Special Events

America’s Cup Racing in Chicago: Be a part of the very first ever America’s Cup racing on Lake Michigan. The race course will be located within the outer harbor breakwater (Monroe Harbor) with designated spectator areas for boaters eager to get up close to the action on the water. Behind all of this, the dramatic skyline of Chicago will stand as an iconic backdrop to the world-class racing. View the practice racing on June 10th or the racing on June 11 & 12th.

Engagement proposals: Look no further for a unique and  romantic engagement idea in Chicago. Plan your proposal under a canopy of stars with fireworks or during a leisurely B&B overnight. Whatever you decide we will help you plan and execute your dream!

Birthdays and Anniversary Celebrations: Our charters are personal and private for your group or family. Plan a romantic and very special occasion with a sunset cruise, fireworks or overnight. We work hard to meet and exceed your expectations, and surprises are our specialty.

Chicago Air and Water Show: The best seat in the house to watch the show along the lakefront. Escape the crowds along the shore and get close to the action while enjoying the luxury or our sailboat.
Book online

Navy Pier Fireworks: Throughout the summer the City of Chicago provides spectacular firework displays off of Navy Pier. The “Navy Pier Fireworks” are one of Chicago’s premier summertime attractions. Private Chicago firework cruises set sail every Wednesday and Saturday night. Your party will depart Belmont Harbor at approximately 7:30 pm for a sunset sail down to Navy Pier for fireworks on Lake Michigan. Saturday fireworks at Navy Pier go off at 10:15 pm. Wednesday fireworks at Navy Pier go off at 9:30 pm. You will have a premier view of the show set against the beautiful backdrop of Chicago’s Skyline. We will sail your group back to Belmont Harbor by approximately 11:00 pm. Navy Pier Firework displays begin on Memorial Day and end on Labor Day weekend. Click here to view the Navy Pier firework schedule.
Book online

Fourth of July Fireworks: July 4th Firework displays  go off  from Navy Pier and are typically launched at 9:30 pm and  concludes at 10:15 pm. Our USCG licensed captains and crew will handle everything. You can sit back and enjoy the cruise or try your hand at the helm.
Book online

Chicago Yacht Club Race to Mackinac: July 11, 2015 is the next annual Race to Mackinac. Sail over to Navy Pier to see the “Parade of Boats” and the official start of the race. Typically more than 300 boats participate in the race.

Northerly Island Concerts: Treat your party to a concert on Chicago’s Lakefront. We will sail your group down to Charter One Pavilion, events range from rock concerts to family matinees. Visit www.charteronepavilion.com for a schedule of events. We leave from Belmont Harbor and anchor east of Northerly Island.

Bed and Breakfast:  includes either a two (2) hour morning sail from 9:00 – 11:00 am or a (3) hour fireworks sail (when you book the fireworks package). Evening fireworks from Navy Pier, are on Wednesday and Saturday nights from Memorial Day through Labor Day.

2 Responses to Special Events

  1. Giancarlo says:

    Do you have a Saturday June 1st 2-3 hour charter available?

    • windycity says:


      I think the dates are mixed up…we are available on Saturday, June 6th for a 3 hour charter…is this the date that you are interested in?

      Give me a call if you would like to discuss, 773-868-0096



Leave a Reply

Your email address will not be published.