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Private Sunset Sail on Lake Michigan with Breathtaking Views of Chicago

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront.  Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline.  Make the experience your own.  The flexibility of a private charter allows customization of virtually any aspect of the sailing adventure from guest list to music selection to sailing route.  All charters are NON-SMOKING experiences.

per adult from




2 hours


Mobile ticket

Select Date and Travellers

No tour options available.

  • What's included :
    • Professional US Coast Guard licensed captain
    • Use of Bluetooth speakers
    • All applicable taxes
    • Entry/Admission - Come Sailing, Inc.
    What's excluded :
    • Gratuities
    • Food and Drinks
    • Parking
  • This is a typical itinerary for this product

    Stop At: Come Sailing, Inc., Monroe Harbor, Chicago, IL 60603, USA

    We’ll depart from the north side of Monroe Harbor at our dedicated pick-up/drop-off spot. Once the safety briefing is completed and all dock lines have been brought on board, our trip will begin. The itinerary, course/route we are sailing for the day, will depend mostly on wind the direction. However, being that this is a private charter, the itinerary remains very flexible and pretty much at your discretion. So, if you’d like to see a particular landmark or prefer to sail a particular route, just ask our captain and they will be happy to oblige. If, instead, you’d prefer to leave all of the decision up to the captain, no problem. Our captain will be happy to take you for an enjoyable sail on Lake Michigan during which you will sail in close proximity to some or all of the landmarks listed in the itinerary below.

    Duration: 2 hours

    Pass By: Buckingham Fountain, Grant Park, Chicago, IL 60605

    Our charter begins with a quick motor passed a part of Monroe Harbor named in honor of a visit by Queen Elizabeth II. On July 6, 1959, a small barge ferried Her Majesty from HMY Britannia anchored outside of Monroe Harbor to the aptly named Queen’s Landing for a 13-hour royal visit spectacular. As we pass this historic site Buckingham Fountain comes into view. (Pro Tip: this is a great time for a photo op.) Buckingham Fountain, one of the world’s largest fountains, was designed as a focal centerpiece for Grant Park. According to the Chicago Park District website, John Philips Souza himself conducted his band in the playing of “Pomp and Circumstance” before an audience of 50,000 people during the fountain’s dedication in August 1927. Contrary to conventional wisdom; however, Buckingham fountain has nothing to do with Buckingham Palace or the Royal Family. The fountain was actually donated by Chicago art patron and philanthropist, Kate Buckingham in memorial honor of her brother Clearance Buckingham, himself a patron of the arts and fellow philanthropist.

    Pass By: Shedd Aquarium, 1200 S. Lake Shore Drive, Chicago, IL 60605-2490

    Another building which cannot be ignored as we depart from Monroe Harbor is the Shedd Aquarium which sits prominently at the south end of Monroe Harbor. Completed in 1930, the Shedd Aquarium’s mission is “Sparking compassion, curiosity and conservation for the aquatic animal world”. The large dark windows facing the lake house the Abbott Oceanarium exhibit. Added in 1991, the Oceanarium features Pacific white-sided dolphins and beluga whales.

    Pass By: Adler Planetarium, 1300 S Lake Shore Dr, Chicago, IL 60605-2489

    Sitting on the northeast corner of Northerly Island is the iconic dome of the Adler Planetarium. Built in 1930, this picturesque public museum dedicated to the study of astronomy and astrophysics a popular location for wedding photos. As we head out into the Lake, we get to see a side of this marvelous structure that most visitors never think to investigate: the lakeside! This is where you will find the Doane Observatory which has a large telescope available to the public.

    Pass By: Soldier Field, 1410 S Museum Campus Dr, Chicago, IL 60605-2902

    Opened in 1924, Soldier Field, known today as the home of the Chicago Bears, has played host to a variety of interesting and historical events. Even though the stadium has changed drastically over the years, the original colonnades can still be seen from our vantage point on the water.

    Pass By: Navy Pier, 600 E Grand Ave, Chicago, IL 60611-3419

    One of the most recognized landmarks along Chicago’s lakefront, Navy Pier is also one of the most and visited tourist destinations in Chicago. Sailing passed the east end we’ll have a great view of the Grand Ballroom. This would be another perfect time to snap some selfies or capture a stunning architectural photo. Opened to the public in 1916, Navy Pier has played many roles during its lifetime including an important role during WWII. This piece of Chicago is definitely more than just a photo op!

    Pass By: Chicago Skyline, Chicago, IL 60601

    One of the most beautiful waterfront cities in the world, Chicago’s magnificent skyline is best viewed from the water. There are too many stories to be told about the amazing architecture, landmarks, and engineering feats accomplished in Chicago. Which ones you hear are up to you. Again, this is your private charter and you set the tone for the trip. If you prefer to just visit with friends and loved ones, no worries at all. Our captains are happy to the role of captain, guide, or both. Come Sailing and let us show you the city we love.

