, located right in the heart of the Gold Coast, one of Chicago's most affluent neighborhoods. To no surprise, Oak Street Beach has been ranked as one of America's top 10 best beaches by TripAdvisor, and offers stunning views of luxury yacht rental in Chicago IL, plus both Lake Michigan and downtown Chicago’s skyline. It features lifeguards, outdoor grills, volleyball courts, Chicago yacht rentals and mostly everything you may desire or need, including outdoor showers so you can rinse off after enjoying some time in the sun.

North Avenue Beach. Up next is North Avenue Beach, which is a big favorite among locals mainly because it has a bit of everything. The 22,000 square feet beachfront features bike paths and plenty of amenities fit for people of all ages, starting with the very cozy beach bars and restaurants, and all the way to the open-air sport centers, bike and kayak rentals, outdoor Yoga spots and plenty more. We suggest you hire a yacht in Chicago, Illinois and pack your camera, because sunsets get really special here.

Montrose Beach. Last but not least is Montrose Beach, a popular spot with locals and tourists alike. It’s located near Lincoln Park Zoo and you can get there quickly with the city’s public transportation. It’s filled with food spots, kayak and volleyball rentals, and it also features showers and restrooms. Check Chicago boat rentals prices and rent a yacht in Chicago with the captain while here, for the complete Chicago experience. Montrose Beach is also home to one of Chicago's largest dog parks, which makes it a great place if you've brought your furry friend along.

Boating Around Chicago - Where to?

There are several nearby destinations that can be easily reached by boat rentals in Chicago, IL if you're looking for a longer cruise. Head north towards Wisconsin Dells where you'll find lots of beautiful lakeside towns that are a marvel to explore. Or look for boat rentals in Illinois and check out Door County in Wisconsin - this area has over 300 miles of coastline, perfect for private boat charters in Chicago, IL and boating activities ! Also, just across Lake Michigan lies Muskegon State Park, and its stunning sand dunes will give you quite the show when you’ll cruise them by.

Final Thoughts

Chicago is an amazing place to visit if you’re seeking an unforgettable experience on Lake Michigan and around. The city boasts a wealth of local attractions, from the towering skyscrapers that adorn the downtown skyline to its renowned beaches lining its shoreline, and whether you're planning to rent a boat or sail in on your own Chicago has plenty opportunities to offer when you explore its waters.

Here’s how to travel and vacation in one of the most exhilarating sailing destinations in America. Michigan boasts of dozens of registered docks, Marinas, and ports.