Chicago Destination Guide

Rent a boat and head out on Lake Michigan and other Chicago waterways!

Get out and play! Top destinations for Chicago boat rentals.


Chicago boat rentals are the best way to get outside, set sail, and let the windy city waterfront be your playground. We’ve compiled the ultimate Chicago boating guide to help you amp up your experience on Lake Michigan. And if you’re looking to rent a boat in Chicago, we’ve got just what you’re looking for!

Chicago has the nation’s largest municipal harbor system, a world famous architecture skyline, and enough attractions to satisfy any boater. From Navy Pier and the Chicago River to day trips to beautiful Lake Geneva — we have you covered. No matter what you are seeking, you can find it here – whether you are looking to pull up to the best oysters in the city dockside from your yacht, to bring your friends tubing on the open water, to find a booze cruise on a pontoon boat along the Chicago River, to cruise to a beach to view dunes or to simply find the perfect place to drop a line for freshwater fish, Chicagoland has it all!

Soaking in the City Skyline on Chicago boat rentals

Chicago natives know all about the famed Chicago Riverwalk, but if you are in just for the weekend, no Chicago experience can be complete without experiencing the Chicago Riverwalk. Get a unique view of the wide variety of architecture of the city by boating up and down the South bank of the Chicago River.

Or consider letting your Chicago boat rentals take you out for a half-day ride in a Sunray Seadancer and see the iconic architecture on your own terms with your own crew in tow. Cruise along the art deco skyscrapers and experience the city skyline up close from the water.

“Chicago’s Waterfront Playground” — Navy Pier

Navy Pier on the shore of Lake Michigan is the most visited attraction in Chicago and all of the Midwest. Come summer time, this city waterfront lights up with activity including a wave wall, a centennial Ferris wheel, and weekly fireworks, taking place on Wednesdays and Saturdays from Memorial to Labor Day. From Navy Pier you can also enjoy world-famous sailing competitions and concerts taking place all summer along this 3,300 foot pier.

Be a part of the action, but away from the crowds, by powering out to the Chicago Harbour Lighthouse, east of Navy Pier at the start of the Chicago River and taking in the scene from your own private boat with Chicago boat rentals. Hear your favorite bands playing live at the local restaurants as you relax on the open water, watching the Air and Water show away from the crowds with your own private view. Set sail for VIP experiences like no other.

Interested in taking in history and watching the oldest annual freshwater distance race in the world? Catch the 333-mile Chicago Yacht Club Race as it begins off Navy Pier by the Chicago Harbour Lighthouse as you watch from the comfort of your own boat.

Waterfront Restaurants — Throw A Line & Dock Your Boat

Chicago boasts award-winning restaurants sure to impress any foodie, the best of which are accessible by boat. In the mood for farm to table, fresh cocktails, oysters and champagne? Whatever your fix, the Chicago restaurant scene can deliver. You can’t beat the atmosphere and the views, just pull up to a dock, tie in, and go ashore.

From the renowned Bridge House Tavern to pulling up to a tiki bar for fresh oysters or local catch while overlooking Lake Michigan, tie into a slip throughout the city proper or outlying suburbs to satisfy your appetite from your day on the open water.

Set Sail or Let the Motor Open — Day Trips on Lake Michigan

Lake Geneva
Ready to jet out to sea or to let out the sails, catch the wind, and soak up the sun?

Forty-four miles west of Chicago, lies Lake Geneva, adjacent to Fox River, and a perfect boating destination. Spend the day tubing with friends or dropping a line to catch freshwater trout and salmon, native to Chicago waters, and then pull up to one of the many available slips to enjoy a waterfront restaurant.

Vermilion River at Oglesby
Ninety miles southwest of Chicago lies Vermilion River at Oglesby, the only whitewater stream in northern Illinois. This might be the destination for you if you are seeking a thrilling rafting experience to pump up your senses.

Port of St. Joseph & the Indiana Dunes National Lakeshore
To the east of Chicago lies the port of St. Joseph, another beautiful boating destination ideal for a day trip on the water. If it’s a day made for sailing, grab your first mate and a cooler of beer and head east until you reach the charming lakeside town of St. Joseph. Be sure to head south enroute to St. Joseph in order to experience the Indiana Dunes at the National Lakeshore.

Summer is here and the open waters are calling your name. Enjoy these Chicago boating destinations and please let us know your favorites in the comments.


Set sail and let the adventures begin!

Beneteau 393

This beautiful 40 foot sloop-rig sail boat is praised for its beauty, comfort, and performance. Amazing cabin spaces include comfor bedding and bathrooms, plus climate control options for each.

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Carver 36 Supersport

This Carver Supersport is in brand new condition and ready to host your next water excursion. You will enjoy a custom stereo speaker system, salon with comfor room for dining; full restroom with shower, 2 staterooms and a convertible couch.

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Sea Ray 300 SLX

Anchor by the Playpen or Dunes, cruise down the Chicago River, or just enjoy a lakefront trip, all seats are outside so there is plenty of space for your group (max 10) to enjoy a day on the water.

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Set Sail in Chicago

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