Top 10 Boat Rentals in Illinois, United States

Windy City Sailing provides World-Class sailing and power yacht charters for recreational, romantic and educational experiences to individuals and small groups of up to 10 people. Experience the thrill of sailing and Chicago sightseeing with United States Coast Guard certified captains on our custom yachts. Our charters are personal and private for your group, family or clients.

Climb aboard Chicago's largest sailing catamaran, Latitude Adjustment. 3rd Coast Charters offers private cruises and lessons for all ages and all occasions. You can enjoy your own exclusive experience with our catered Corporate Outings, Bachelor or Bachelorette parties and family gatherings utilizing our optional Yacht Concierge. From morning brunch to moonlight cruises and everything in-between, 3rd Coast Charters give you and your guests an experience that will last a lifetime. Make your special occasion memorable with one of our private cruises. Captain and crew promise a great day or evening out on the water plus concierge and catering options available to make it truly unforgettable!

Why Us? We provide two of the same party boats, each for 24 people. You can combine them together for your special bigger event. Both boats have bars with ice, grill, dancing pole, disco lights and speakers with bluetooth. PARTY BOATS CHARTERS, PRIVATE CRUISES, BACHELORETTE PARTIES, BIRTHDAY WEDDING CEREMONY by CAPTAIN, PARTIES CORPORATE PARTIES, GRADUATION PARTIES, SPECIAL EVENTS, LUXURY YACHT SAILING, LEARN SAILING.

At BBQ Pontoon you can take a private, self-guided river cruise where you’re the captain! No strangers tag along. It’s just you, kicking back with some good friends, great food, and awesome views! Get a free pizza on every cruise! All of our boats have Bluetooth-enabled sound systems.

Wilmette Boat Rentals is the only Power Boat Rental Company in Lake Michigan on the North Shore of Chicago and serves these areas: Evanston, Wilmette, Winnetka, Glencoe, Illinois. Get ready for a day of fun in the sun! Chicago summers are short and there's no better way to experience a beautiful day than cruising on the lake. Our Sea Doo Jet boats are the perfect boats for taking out the family.

ChicaGo By Boat offers Chicago's premier affordable luxury boat charters. We invite private groups of up to six passengers aboard the S/V Nightswimming for two to three hours based on our guests' needs. Whether it's your first time, only time, or just the next time--we want your sailing experience with us to be the BEST time you have this Summer.

This is a great way to see Chicago from the other side of Lake Shore Drive. Cruise the Lake front for a sunset cruise. Watch the Navy Pier Fireworks on Wednesday or Saturday nights with the city skyline as your backdrop, Take a cruise down the river and marvel at the magnificent architecture. Or spend a day in the sun anchored in the play pen next to Oak street beach and the John Hancock building.

Knot My Boat Charters is a Chicago-based company that specializes in providing our clients with luxurious, yet affordable, boat charters and event accommodations. We provide expertise gathered from 12 years of captaining and 16 years of combined hospitality experience in Chicago. Our team prides itself in providing an exceptional full-service experience to all of our clients.

Chain O'Lakes Boat Rentals at is proud to be your #1 boat rental company on the Fox Chain O'Lakes. We launched our business committed to a better way of renting pontoon boats. We make pontoon boat rental easy and affordable!

Mill Race Cyclery has been a proud part of the Fox Valley community for 36 years. We greet our customers with a warm smile, will help pick out a new bike that fits your lifestyle, and provide top notch service for your bike long after the sale. We rent bikes, electric bikes, kayaks, canoes and stand up paddleboards.