  • Departure Point :
    Come Sailing, Inc., Monroe Harbor, Chicago, IL 60603, USA
    Return Detail :
    Returns to original departure point
    Hotel Pickup :
    • Confirmation will be received at time of booking
    • All charter are NON-SMOKING. Use of any tobacco products, cigars, pipes, cigarettes, e-cigarettes, vapor devices, etc. are strictly prohibited. Use of any of these products may result in a non-refundable, early termination of your charter and the assessment of a cleaning fee.
    • Customers and guests are allowed to bring and consume reasonable amounts of alcoholic beverages within the bounds of Illinois State law.
    • Glass containers are prohibited. Please do not bring them.
    • Customers and guests are expected to conduct themselves in an appropriate manner. Inappropriate behavior will not be tolerated. Any behavior determined by the captain to be inappropriate (lewd, offensive, unsafe, etc.) may result in a non-refundable, early termination of your charter.
    • No guns, knives, or weapons of any kind are allowed on board our vessels at any time. Bringing any of these prohibited items aboard may result in a non-refundable, early termination of your charter.
    • Swimming is not allowed on sunset charters.
    • Food and beverages may be consumed on deck. Please clean up any spilled food or beverage and take your garbage with you. A cleaning fee may be assessed for excessive spillage.
    • Any person that experiences seasickness must remain on deck. The cabin area below deck is NOT an appropriate place for any person to deal with seasickness. A cleaning fee will be assessed for any person vomiting anywhere in the below deck cabin area of the sailboat, including the “head”/bathroom.
    • Cleaning fees will be equivalent to the standard, full price of your charter.
    • The captain reserves the right to cancel a charter at any time for reasons of weather, mechanical failure, or safety. Charters will be rescheduled at the customer’s convenience.
    • Gift Certificates may not be redeemed for cash. Gift certificates may be used to purchase products and services offered by Come Sailing, Inc. Gift certificate will expire one year from the date of purchase. The terms “gift voucher” and “gift certificate” have the same meaning and are used interchangeably throughout our website.
    • The late arrival of customers and guests may result in a shortened charter sail without refund or adjustment to price.
    • Boarding any sailboats operated by Come Sailing, Inc. is your implied consent to be filmed, photographed, and recorded. Furthermore, by boarding any of our sailboats you are granting Come Sailing, Inc., their agents, successors, assignees and affiliates, and their respective employees, officers, directors, shareholders, and representatives the right and permission to use such film, photographs and recordings and to use your name, voice, image, and likeness for the purpose of promoting Come Sailing, Inc. and its related services. You further agree that you will not receive any financial compensation or cash payment for the rights or permissions granted by you.
    • In such case that you are the parent or guardian of any minor child that has accompanied you aboard our sailboat, you further consent to the foregoing on behalf of such minor child.
    • Not wheelchair accessible
    • Near public transportation
    • COVID-19 FACE MASK POLICY - ALL passengers are REQUIRED to wear face masks covering both their nose and their mouth. If, for any reason, you are unable or unwilling to wear a face mask, please do not book a charter with our company. Masks are not provided, please bring your own. The captain and crew are REQUIRED to wear face masks covering both their nose and their mouth. The captain will explain the rules under which passengers will be allowed to temporarily remove their masks in order to enjoy the fresh lake breeze. Only under those rules and only with the captain's approval may passengers temporarily remove their masks. Passengers will don their again masks immediately upon request of the captain.
    • COVID-19 SOCIAL DISTANCING POLICY - We have cancelled all of our semi-private shared sailing experiences for the 2020 season because of the lack of social distancing space aboard our sailboats. Social distancing within your own group during your private sailing charter is at your discretion and is your responsibility. In order to safely sail and maneuver the boat the captain and crew will need to around the boat and may be in close proximity to you for short moments of time. The captain may request passengers to move to certain parts of the boat at different times to minimize the amount of time spent in close proximity.
    • COVID-19 SICK PEOPLE SHOULD STAY AT HOME POLICY - People who are sick should STAY AT HOME. We will see you when you feel better. Anyone with symptoms of COVID-19, the flu, or any other potentially contagious disease are not permitted on our sailboats. PLEASE STAY AT HOME. All passengers agree to self-diagnose and not board any of our sailboats if they have any symptoms of COVID-19, the flu, or any other potentially contagious disease. Anyone who has been exposed to persons with symptoms of COVID-19, the flu, or any other potentially contagious disease are not permitted on our sailboats. PLEASE STAY AT HOME.
    • COVID-19 RESTRICTED ACCESS TO CABIN POLICY - Due the COVID-19 pandemic, it is necessary for us to restrict passenger access to the cabin and spaces below deck. Therefore, please keep the following in mind: Passengers will not be allowed below deck (in the cabin). Passengers will NOT have access to the restroom. Please use public restrooms on shore PRIOR to boarding. Passengers will NOT be allowed to store food or drinks in the sailboat refrigerator. If you must keep things cold, please bring a small cooler. Passengers will NOT be allowed to store personal belongings or food below deck (in the cabin). Please minimize personal belongings as storage is very limited. Please consider NOT bringing a bunch of food and beverages. We suggest a small personal water bottle for hydration and, if necessary, individually wrapped snacks like granola bars.
    • COVID-19 ICE AND WATER POLICY - We will not be able to provide ice for charters this year. If you need ice, please plan to bring it. We will have bottle of water available. However, we would encourage you to bring your own water and help us reserve these bottles of water for emergency hydration.
    • Most travelers can participate
    • This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund
    • This is a private tour/activity. Only your group will participate
    • Face masks required for travelers in public areas
    • Face masks required for guides in public areas
    • Hand sanitizer available to travelers and staff
    • Regularly sanitized high-traffic areas
    • Gear/equipment sanitized between use
    • Guides required to regularly wash hands
    • Contactless payments for gratuities and add-ons
    • Refusal by anyone adhere to the COVID-19 policy may result in the immediate and non-refundable termination of the charter.
  • You can present either a paper or an electronic voucher for this activity.
  • For a full refund, cancel at least 24 hours in advance of the start date of the experience.



Age Req.


Fitness Req.


Group Size


Organised by Come Sailing, Inc.

Activity ID: V-46250P2

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