Recent Searches

Private Sunset Sail on Lake Michigan with Breathtaking Views of Chicago

Chicago, United States
Private Sunset Sail on Lake Michigan with Breathtaking Views of Chicago
Likely to Sell OutLikely to Sell Out

From USD427.28 per group (up to 6)

Lowest Price Guarantee

Select Date and Travellers

Number of travellers
1 traveller2 travellers3 travellers4 travellers5 travellers6 travellers
Free cancellation
Up to 24 hours in advance. Learn more
Loading available options...

Safety measures
icon2 hours  (approx.)
Mobile ticket
iconOffered in: English
Good for avoiding crowds


Soak up the views of Lake Michigan and the Chicago skyline with a 2-hour sailing tour. This private charter is completely customizable, giving you the chance to choose your music, route, and up to 5 additional guests. Sail into the sunset with your own drinks and snacks (refrigerator and ice on board) and your family or friends by your side.
  • Stunning views of Lake Michigan and the Chicago skyline
  • Private sailboat with US Coast Guard licensed captain
  • Small group ensures personalized experience
  • Choose your adventure by selecting your route
Saved to wishlist!
Professional captain licensed by the US Coast Guard
Use of Bluetooth speakers
All applicable taxes
Food and Drinks
Come Sailing, Inc. , Monroe Harbor, 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 BERNARD.

This activity will end right where it started.
  • Confirmation will be received at time of booking
  • 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.
  • CONSUMPTION OF ALCOHOL - Customers and guests may bring and consume reasonable amounts of alcoholic beverages within the bounds of Illinois State law.
  • 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.
  • 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.
  • 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.
  • ANIMALS ARE PROHIBITED - Unfortunately, we cannot accommodate animals of any type.
  • SWIMMING IS PROHIBITED - Swimming is not allowed on our Sunset Sails.
  • 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.
  • 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.
  • 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.
  • CLEANING FEES - Cleaning fees, if applicable, will be equivalent to the standard, full price of your charter.
  • 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.
  • 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 interchangeably throughout our website.
  • LATE ARRIVALS - The late arrival of customers and guests may result in a shortened charter sail without refund nor adjustment to price.
  • Not wheelchair accessible
  • Near public transportation
  • 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, 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.
  • 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, please let the captain know and they will be more than happy to wear face masks during your charter.
  • 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 appropriate social distances.
  • 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 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.
  • 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 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 to keep them cold. Food, beverage, and ice storage is limited to provided cooler. Please plan accordingly.
  • Most travellers can participate
  • 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.
  • This is a private tour/activity. Only your group will participate
  • OPERATED BY Come Sailing, Inc.
You can cancel up to 24 hours in advance of the experience for a full refund.
  • 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.
  • Any changes made less than 24 hours before the experience’s start time will not be accepted.
  • Cut-off times are based on the experience’s local time.
  • This experience requires good weather. If it’s cancelled due to poor weather, you’ll be offered a different date or a full refund.

Learn more about cancellations.

The answers provided below are based on answers previously given by the tour provider to customers’ questions.
What is the policy on sanitisation during Private Sunset Sail on Lake Michigan with Breathtaking Views of Chicago?
A:The policy on sanitisation is:

  • Hand sanitiser available to travellers and staff
See all safety measures taken by Private Sunset Sail on Lake Michigan with Breathtaking Views of Chicago.
What is the social distancing policy during Private Sunset Sail on Lake Michigan with Breathtaking Views of Chicago?
A:The policy on social distancing is:

  • Contactless payments for gratuities and add-ons
See all safety measures taken by Private Sunset Sail on Lake Michigan with Breathtaking Views of Chicago.

Traveller Photos

See More


14 reviews
3 stars
2 stars
1 star

Reviews by Viator travellers

Showing 1-8 of 14 reviews
Absolutely Amazing
, Aug. 2021
Highly recommend the sunset cruise. What a great way to view Chicago’s skyline! Friendly, informative Captain helped us decide on must see spots for the rest of our stay. Thank you.
Smoothie sailing
, Jul. 2021
Mike was awesome! It was my first time on a private sail with friends. We were comfortable, the sail was smooth and we had a great time. We didn’t want it to end.
Amazing experience!
, Jul. 2021
Great trip! I would recommend going for longer than 2 hours if you are able. We loved every moment and wished we had booked a longer tour.
icon Response from Host , Jul. 2021
Thanks Rebecca! It's really nice to hear that you had such a good time! We are working to make it easier for customers to book longer charters through TripAdvisor/Viator. Thank you! Capt. Mike
I could not stop smiling
, Jun. 2021
Captain Mike was awesome! So much fun and very knowledgeable. We had our own playlist playing the whole time and the views..... the best I’ve ever seen. We sipped wine and had the time of our lives. It was worth every penny.
icon Response from Host , Jul. 2021
Thank you so much Sarah_A! I love sailing and it's very rewarding for me to hear that my customers are loving it too! Thanks for sailing with us! - Capt. Mike
Lovely evening
, Jul. 2020
Perfect weather for a sunset cruise. The views of the skyline were amazing. The captain was informative and pleasant. My only complaint is that we were not informed ahead of time that the hull of the boat was not open due to Covid. That meant we could not use the bathroom. A bit of a problem.
icon Response from Host , Jul. 2020
Hi Kim! Thanks for sailing with us! I'm very glad you enjoyed the sailing but am sorry about the miscommunications regarding restricted access to the cabin below. I will check the product description and update as necessary to be sure people are aware of this COVID-19 related restriction. Thanks for pointing it out. See you on the water! Capt. Mike
Spectacular birthday celebration
, Jul. 2020
It was truly the best choice to do something different, special, and romantic to celebrate my Wife's birthday. We recently moved to Chicago and was the first time we saw the city from the inner lake. The views and sunset were truly spectacular. Captain Mike was quite friendly and professional. We felt quite safe under the circumstances.
Highest level sailboat experience!
, Jul. 2020
The captain was ready for us when we arrived. He was very informative. Great experience from beginning to end!
Sunset cruising
, May 2019
Cpt. Mike took us out in his boat for sunset, it was fantastic and very relaxed. I would highly recommend him and willl definitely do this again when we have our next visitors to Chicago.

Compare Similar Experiences

Private Sunset Sail on Lake Michigan with Breathtaking Views of Chicago
Likely to Sell Out
Private Sunset Sail on Lake Michigan with Breathtaking Views of Chicago


2 hours

Free Cancellation



2 hours

Free Cancellation



2 hours 30 minutes

Free Cancellation



3 hours

Free Cancellation



3 hours

Free Cancellation



3 hours

Free Cancellation



40 minutes

Free Cancellation



3 hours

Free Cancellation



1 hour 30 minutes

Free Cancellation


Explore Similar Things to Do