Private Sunset Sail on Lake Michigan with Breathtaking Views of Chicago

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From $483.96

16 reviews   (4.94)

Price varies by group size

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Pricing Info:

Duration: 2 hours

Departs: Chicago, Chicago

Ticket Type: Mobile or paper ticket accepted

Free cancellation

Up to 24 hours in advance.

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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.

What's Included

All applicable taxes

Professional captain licensed by the US Coast Guard

What's Not Included

Food and Drinks



Traveler Information

  • TRAVELER: Age: 0 - 99

Additional Info

  • BOOKING ERRORS - We reserve the right to cancel reservations that are the result of incorrect pricing/availability due to malicious acts or software/website errors.
  • CONSENT TO BE FILMED/PHOTOGRAPHED - 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, su
  • Contactless payments for gratuities and add-ons
  • COVID-19 FACE MASKS ARE OPTIONAL - MASK FREE SAILING IS HERE! New for 2022, face masks are OPTIONAL. Wear them or not, the choice is yours. Our captains and crew are not required to wear face masks. However, if it would make you feel more comfortable, ple
  • COVID-19 POLICY UPDATES AND CHANGES - The above policies are subject to change without notice in response to changes in status of the COVID-19 pandemic and in order to comply with new or changing guidance from the Centers for Disease Control and Preventio
  • COVID-19 SOCIAL DISTANCING POLICY - This is a private charter for you and your guests only. Social distancing is your responsibility and at your discretion within your group. There is plenty of space on board our sailboats to spread out and maintain appro
  • CUSTOMER/GUEST BEHAVIOR - 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
  • GALLEY STOVE AND SINK - The galley stove onboard our sailboat is NOT for use by customers. The sinks on board our boats drain directly into the lake and are NOT intended for food prep nor for disposing of unwanted items. None of the sinks have garbage dis
  • Hand sanitiser available to travellers and staff
  • NO GLASS ON BOARD - Glass containers are prohibited. Please do not bring them. Wine and Champagne bottle are permitted as long as they remain secure in a protective container during charter. Please bring plastic cups for drinking.
  • Public transportation options are available nearby
  • See Additional Info section for more COVID related details.
  • SWIMMING IS PROHIBITED - Swimming is not allowed on our Sunset Sails.
  • WEAPONS ARE STRICTLY PROHIBITED - Weapons on any kind are strictly prohibited! Guns, knives, or weapons of any kind are NOT allowed on board our vessels at any time. Bringing any of these prohibited items aboard may result in a non-refundable, early termi
  • ANIMALS ARE PROHIBITED - Unfortunately, we cannot accommodate animals of any type.
  • CLEANING FEES - Cleaning fees, if applicable, will be equivalent to the standard, full price of your charter.
  • CONSUMPTION OF ALCOHOL - Customers and guests may bring and consume reasonable amounts of alcoholic beverages within the bounds of Illinois State law.
  • COVID-19 ACCESS TO CABIN AND RESTROOMS - The fun is up on deck sailing! Not hanging out below deck in the cabin! So, please minimize your time below deck in the cabin. We also ask that no more than one person goes down below into the cabin at a time. Ther
  • COVID-19 FOOD, WATER, AND ICE POLICY - We will have bottles of water available. However, we encourage you to bring your own beverages and help us reserve our water for emergency hydration. We will provide a small cooler in which passengers may store items
  • COVID-19 SICK PEOPLE SHOULD STAY AT HOME POLICY - All passengers are required to self-diagnose their health status before boarding and let us know if they are not feeling well. PLEASE STAY AT HOME IF ANY OF THESE CONDITION APPLY: SICK – If you are sick or
  • COVID-19 vaccination required for guides
  • FOOD AND BEVERAGE - 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.
  • GIFT CERTIFICATES/VOUCHERS - Gift Certificates may not be redeemed for cash. Gift certificates may be used to purchase products and services offered by Come Sailing, Inc. The terms “gift voucher” and “gift certificate” have the same meaning and are used i
  • LATE ARRIVALS - The late arrival of customers and guests may result in a shortened charter sail without refund nor adjustment to price.
  • NO SMOKING - All charters 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 an
  • SEASICKNESS/MOTION SICKNESS - 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 t
  • Suitable for all physical fitness levels
  • TERMINATION OF 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. A refund will be offered if rescheduling cannot be a

Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

  • For a full refund, you must cancel at least 24 hours before the experience’s start time.
  • If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
  • This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.

What To Expect

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.

2 hours • Admission Ticket Included

Buckingham Fountain
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, Buckingham fountain is not related to 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.

• Admission Ticket Free

Shedd Aquarium
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.

• Admission Ticket Free

Adler Planetarium
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.

• Admission Ticket Free

Soldier Field
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.

• Admission Ticket Free

Navy Pier
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!

• Admission Ticket Free

Chicago Skyline
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.

• Admission Ticket Free

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