moderate
2–3 hours
Suitable for those with average fitness; some standing and light movement on deck required.
Discover Chicago’s skyline from the water on a weekday afternoon sailing tour across Lake Michigan. Perfect for city explorers looking to combine urban sightseeing with a refreshing lakeside outdoor adventure.
Starting at $400 | 2.5 Hour Private Charter | Up to 6 Guests
Experience a unique weekday afternoon sailing adventure with ChicaGo By Boat! Perfect for corporate outings or a relaxing staycation, this private charter accommodates up to six passengers. Enjoy the scenic views while bringing your own food and pre-mixed cocktails, all under the guidance of a licensed captain.
Thanks for considering ChicaGo By Boat, and prepare for your Weekday Afternoon Sailing Private boat charter--they're great for corporate outings or even just a staycation!
What to bring:
Up to six passengers regardless of age
Food and beverage (food should not need to be plated and any cocktails must be pre-mixed)
Activity and weather appropriate clothing:
Current Conditions
Forecast
Gratuity--Please tip your Captain & Crew
What NOT to bring:
Cigarettes, cigars, etc.
Denim/jean clothing of any type
High Heeled footwear and/or footwear with marking soles
Liquor bottles (cocktails must be pre-mixed)
Recreation Drugs/Controlled Substances
Red wine
Rolling Coolers
Strollers
Sorry, but if you are wearing any of the clothing items listed above, you will not be permitted to board the boat. Items listed above can irreparably damage the boat so we appreciate your cooperation.
What's on board:
USCG licensed Captain
All legally required safety equipment,
Marine head (bathroom)
Refrigerator
Plates, cups, and utensils
Bluetooth compatible Bose Stereo
Cushioned seating in cockpit
Patagonia rain jackets and fleece
POLICIES:
Not complying with the policies outlined below will result in the cancellation or termination of your charter with no refund, credit, or proration of the original purchase price, and may result in legal action as necessary.
Alcohol:
ChicaGo By Boat LLC is not authorized to sell alcohol. Passengers may bring their own alcohol to consume at their own risk. However, if any guest displays signs of being overly intoxicated before or during the charter, ChicaGo By Boat LLC, will terminate the charter with no refund, credit, or proration of the original purchase price.
Cancellations:
If we, ChicaGo By Boat LLC, cancel a charter for any reason, the original charterer will receive a full refund of the original amount paid to the original form of payment.
All changes and cancellations to reservations must be made by the original charterer in writing via email by responding to the original confirmation email.
The original charterer can make changes to, or cancel, their reservation up to seven days of the scheduled departure time and receive a full refund of the original amount paid to the original form of payment.
Any reservation canceled within seven days of the scheduled departure time will forfeit 33% of the original charter price and the associated taxes fees.
Reservations made with purchased codes can not be changed or canceled by the original charterer. If we, ChicaGo By Boat LLC, cancel a charter made with a purchased code, it can be rebooked before October 31st of the same year.
Charters are for the period of time that the booking was created for, NOT the duration that the booking was created for. For our passengers' safety and our liability, we board the vessel once all passengers have arrived for the charter. If any or all passengers are late, or do not arrive for the charter by the scheduled departure time, ChicaGo By Boat LLC is not obligated to extend the charter, prorate the original purchase price, or issue any refund.
A note about cancellations:
As protocol, we only sail if we are confident that our guests will be safe and comfortable. But, ChicaGo By Boat is a seasonal, weather dependent business, so we can not cancel charters based on forecasts. We only cancel charters based on actual weather. To be respectful of our guests' time, and the associated costs of traveling to the harbor, we try to cancel charters a minimum of two hours before the scheduled departure time. We would prefer that our guests have no experience with us than have a negative one, and sometimes the positive experience is the one you don't have at all. We are ok with you being upset with us for cancelling your charter. We are not ok with you being upset with us because of an avoidable unsafe or uncomfortable experience.
Capacity:
Our vessels are registered and insured to carry a maximum of six passengers regardless of age.
