
Chicago, the Windy City, is a popular tourist destination known for its stunning architecture, delicious food, and beautiful lakefront. One of the best ways to experience the city is by renting a boat and cruising along Lake Michigan.
With so many boat rental options available, it can be overwhelming to choose the right one. That's why we've compiled a list of the best boat rentals in Chicago.
Whether you're looking for a romantic evening cruise, a family-friendly outing, or a party with friends, there's a boat rental for everyone.
From luxurious yachts to classic sailboats, the rentals offer a variety of options to suit your preferences. Some rentals even come with a licensed captain, so you can sit back and relax while someone else takes care of navigating the waters.
In addition to the boats themselves, many rentals offer additional amenities such as catering, music, and even fireworks displays. You can customize your rental experience to make it as unique and memorable as possible.
With so many options available, it's no wonder that boat rentals are one of the most popular activities in Chicago. So, if you're looking for a way to enjoy the city from a different perspective, consider renting a boat and exploring Lake Michigan.
1. Summer Of George

Summer Of George is a boat rental service that offers an educational architectural tour of Chicago via the water. The crew is knowledgeable and entertaining, providing a great experience for visitors.
The tour includes great views of the city and informative details about the buildings, construction, and planned structures.
The boat ride is smooth, and there are no issues regarding seasickness. The crew is accommodating and understanding in case of any issues.
The tour is highly recommended for those who want to explore Chicago's architecture in an engaging way.
2. Knot My Boat Charters Chicago

Knot My Boat Charters Chicago is a top-notch boat rental service that offers a fantastic experience on the water.
The company is highly professional and has excellent customer service, making the booking process a breeze.
The captains and deck hands are friendly, experienced, and accommodating, ensuring that everyone has a great time.
The boats are of great quality, and the BYO food and beverage policy makes it easy to plan for your trip. If you're looking for a fun-filled day on the water, Knot My Boat Charters Chicago is the way to go.
3. KnockOut Charters

KnockOut Charters is a first-class boat rental service that offers a phenomenal experience. Captain Chris, the owner, provides clean and roomy boats with a great crew.
Their tours are perfect for those who want to explore the lake, river, or simply hang out and swim.
The company is professional, accommodating, and friendly. The captain is always looking to make sure his guests have fun and enjoy their time.
Whether you're looking for a fun day out or a unique experience, KnockOut Charters is an excellent choice.
4. The Chicago Captain

Looking for a memorable boating experience in Chicago with knowledgeable captains at the helm?
The Chicago Captain boat rental service is highly recommended for a pleasurable time on the water.
With friendly and experienced captains like Paul and Trevor, you're guaranteed to have a great time.
Book your trip today and enjoy the adventure with The Chicago Captain!
5. Prestige Yacht Rentals

Prestige Yacht Rentals offers an exceptional boat rental service that is worth checking out. With a variety of boats to choose from, customers can select the perfect vessel for their needs.
The company is known for its top-notch customer service and reliability. Their boats are well-maintained and equipped with all necessary safety equipment.
The rental process is smooth and hassle-free, making it a great choice for anyone looking for a stress-free boating experience.
Whether you're planning a romantic getaway or a fun day out with friends and family, Prestige Yacht Rentals is a great choice for your boating needs.
6. Windy City Sailing, Inc

Windy City Sailing, Inc. is a top-notch boat rental service that offers an amazing experience on the water.
They have a beautiful boat and knowledgeable captains who make the trip even more enjoyable. The crew is friendly and accommodating, making sure that everyone has a great time.
Whether you're looking for a fun day out with friends or a memorable birthday party venue, Windy City Sailing, Inc. is the perfect choice.
Highly recommended for anyone looking for an unforgettable adventure on the water!
7. Come Sailing

Come Sailing is a top-notch boat rental service that offers an unforgettable experience.
Their captain, Mike, is accommodating and maintains their boat perfectly.
The prices are reasonable, and if you go out on a Saturday night, you'll get front row seats to the fireworks.
Come Sailing is a tour operator that you'll want to return to again and again.
8. Meridian Private Yachts

Meridian Private Yachts offers a professional and top-notch boat rental service.
Their crew is friendly, accommodating, and ensures a comfortable experience for their guests.
The boats are well-maintained and equipped with high-quality amenities, making for a luxurious and enjoyable ride.
Whether it's a bachelorette party, birthday celebration, or just a day out on the water, Meridian Private Yachts is a great choice for a memorable experience.
9. Live A Little Yachting Rental & Charter

Live A Little Yachting Rental & Charter is a great boat rental service that offers an amazing boat ride experience.
Renting a boat is easy and hassle-free, and the Captain Justin is a friendly and welcoming person who makes everyone feel comfortable.
The reviewer plans to rent from them again in the future.
If you're looking for a great boat rental experience, Live A Little Yachting Rental & Charter is definitely worth considering.
10. Chicago Sailboat Charters

Chicago Sailboat Charters is a highly recommended boat rental service that offers semi-private sails.
Their well-maintained ships are perfect for eating, drinking, and enjoying great views.
The captains are professional, flexible, and make sure everyone has a fun and safe time.
Whether you're celebrating a special occasion or just looking for a good time, Chicago Sailboat Charters is a great option. They also offer boat tours and sailing school.
11. Chicago Boat Rentals

Chicago Boat Rentals is an outstanding boat rental service that offers a memorable experience to its customers.
The staff is friendly, helpful, and always willing to go the extra mile. The boats are well-maintained, clean, and comfortable, making for a pleasant ride.
The rental process is easy and hassle-free, and the location is perfect for reaching downtown and enjoying the stunning skyline.
The company's customer service is exceptional, as they promptly resolved any issues and even upgraded their boat to a bigger one. If you're looking for an excellent boat rental service in Chicago, Chicago Boat Rentals is the one to choose.
12. Free Spirit Yacht Cruises

Free Spirit Yacht Cruises is a top-notch boat rental service that offers an unforgettable experience on the water.
With a friendly and accommodating crew, guests can relax and take in the breathtaking views of the shoreline.
The food catering is easy and delicious, making it an ideal choice for events and parties. The small group setting allows for a peaceful and intimate atmosphere.
The company's attention to detail and excellent service make it a must-try for anyone looking to enjoy a yacht cruise.