Charter Cruises

If you’ve ever experienced summer in Chicago, you know how much we love our lakefront. And if you’ve been on a Free Spirit Yacht charter cruise, you know how much fun they are. Not to mention, decadently relaxing.

Our yachts offer the perfect venue for corporate events, private parties, family celebrations or simply hanging out with friends. We offer a wide variety of cruises, custom tailored to your group.

Booking Your Charter

How far in advance should we book our special event aboard the Free Spirit or Gypsy Spirit? Once you know the date and time of day, you should contact us. If you have an alternate date/time, please let us know. Our yachts can be booked many months in advance, so better to book ahead than wait.

We cannot guarantee a date will be available for either of our charter yachts without a deposit. A deposit is required to hold a charter reservation for your event. The deposit is 50% of the charter fee. The balance, along with final guest count, is due 10 days prior to your charter date.

We Specialize In All Types of Events

Trade show client experience, product launch venue, sales meetings, company outings, client entertaining, convention groups, weddings/civil unions, showers, graduations, birthdays, reunions, afternoon lunches, fireworks cruises, sunset cruises, narrated river cruises, Air and Water show.

Learn more about our events by opening each tab!

Trade Shows & Conventions

Entertaining in Chicago?

Nothing comes close to a private yacht cruise on Lake Michigan.

Coming to Chicago for a trade show at McCormick Place? Looking for a special place to entertain clients? Few venues come close to a luxury private yacht charter on Lake Michigan.

After a long day on the trade show floor or meeting indoors in hotels, treat your guests to the best of Chicago. Enjoy our magnificent lakefront and world-famous skyline from the deck of one of our two beautifully appointed private luxury yachts.

Business entertaining doesn’t get any better than this!

Luxury Private Yacht Charters for Trade Show Entertaining or Corporate Events

We offer a full menu and complete bar packages for whatever type of event you’d like.

Whether you choose cocktails and hors d’oeuvres, an elegant dinner, an easy, casual breakfast or a luxury lunch charter, we’ll make sure that your event is a memorable one for you and your guests.

Our yachts can accommodate large groups on the spacious, multi-level Free Spirit (capacity up to 120 people) or smaller groups on the cozy and intimate Gypsy Spirit (capacity 49 guests). Both yachts are custom-designed for your guests’ relaxation and comfort.

Corporate Events

Charter a Company Party With Us!

Free Spirit Yacht Cruises offers two impeccably maintained, luxury yachts for corporate events — the Free Spirit and the Gypsy Spirit. Both yachts are available for charters in Chicago during the warm months of spring, summer and early fall.

For corporate entertaining, it’s hard to top a Chicago dinner cruise on the spacious, multi-level, Free Spirit. Custom-built to accommodate up to 120 passengers, the Free Spirit yacht is perfect for client entertaining and company parties. Guests can mix and mingle in the warm and inviting salon, relax in the shade on the upper deck, or soak up some sun on the cushioned comfort of the front bow.

Some of our corporate clients make it an annual event, booking charters for summer celebrations, employee appreciation parties and staff outings.

I cannot thank you enough for such an amazing event. It was incredible and we intend to make it an annual party!

Dayre Lashnits US Commodity Sales Manager NYSE Liffe

Looking to impress a special client or entertaining potential clients in town for a tradeshow or convention? The Gypsy Spirit is the perfect venue for groups of 49 or less. Her custom-designed interior offers the comfort, elegance, and luxury required by the most discriminating Lake Michigan charter yacht guests.

Treat your colleagues to a memorable evening, delighting in the breathtaking views of Chicago’s world famous skyline while enjoying cocktails and an elegant dinner. Or host a casual breakfast cruise with mimosas and bloody mary’s while cruising along Chicago’s scenic lakefront or the Chicago River. Talk about mixing business with pleasure!

Of course, we suggest that you schedule a viewing prior to booking either yacht in order to understand the full experience awaiting you. Learn more about corporate events aboard the Free Spirit or Gypsy Spirit.

