Rent a boat in Chicago

Add your dates
All boat types
With or without captain
Add people
23 boats available

Fantastic charter aboard this Carver 42ft in Chicago, IL! (2015)

From €2,985 per day


Multi Level Luxury Yacht Rental in Chicago, Illinois for up to 12 Guests (2004)

From €1,800 per day

 6 · Private · Super owner

Sail Chicago's Largest Cruising Catamaran (2004)

From €4,286 per day


Motorboat Azimu 62 1166hp (2017)

From €1,325 per day


Oustanding Fishing Charter on Trojan 36ft in Chicago, IL! (2000)

From €695 per day


Affordable boat rental without skipping out on luxury (2008)

From €1,300 per day


Believe. Tours Chicago (1998)

From €500 per day


Gorgeous Carver 38ft now available for charter in Chicago, IL! (2015)

From €2,985 per day


Breathtaking Diving charter around Chicago, IL (2000)

From €2,266 per day


Party Boat in Chicago (2015)

From €2,200 per day


Lady Janelle - 50ft Sea Ray (2015)

From €2,985 per day


Motorboat Pontoon Custom (2015)

From €2,200 per day


Amazing Charter on Sea Ray 50ft in Chicago, IL! (2015)

From €2,985 per day


Private Luxury Yacht in Chicago - 45 Passengers (1978)

From €8,905 per day


Hunter 31 for private charter in New Buffalo, MI! (2015)

From €1,086 per day


Sailboat Hunter 33.5 10.06m (1989)

From €53 per day


Motorboat Atlantis 220 Tri-log 25hp (2014)

From €1,000 per day


Motorboat Atlantis 220 25hp (2014)

From €350 per day

Boat Rental Chicago- Let’s sail Lake Michigan!

Blessed by the ubiquitous embrace of water, Chicago lends itself to a unique boating experience. With a boat rental in Chicago, admire the city in a whole new perspective by admiring its impressive skyline from the deck of your boat, while cruising along the Chicago River.

And of course if you rent a boat in Chicago you can explore the magnificent Lake Michigan, one of the largest bodies of water in the United States with a variety of boating destinations to discover dotted along the coastline.

What is the price to rent a boat in Chicago?

In Chicago, boat charter prices range depending on a variety of factors. Such as the age and size of the vessel, the duration and the season of the rental, as well as if additional requests are made such as skipper, crew, and water sport equipment. So when choosing the right boat for your trip, be sure to consider these to stay within your budget.

  • Pontoon boat rentals in Chicago start at €280/2 hours and may accommodate 8 guests.
  • Rent the largest chartering catamaran in Chicago for €1,000/day suitable for 13 people.
  • Motorboat rentals cost about €3,100/day with 12 people on board- the perfect party boat!
  • On Lake Michigan, the average cost of a fishing charter starts at €900/day for 6 guests.
  • If you are looking for an adventure, diving charters start at €130/diver.

Where to sail in Chicago

With a boat rental in Chicago, you can discover the city’s history and great views from the water as well as explore the shorelines of Lake Michigan. Find a boat in one of the 10 beautiful marinas that make up the Chicago Harbor such as Belmun, Burnham, and 31st Street marinas.

  • Navigate the Chicago River and admire some of the famous riverfront buildings- Marina City, Tribune Tower, Lyric Opera, McCormick Bridgehouse, Merchandise Mart, Grant Park, and Magnificent Mile
  • Set sail on St. Patrick’s Day and navigate on a green Chicago River!
  • Sail to Indiana Dunes National Lake Shore, and admire the sand dunes from the water.
  • Saugatuck is a unique town with award-winning beach and scenic waterways.
  • Cruise to Mackinac Island located in the north of the lake and visit the charming little town full of eateries, galleries, and plenty of history.
  • Want to set sail in calm waters? Grand Traverse Bay is a must!
  • New Buffalo is a beach town with plenty of entertainment and beaches to relax on.
  • Rent a boat for a few hours and enjoy fireworks as well as Chicago’s skyline from the lake.
  • Set sail for Lake Michigan’s western shore towards Door County, Wisconsin, a popular boating destination in the summer with lots of activities and events.
  • For those feeling adventurous and wanting to set sail on a longer trip, consider sailing America’s Great Loop. The Southern part of Lake Michigan opens into the Mississippi River, allowing boaters to start their long-term journey.

What is there to see and do in Chicago, Illinois?

After you have explored Chicago, Illinois and Lake Michigan by water, there are still many things to see and do by land!

  • Take some time to walk around the Art Institute of Chicago as well as the Museum of Science and Industry.
  • Get an up close view of the iconic Cloud Gate or the ‘Bean’ and Millennium Park.
  • Head for the Clouds and admire a 360° view of the river & city from the Willis Tower Skydeck.
  • Relax at some of the nicest beaches in town like Oak Street, Osterman, and North Avenue Beaches.
  • Spend an afternoon riding a bike or walking along the Chicago Riverwalk, home to many restaurants, bars, and shops.
  • Have a day of fun at the Navy Pier, one of Chicago’s top attractions with food, entertainment, and rides.

When should I charter a boat in Chicago?

With more than 26 miles of lakefront and 29 stunning beaches, the best time to go boating on Lake Michigan and around Chicago is during the warm summer months. From May to September, visitors can soak up the sun, as well as relax on the beaches and practice water sports. For the warmest waters around +70°F, rent a boat in the months of July and August.

Can I rent a boat with a skipper?

Avoid typical crowded boat tours and instead rent our own private boat with a skipper who knows the city of Chicago and its surroundings like the back of their palms. By using Click&Boat, you can find a variety of boat charters with captain and/or crew.

Sit back and enjoy your time on board, no need to worry about navigating, docking, and anchoring. Chartering with a captain is the perfect option for those who do not have boating experience and qualifications as well as for those who would rather relax during their trip.

The request of a skipper (and crew!) may come at an additional price depending on the size of the vessel, number of crew members and if there are any specific requests.

Where to rent a boat in Chicago?

With Click&Boat, the leading boat rental service, you can find a large range of boats, from motorboats to large catamarans to set sail in and around Chicago.

A yacht charter in Chicago, whether it is with a private or professional owner has never been so quick and simple. All you need is a few minutes to search and book the boat of your dreams!

Rely on our platform’s integrated messaging tool for our owners and renters to connect, up-to-date availabilities and prices, and a team of expert advisors who stand ready on deck to help you plan your next sailing holiday.

Opting for Click&Boat for your next Chicago boat rental will allow you to save money too- rental costs can be up to 40% lower than those offered by traditional agencies. So what do you say, are you ready to set sail with us?

Our client reviews
4.7 / 5
133359 reviews ·
See all reviews