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Lake Michigan Sunset Sail with Breathtaking Views of Chicago

Likely To Sell Out
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US$ 117.07
2 travellers
You'll start at
Come Sailing, Inc.
Monroe Harbor, Chicago, IL 60603, USAFrom the intersection of Monroe St. and Lake Shore Dr., walk northeast to the water’s edge and continue walking along the north side of the harbor as it curves first to the east and then again to the north. Our boat will meet you at spot #4 in the yellow stripe along the “Monroe Charter Wall”.
See address & details
  • 1
    Come Sailing, Inc.
    Stop: 2 hours - Admission included
    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.
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    Pass by Buckingham Fountain
    Pass by Shedd Aquarium
    Pass by Adler Planetarium
    Pass by Soldier Field
    Pass by Navy Pier
    Pass by Chicago Skyline
You'll return to the starting point
Important Information
Departure Point
Come Sailing, Inc., Monroe Harbor, Chicago, IL 60603, USA
Return Details
Returns to original departure point
  • Professional US Coast Guard licensed captain
  • Ice box / refrigerator on board
  • Restroom on board
  • Use of Bluetooth speakers
  • All applicable taxes
  • Entry/Admission - Come Sailing, Inc.
  • Gratuities
  • Food and drinks
  • Parking
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Additional Info
  • Confirmation will be received at time of booking
  • Not wheelchair accessible
  • Near public transportation
  • Most travelers can participate
  • Lake Michigan Sunset Sail with Breathtaking Views of Chicago
  • 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.
  • Any person wishing to swim during the charter will be required to sign a waiver and release upon boarding the sailboat. Swimming will be allowed on the morning and day sail charters only and will be at the captain’s discretion.
  • 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.
  • 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 experience requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund
  • This tour/activity will have a maximum of 6 travelers
Cancellation Policy
For a full refund, cancel at least 24 hours in advance of the start date of the experience.


About the operator

This tour has not yet been reviewed, but you can read what other travellers have to say about this operator.

By: Come Sailing, Inc.
Atlanta, Georgia
Great time on the lake
Thank you Mike for the nice ride on your beautiful boat. We had such a great time and fun ! Appreciate that we
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Chicago, Illinois
No better way to see Chicago!
Come Sailing and Captain Mike are absolutely the best in Chicago. The skyline that has no equal can only be best
Read more
Bobby G
Chicago, Illinois
Best way to sightsee in Chicago, in private!
Sailing on beautiful Lake Michigan offers an experience not to be missed! ‘Come Sailing Chicago’ offers a Catalina
Read more
Kim V
Carmel, Indiana
Go Sailing
Great tour! Fun experience. Excellent city views. Captain Mike was awesome. We lucked out and scored amazing
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Los Angeles, California
Front Row "Seats" for the Fireworks
I don't know where to begin in writing this review because every part of the evening was purely magical! First of
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Lucille S
Sailing into the sunset...
Great tour. There were only four of us although the reservations can accommodate 6 people. Captain Mike very nice
Read more
Chicago, Illinois
Incredible Sunset Sail!
This was my second experience with Come Sailing and Captain Mike, and it was an even BETTER experience than the
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Colin M
Truly brilliant and unforgettable trip
This is the #1 must do thing in Chicago. In relative terms it represents fantastic value. Captain Mike was
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New York City, New York
The Perfect Sail
Can't say enough good things about this experience, from start to finish it was A+++. The booking process, the
Read more
Peter C
Awesome time sailing!
Had an amazing time sailing with Captain Mike. Great boat and Capt Mike went out of his way to make sure we all
Read more
Key Details
  • Duration: 2h
  • Mobile Ticket Accepted
  • Instant confirmation
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