Chicago Celebrations

Chicagoans love their lakefront. Warm weather brings flocks of fans out to the glorious parks and beaches along Lake Michigan. We also love our special Chicago Celebrations, especially when they’re celebrated in style on a private yacht charter cruise. Here are some of the super fun yacht parties available for charter:

Fireworks Cruises

Twice a week, Memorial Day through Labor Day, Navy Pier hosts spectacular fireworks displays from a barge on Lake Michigan. With two luxury yachts, we can accommodate small and large Chicago fireworks cruise events and boat parties with ease. Both yachts are elegantly appointed and oh-so-comfortable. Your guests will be impressed with your entertaining expertise!

Wednesday Fireworks
Start at 9:30pm
Cruising Time: 7 – 10pm

Saturday Fireworks
Start at 10:15pm
Cruising Time: 8 – 11pm

July 4th Fireworks Cruise
9:30pm Fireworks Display

Navy Pier Fireworks Schedule

These book up crazy fast! So you’ll want to plan ahead to reserve this cruise.

Air & Water Show

The Air & Water Show is one of the highlights of Chicago’s summer season. And there’s no better way to celebrate this exciting event than on a comfortable luxury yacht charter on the open water of Lake Michigan. Kick back, sip on your favorite drink and catch the thrills. “This year’s headliners include the U.S. Air Force Thunderbirds and new this year, the F-35 Heritage Flight.”

Cruising Time:
The Free Spirit cruises for 4 hours with a 100-person minimum private charter.
The Gypsy Spirit cruises for 4 hours with a 40-person minimum private charter.

Private Events

We make special occasions memorable!

Whatever you’re celebrating, hosting an event on one of our luxury yachts will make it even more special. We can accommodate just about any event – one that your guests will talk about for years to come. Private parties aboard our yachts offer a comfortable, elegant setting which works just as well for a casual, fun-in-the-sun outing as an upscale, sophisticated cocktail party.

Every detail of your cruise will be expertly managed. From helping you choose the perfect menu and bar package to making sure your guests are comfortable and attended to on board.

We offer a wide variety of catering options, all featuring delicious contemporary cuisine for your private parties. Let us help you select the perfect menu, whether you’re hosting a theme party (Chicago Blues Cruise) with a full dinner buffet or a simple birthday celebration with sandwiches and salads.

Luncheons & Sunday Brunch

Entertaining clients or showing off Chicago to visiting friends takes on a whole new meaning when the venue is a luxury yacht on Lake Michigan. Cruising lazily on the shimmering blue water, with the Chicago skyline as a backdrop, makes conversation easy. Big groups or intimate gatherings. Free Spirit Yacht Cruises has you covered.

Birthday Parties

Birthday on a boat! The guest of honor will remember this special day for years to come. Whether you’re inviting a big crowd or a small group of close friends, we have the perfect yacht to suit your needs.

Lake & River Cruises

The Chicago River is a unique part of our city, and one that tourists and locals alike always find fascinating. Architectural gems, old and new, line the river bank. Condos, offices, hotels, restaurants and cafes. If you haven’t seen it, you’re in for a treat.

In addition to Lake Michigan cruises, the Gypsy Spirit also cruises the Chicago River. And if you want to really learn about our city, we have a list of tour guides to narrate your charter.

A few interesting Chicago River Factoids:

  • The Chicago River System is 156 miles long and flows through downtown Chicago.
  • 52 moveable bridges span the river.
  • The river flowed directly into Lake Michigan until 1900, when the Chicago Sanitary District reversed the flow, using a series of canal locks. Today the river empties into the Chicago Sanitary and Ship Canal.
  • Garbage filled the river until the 1990s when it underwent an extensive cleaning as part of Mayor Daley’s Chicago beautification program.
  • On St. Patrick’s Day, the river is dyed bright green.

