Chicago Boat Rentals

Take a cruise on Lake Michigan. Get a Chicago boat rental with captain!

The Sophisticated Lady: Chicago Chartered Boat Rental

The Sophisticated Lady is the perfect choice for smaller size parties looking for charter boats in Chicago. Unlike certain types of charter boats in Chicago, ‘The Sophisticated Lady’ has ample space for you and your Chicago boat cruise. This gorgeous Chicago yacht can accommodate up to 49 passengers in luxurious comfort, and give you a tour of Lake Michigan with all the trimmings. The Sophisticated Lady is the largest motor yacht of the charter boats in Chicago in the 49-passenger category. We are always happy to help you with your Chicago boat rental!

The Sophisticated Lady Chicago Boat Rental Service

Chicago Boat Rental for Parties

The perfect yacht for your special events and parties! If you are looking for a luxury yacht that is sure to impress for corporate events, then book a business cruise on the Sophisticated Lady! Plan ahead and book your Chicago boat rental with us today!

Show your employees and clients that you care about their efforts and business. If you want the most elegant business cruise in Chicago, then The Sophisticated Lady is what you need! Take a party cruise around Chicago on board one of the finest yachts to set sail on Lake Michigan!

Chicago Boat Rental for parties
  • Birthdays
  • Anniversaries
  • Bat Mitzvah's and Bar Mitzvah’s
  • Baby Showers
  • Family Reunions
  • Graduations
  • Bachelor (ette) Parties
  • Retirement Parties

Chicago Boat Rental for Weddings

An elegant wedding on the water! When you book a Chicago party cruise rental on our luxury yacht, you will have the opportunity to set cruise across second largest of the Great Lakes! You can explore the coast of Chicago and experience the city in an entirely different way! On a warm Spring or Summer day, you can soak up some sun and enjoy the nice cool breeze of Lake Michigan! In the evening you can watch the beautiful sun set across the horizon, while you enjoy a relaxing drink with you friends and associates. Be sure to book a wedding boat rental in Chicago today on The Sophisticated Lady, a luxury yacht!

Chicago boat rental for weddings

Your Chicago boat rental experience will be divine! Your cruise aboard the Sophisticated Lady begins at Burnham Harbor (near Soldier Field and McCormick Place) and heads north. You will cruise by Adler Planetarium, Buckingham Fountain, Chicago Yacht Club, Navy Pier, circle inside Navy Pier to see all festivities, further north by the beaches and back to Burnham Harbor. Make your next Chicago boat rental on board The Sophisticated Lady!

Chicago Boat Rental for other events

  • Sweet Sixteen
  • School Events
  • Fundraisers
  • Prom Cruises

Chicago Boat Rental for Business

If you are looking for a luxury yacht that is sure to impress for corporate event, then book a business cruise on the Sophisticated Lady! Show your employees and clients that you care about their efforts and business. As the most elegant business cruise rental in Chicago, the Sophisticated Lady is the ticket! Take a business cruise around Chicago on board one of the finest yachts to set sail on Lake Michigan!

Chicago boat rental for corporate events

Chicago Boat Rental for many types of corporate events

  • Entertain Clients
  • Promotion Cruises
  • Holiday Party
  • Retirement Party
  • Business Meeting
  • Team Building
  • Brainstorming Sessions
  • Networking Event

Chicago Boat Rental Entertainment

Your Chicago boat rental has certain perks! If there is an event going on during your cruise on Lake Michigan, then our captain can dock the Sophisticated Lady near the event, so you can enjoy free fireworks, concerts and even the Chicago air show! That's some free VIP level entertainment!

watching the fireworks on a Chicago boat rental

Chicago Fireworks

Fireworks shows in Chicago occur on Wednesdays and Saturdays throughout the summer, from Memorial Day through Labor Day. What a way to end an evening on your Chicago boat rental! You can learn more about the Chicago Fireworks schedule at

The Chicago Air Show

The Chicago Air & Water Show is an annual air show held on the shore of Lake Michigan in Chicago, Illinois. Book a Chicago boat rental with The Sophisticated Lady and enjoy the show! The air show has been held each year since 1959 and is Chicago's second most popular festival. For more information regarding the current schedule, check The City of Chicago's Website.

Concerts by boat

There is always a concert going on at the Huntington Bank Pavilion! Enjoy a concert with your Chicago boat rental! If you book an event during a concert, then our Captain can dock The Sophisticated Lady close by the event! Your party can enjoy VIP concert on the waters of Lake Michigan! For a complete list of concerts, please check out the Huntington Bank Pavilion.

What Are Customers Saying About Chicago Boat Rentals?

Chicago Boat Rental Reviews

Chicago Boat Rentals
Average rating:  
 16 reviews
 by Xin Huang
Overall, highly recommended Chicago boat rental!

Sophisticated lady is a gorgeous boat, I really like the myriad of spaces where you can sit down and talk or dance or just take in the view.
The food on the boat is excellent and the crew is very attentive.

Overall, highly recommended.

 by Ken Noreikis
Very responsive and attentive to details!

I reached out to Kim on short notice to book a cruise for a special event. Kim spent Sunday working out the details of cruise. She was very responsive and attentive to the details. The evening of the cruise was fantastic, a good time was had by all. Captain Bill and his entire crew were responsive and made sure everyone had fun. The evening cruise and view of the city at night was spectacular. I would recommend booking the Sophisticated Lady for your cruise.

 by Stephen H via Google
Excellent experience on the yacht.

Excellent experience on the yacht.

 by Suzanna H via Google
An enjoyable family event aboard The Sophisticated Lady!

Very nice trip for a family event. Saw the fireworks at Navy Pier. Staff was very nice and boat was beautiful. Very enjoyable.

 by Genna
The Sophisticated Lady is beautiful!

10/19/17 Cruise

Thank you for all your work with our cruise this morning. The guests were thrilled and had so much fun. Not to mention it couldn't have been a more perfect day!!

Captain Bill was fantastic and so was his crew. He was such a pleasure to work with. He was very prompt and on top of everything. I felt very confident knowing he was in charge. Please tell him thank you.

The Sophisticated Lady is beautiful.

Thanks again and I look forward to working with you soon.

 by Lucy Pesa
An amazingly planned yacht trip!

9/1/17 Cruise

It was amazing, Kim, we had a fantastic time! The captains and crew were so great and the weather was perfect. We can't wait to do it again next year!

Thanks so much again for all your help! We took a ton of beautiful pictures and are happy to share them with you for your Facebook page if you'd like, let me know anytime!

 by Connie
The Sophisticated Lady is wonderful!

8/9/17 Cruise

The yacht was wonderful and we had a great time!

 by Jennifer Scarangella, Executive Assistant: Chicago Cubs
Corporate yacht cruise for the Chicago Cubs!

7/22/17 Cruise

We had a great time on the cruise. Thanks so much for your help in making it a great event! Your staff (and the yacht!) were truly fantastic.

 by Kim Baker, Administrative Assistant: Capital One
A wonderful time at sea! Company loved the trip

5/17/17 Cruise

I have to say that the Captain was my favorite part of the day! I got to sit beside him and I could listen for hours to all the history and stories he shared. The crew was very attentive and responded to any requests quickly. I’m not great at taking pics, but here are a few from the day!

 by A Google User
The best Chicago boat rentals!

Enjoyed a concert on the water with my Chicago boat rental. I have been to see Rush 15 times in my life and watching them on Northerly Island from this boat was a special treat. The staff was friendly and helpful. We then finished the night viewing the fireworks show from navy pier. It was the perfect end to a perfect trip on my Chicago party cruise.

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