Children:
Children are welcome aboard on weekdays and are counted as passengers regardless of age. Children ages twelve-years-old and under must be accompanied by adults in a 1:1 ratio. In excess of state and Federal law, Children ages twelve-years-old and under must wear a personal flotation device (PFD) during their entire time aboard. ChicaGo By Boat LLC can and will provide a USCG approved PFD to any person on board.
Compliance:
ChicaGo By Boat LLC and its subsidiaries are registered and licensed as passenger vessels with the Illinois Department of Natural Resources and/or are Documented with the United States Coast Guard and maintain commercial insurance policies. All of our named operators meet or exceed the credentialing requirements of the United States Coast Guard.
Conduct:
No passenger may conduct themselves in such a way that will result in injury to any person on board, damage to the vessel, or damage to the reputation of ChicaGo By Boat LLC. If you and/or your guests do so, the charter will be terminated with no refund, credit, or proration of the original purchase price, and ChicaGo By Boat LLC will pursue legal action as necessary.
Damage:
If you and/or your guests cause damage or an excessive mess of the boat, you and/or your guest will be compensable for restorative measures.
Dress Code:
Passengers should wear weather and activity appropriate clothing. ChicaGo By Boat LLC does not allow denim/jean clothing of any type or color, high heeled footwear, or footwear with marking soles.
Fraud:
If you attempt to defraud ChicaGo By Boat LLC, ChicaGo By Boat LLC will purse legal action as necessary.
Marine Head (Bathroom):
There is a marine head (bathroom) onboard, and it is designed for emergency use. Due to boat traffic, the physics of sailing, or environmental conditions, its usage is not guaranteed.
Payment:
Payment is due at the time of booking.
All payments must be made online through our third party reservation system.
ChicaGo By Boat LLC will not accept payments verbally via the phone or through electronic communication.
Government issued identification for the original charterer and the credit card used to create the reservation must be presented in person before any passenger can board the vessel.
Physical Ability:
We are not accessible. All guests need to be able-bodied so that they can board and de-board the vessel unassisted.
There will be delayed access to advanced medical while under weigh which could be detrimental to the health and safety of passengers with preexisting medical conditions.
All passengers must be able to hear, understand, and comply with any directions or information given by agents of ChicaGo By Boat LLC.
Prohibited Items:
Cigarettes, cigars, etc.
Denim/jean clothing of any type
High Heeled footwear and/or footwear with marking soles
Liquor bottles (cocktails must be pre-mixed)
Recreation Drugs/Controlled Substances
Red wine
Rolling Coolers
Strollers
Purchased Codes, e.g. Groupon & Livingsocial Vouchers:
Recreational Drugs/Controlled Substances:
Illegal and recreational drugs are explicitly banned in any form. If consumption or possession of recreational drugs/controlled substances is suspected, ChicaGo By Boat LLC will end the charter with no refund, credit, or proration of the original purchase price, and ChicaGo By Boat LLC will pursue legal action as necessary.
Smoking:
ChicaGo By Boat LLC can not allow smoking on board any vessel. Passengers can use electronic cigarettes and vaporizers.
Swimming:
Our insurance policy does not provide coverage for swimming, so we do not allow any passenger to swim.
2023 Liability Waiver and Release Agreement | ChicaGo By Boat LLC
Lake Michigan’s winds can change quickly, so check the forecast before heading out to dress appropriately.
Deck surfaces can get slick, especially when wet; proper footwear improves safety.
Afternoon lake breezes can be cooler than onshore temperatures, even in summer.
Allow extra time for parking and boarding to ensure a smooth start to your sailing adventure.
Chicago’s maritime history dates back to the city’s founding, linking commerce and recreation on Lake Michigan for over 150 years.
Chicago By Boat supports clean water initiatives and adheres to environmental regulations to minimize impact on Lake Michigan's ecosystem.
Keeps you warm and shielded from afternoon lake breezes during cooler spring days.
spring specific
Protects your eyes from the sun’s glare on the water for a more comfortable trip.
summer specific
Allows for quick adjustments as temperatures drop and winds pick up in autumn.
fall specific
Useful if sailing extends into colder seasons or unexpectedly cool afternoons.
winter specific