We got so many compliments from our guests – everyone enjoyed it. The boat was wonderful, very comfortable. We won’t hesitate to recommend you if anyone is looking for cruises around the lake or the river in the future. Thanks again to yourself, Captain Joe and the entire crew!

Steve Evans

Sunset Cruises

Sunset on Lake Michigan is glorious. Beautiful, peaceful, and romantic. For family celebrations, wedding receptions, dinner parties – you name the occasion, we’ll make sure you and your guests have a fabulous time.

Sunset cruises are especially well suited for celebrating your rehearsal dinner or a special wedding anniversary. For smaller events where you want to host close friends and relatives without the distraction of a restaurant venue, a private yacht is the perfect solution. Intimate, cozy and very private.

Wedding Cruises

We invite you to have your Wedding Ceremony and Wedding Reception aboard the Free Spirit or Gypsy Spirit.

If a banquet hall or hotel ballroom is not your idea of a dream wedding venue, we offer a private luxury yacht – an incredibly romantic setting for an elegant, intimate affair.

The Free Spirit (or the Gypsy Spirit) is an excellent place for you to begin your lives together. After the nuptials, your guests can begin to enjoy the reception immediately. No need to book two venues and shuttle guests between locations!

On the day of your wedding, our captain and crew will attentively handle every detail, execute your plans and warmly welcome you and your guests. All you have to do is enjoy your very special day, toast your new spouse, and celebrate with people dear to you.

I just wanted to thank you again for the wonderful evening we’ve spent on the Gypsy Spirit. Everything was really great and the service was outstanding. All of my guests really enjoyed the cruise and congratulated us on the choice of the boat! I’ll definitely recommend you to my friends! Thank you again!”

Patrycja & Hristo

Blues Cruise

Chicago and blues are synonymous. Ours is the town where the blues were born.

If you’re a blues fan, it doesn’t get much better than hosting (or being a guest on) a Free Spirit Yacht Charter Blues Cruise. Three hours of pure musical joy. Cruising Lake Michigan, the knock-em-dead Chicago skyline as a background, enjoying a custom Chicago-style menu, and listening to true Chicago blues.

Create and bring your own playlists. Or better yet, book the real thing – like Vino Louden, lead guitar and bandleader for many years for Chicago legend and “Queen of the Blues” Koko Taylor. Vino’s been around long enough to have toured with B.B. King and Bonnie Raitt. On land, you can hear him at Buddy Guy’s Legends. But you can also book him for your Free Spirit Blues Cruise. Here’s a clip of Vino playing on the Free Spirit. Talk about memorable parties!

What happens if it rains or the weather won’t cooperate?

Your charter will proceed as scheduled. Our yachts are large enough to have your group inside, the food will have been ordered, and your guests invited. We’ve hosted lots of parties and meetings when the weather was less than ideal.

Can I get a refund? Sorry, there are no refunds due to inclement weather. All bookings are non-refundable.

Do you provide beverage service or can we bring our own?

We have several bar packages, which are broken down on our Bar Menu. All numbers must be guaranteed 10 days prior when final payment is made on your cruise. At this time, the number of people attending the cruise may be increased; however, there will be no refunds if the numbers are decreased.

You cannot bring your own beverages because we have our own liquor license. Cruise guests will not be permitted to bring aboard liquor or carry it off of the yachts; all liquor must be consumed while on board the ship.

Do you provide catering or can we bring our own food aboard the Free Spirit or Gypsy Spirit for our event?

We work with the city’s finest caterers to provide an extraordinary variety of customized menus that will excite your taste buds and delight your guests. You may also customize your own menu. We highly recommended using our existing catering menus since they have been designed specifically for the yachts (and taste tested by thousands of happy guests).

Exceptions: If you really want to have your own special caterer, there is a $500 outside catering fee, and you must show proof of insurance.

Who would I know who has rented your yachts?

Who would I know who has rented your yachts? You can view a partial client list. And check out some of our testimonials.

View Our Gallery