Tours and Tickets
Private Lake Michigan Sailing Charter and Sightseeing Chicago Skyline Cruise

Private Lake Michigan Sailing Charter and Sightseeing Chicago Skyline Cruise

By Come Sailing, Inc.
Enjoy a private two and a half hour sailing experience for up to four 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.
from
€411.82
per group (up to 4)
from
€411.82
per group (up to 4)

Lowest price guaranteeReserve now & pay laterFree cancellation

Ages 0-120
Duration: 2h
Start time: Check availability
Mobile ticket
English


  • Use of Bluetooth Speakers
  • Professional US Coast Guard licensed captain
  • All applicable taxes
  • Entry/Admission - Chicago
What's not included
  • Food and drinks
  • Parking
  • Gratuities


Departure details
  • Come Sailing, 400 E Monroe St, Chicago, IL 60603, USA From the northeast corner of Lake Shore Dr. and Monroe St. follow the lakefront trail to the north and continue along the harbor’s edge as the trail bends to the east. Our boat will meet you along the Monroe Harbor wall east of the cement pier (aka the pump out dock). Our boat’s name is DRUID.
Return details
  • Returns to original departure point

  • Near public transportation
  • Not wheelchair accessible
If you have questions about accessibility, we’d be happy to help. Just call the number below and reference the product code: 46250P9

  • Confirmation will be received at time of booking
  • 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 Prevention, Illinois Department of Public Health, Cook County Department of Public Health, and Chicago Department of Public Health.
  • 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 and the assessment of a cleaning fee.
  • COVID-19 FOOD, WATER, AND ICE - 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 to keep them cold. Food, beverage, and ice storage is limited to provided cooler. Please plan accordingly.
  • COVID-19 SOCIAL DISTANCING - 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 appropriate social distances.
  • 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. There is a restroom on board each boat. However, the restrooms are small, and toilets on a boat do NOT work the same way your toilets work at home. Please ask the captain and crew before using the restroom. We strongly encourage you to use the public restrooms on shore prior to boarding.
  • COVID-19 FACE MASKS ARE OPTINAL - 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, please let the captain know and they will be more than happy to wear face masks during your charter.
  • COVID-19 SICK PEOPLE SHOULD STAY AT HOME - 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 not feeling well. SYMPTOMATIC – If, in the last 5 days, you have experiences symptoms related to COVID-19, the flu, or any other potentially contagious disease.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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 termination of your charter.
  • 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 disposals. Please do NOT treat our sinks like you treat your kitchen sink. They are NOT the same.
  • 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 in a non-refundable, early termination 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.
  • SWIMMING IS PROHIBITED - Swimming is not allowed on this sailing charter.
  • LATE ARRIVALS - The late arrival of customers and guests may result in a shortened charter sail without refund nor adjustment to price.
  • 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 the below deck cabin area of the sailboat, including the “head”/bathroom.
  • 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 agreed upon.
  • 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, successors, assignees and affiliates, and their respective employees, officers, directors, shareholders, and representatives the right and permission to use such film, photographs, and recordings of your 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 that minor child.
  • Most travellers can participate
  • This experience requires good weather. If it’s cancelled 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

  • For a full refund, cancel at least 24 hours in advance of the start date of the experience.

Which attractions will I visit with Private Lake Michigan Sailing Charter and Sightseeing Chicago Skyline Cruise?
How much is Private Lake Michigan Sailing Charter and Sightseeing Chicago Skyline Cruise?
Private Lake Michigan Sailing Charter and Sightseeing Chicago Skyline Cruise price starts from €398.72. Discover and book Private Lake Michigan Sailing Charter and Sightseeing Chicago Skyline Cruise on Tripadvisor
What is the Private Lake Michigan Sailing Charter and Sightseeing Chicago Skyline Cruise cancellation policy?
Private Lake Michigan Sailing Charter and Sightseeing Chicago Skyline Cruise cancellation policy: For a full refund, cancel at least 24 hours in advance of the start date of the experience. Discover and book Private Lake Michigan Sailing Charter and Sightseeing Chicago Skyline Cruise on Tripadvisor
Which company provides Private Lake Michigan Sailing Charter and Sightseeing Chicago Skyline Cruise?
Private Lake Michigan Sailing Charter and Sightseeing Chicago Skyline Cruise is hosted by Come Sailing, Inc.. Read reviews, discover additonal experiences or contact Come Sailing, Inc. on Tripadvisor. Discover and book Private Lake Michigan Sailing Charter and Sightseeing Chicago Skyline Cruise on Tripadvisor

If you have questions about this tour or need help making your booking, we’d be happy to help. Just call the number below and reference the product code: 46250P9

Itinerary
  • You'll start at
    Come Sailing
    400 E Monroe St, Chicago, IL 60603, USA
    From the northeast corner of Lake Shore Dr. and Monroe St. follow the lakefront trail to the north and continue along the harbor’s edge as the trail bends to the east. Our boat will meet you along the Monroe Harbor wall east of the cement pier (aka the pump out dock). Our boat’s name is DRUID.
    See address & details
  • 1
    Come Sailing
    Stop: 2 hours - Admission included
    See details
  • 2
    Buckingham Fountain
    See details
  • 3
    Shedd Aquarium
    See details
  • 4
    Adler Planetarium
    See details
  • 5
    Soldier Field
    See details
  • 6
    Navy Pier
    See details
  • 7
    Chicago Skyline
    See details
  • You'll return to the starting point
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About the operator

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

johnpD984NB
johnpD984NB
00
Fun on the lake, and great views of the city skyline
Hard to ask for a better day. My favorite part was that there was no messing around...just as soon as we motored o
erinheberling
erinheberling
00
Captain Ulysses was the BEST!
We had a great time sailing with Captain Ulysses. He was very knowledgeable and we had a great time. Would definite
staceybY98WU
staceybY98WU
00
Relaxing Sail; Beautiful Views
Our 2-hour sail was the perfect escape from the noise of the city. The boat was comfortable and clean. We were give
563shayb
563shayb
00
A must do sailing adventure!
The sunset sail was positively amazing! Captain Mike made the sail even better! We will definitely do again.
carolhP1497UD
carolhP1497UD
00
Gem of Chicago!
Captain Mike and the entire Come Sailing experience was fabulous! Great way in which to see the beauty that is Chi
jaycie2017
jaycie2017
00
Leisurely sailing the gorgeous lakeshore
We had a wonderful time. The weather was perfect and the views of the Chicago skyline are always magnificent. We ac
CarlaMarlaMinky
CarlaMarlaMinky
00
Great Experience!
The four of us went out with Captain Mike and we had a wonderful time; he is obviously extremely skilled at sailing
Griffith_JP
Griffith_JP
00
July Jackpot Sail
We had an excellent experience with Captain Mike on the Druid. The sail was very smooth and the boat is even more b
sana k
sana k
00
The trip was very awesome
A beautiful trip that l and myself enjoyed it so much. l recommend people to try it. Captain Michael was very nice
Carrie_R_T_NOLA
Carrie_R_T_NOLA
00
Highlight of our trip!
Relaxing and beautiful to see Chicago from the lake on a sailboat, and Captain Mike was very friendly and informati
kathrynsC2972IY
kathrynsC2972IY
00
Great experience
It was a beautiful afternoon on the water. Captain Ulysses was great to sail with and kind about an unexpectedly se
RavvenaTravel
RavvenaTravel
00
SEE CHICAGO FROM THE WATER IN RELAXATION
We were recommended a sailboat experience on the lake and it was truly exceptional. My brother-in-law and I were in
Sammie P
Sammie P
00
Fantastic!
I cannot reccomend this enough. Magical, relaxing, beautiful and just a blast! Captian Mike was awesome! I would
811cheriek
811cheriek
00
Sunset charter with Captain Mike is an unforgettable experience!
Captain Mike was wonderful! This was our first sailing adventure and it could not have been a better experience. He
ChefShawn1983
ChefShawn1983
00
Honeymoon Delight
Captain Mike, Helped make our honeymoon so special. My wife got to take the helm so I think she's now a real life
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2023 Private Lake Michigan Sailing Charter and Sightseeing Chicago Skyline Cruise