Frequently Asked Questions

How do I get to Chicago Sailing in Belmont Harbor?

Driving Directions from the North, Northwest, or West

Take Irving Park Rd (4000 North) East all the way to the lake.

After you pass under Lake shore Drive turn RIGHT and follow Recreation Drive South for .6 miles. After you have passed TWO consecutive stop signs and a large brown brick building (on your right), continue for 20 yds. Take your first parking opportunity after the pay gate. Chicago Sailing is immediately WEST of you, on B-Dock. Look for our houseboat/office at the head of the dock, flying a banner and flag.

Driving Directions from the South, Southwest, or West.
Take your first convenient opportunity to get on Northbound Lakeshore Drive (no later than Belmont Ave). Exit Lakeshore Drive at the Recreation Drive Exit (~3400 North) and take an immediate RIGHT at the stop sign. Continue through the next immediate stop sign and past a large brown brick building (on your right). Continue for 20 yds. Take your first parking opportunity after the pay gate. Chicago Sailing is immediately WEST of you, on B-Dock. Look for our houseboat/office at the head of the dock, flying a banner and flag.

Important Notes:
1. Chicago Sailing is located at the NORTH end of Belmont Harbor. We are not accessible from the Belmont Avenue exit.
2. The large brown brick building on your Right as you approach Chicago Sailing is the HARBOR OFFICE, NOT our facility.
3. Usually there is ample parking immediately adjacent to our facilities. There is an $11/day parking fee. The parking just north of the brown brick building is also $11/day. For more details on parking option, visit our directions page.
4. Traffic and parking can experience delays on weekends and on Cub game days. Consider public transportation, walking or cycling at such times.

Public Transportation
The “L” Train RED LINE to the Addison Station.
Either walk or take the bus East (away from Wrigley Field) Cross under Lake Shore Dr at the Addison Avenue pedestrian underpass. After crossing, continue South until you have passed across the bike path. Keep the boats and harbor on your right-hand side and pass beyond the brick building. Chicago Sailing is on the first dock after the brick building. Look for our houseboat/office at the head of the dock, flying a banner and flag.

How do I get to Chicago Sailing in Waukegan Harbor?

By Car

Once you have arrived in Waukegan, IL take Grand Ave east, over 137 and the train tracks.

At the stop sign, turn right onto Pershing Rd. At the next stop sign, turn left onto Clayton St. Turn right after one block onto N Harbor Pl. Park anywhere. Chicago Sailing's boats are located at the far north ends of docks A and C. The dock entrance is located by the Hotdog and Ice Cream stands.

By Metra Train
Take the Union Pacific/North Line to Waukegan. Upon arrival in Waukegan, cross over the tracks to head towards the lake (east). Walk along E Madison St (approximately 5 - 10 minutes) until you reach the car turn around. Chicago Sailing's boats are located at the far north ends of docks A and C. The dock entrance is located by the Hotdog and Ice Cream stands.

Important Notes:
1. Chicago Sailing is located in the North Harbor facility of Waukegan Harbor. We are not accessible from the South Harbor.
2. Usually there is ample parking immediately adjacent to our facilities. Parking is free.

When and where can I pick up my course materials?
You may pick up your book in Belmont Harbor at any time the office is open. Our office opens when our season opens and the hours are Monday - Friday 9 am - 6 pm and weekends from 8 am - 7 pm. We recommend calling ahead on days with inclement weather or heavy winds as our office will occasionally close early due to weather.

If you are taking classes with us in Waukegan Harbor, please discuss options for picking up your book with our reservations staff. They can be reached at 773.871.7245.

What time should I arrive for classes?
Punctuality, especially on your first day, is important for many reasons. First, you may experience unexpected delays with traffic or parking. Second, there are important registration forms and procedures that must be completed in order for the class to begin on time. Finally, an early arrival gives you ample time to meet your instructor and fellow students. It is also a good time for a last minute restroom visit. We recommend arriving about 30min prior to your first class and about 10 min before each subsequent class.

What do I wear, what should I bring?
The first rule of sailing is Be Prepared. All Chicagoans know how quickly the weather can change. No matter what the temperature onshore is, it will feel at least 10 degrees cooler once you are out on Lake Michigan.

We Highly Recommend that you dress in layers that are capable of protecting you from chilly conditions or sun. Your unneeded clothing can always be stowed aboard the boat. A windbreaker/raincoat is advisable in all but mid-summer conditions. Fleece clothing is more comfortable than cotton.

Don’t forget the sun protection (UV block, lip balm, hats, visor, etc), water, and snacks. We sell bottled water at our dock.

Leave your textbook ashore. You will not need it and it may get wet and destroyed.


Will there be a place to store my extra gear on-board?
On our J/22s and J/24s there is a small cabin below decks, where your gear can be stowed. While this area is usually dry, we recommend that you lock valuable items in your auto trunk. Keep at least one cell phone aboard the vessel in a secure, dry location. We have complimentary watertight bags available at our dock.


What kind of shoes can I wear, can I go barefoot?
For your safety and comfort, Chicago Sailing requires that you wear shoes during all sailing lessons. While boat shoes are not mandatory, any footwear must provide sound footing and must have non-marking soles (to tell if your soles are non-marking scuff your foot on a wood or tile floor). Please do not wear flip flops or high heels. If you are uncertain about the appropriateness of your shoes, please call prior to arrival. Boat shoes are available at West Marine (local store), Boater’s World, DSW Shoe Warehouse, and other marine stores. Recently, we have seen appropriate shoes at both Target and Payless Shoe Source.

Are food and drinks allowed?
You are welcome to bring your own food and drink as long as it is appropriately consumed and cared for. While alcoholic beverages are not allowed during class activities, you may enjoy them responsibly during rentals and charters. It is wise to stay hydrated with non-alcoholic beverages. We offer bottled water for sale at our facility.

Food is also encouraged and should be confined to items that require little or no on-board preparation. Trail mix bars and small packaged food works the best to keep your energy up though out the whole class. Class participants often enjoy taking turns bringing treats for the entire group.

Any food and beverages that you bring on board for your sail must be disposed of at the end of your reservation. Trash bags can be obtained from the staff in our office and there is a large trash can located on the stern (rear) of our houseboat headquarters.

How do we handle inclement weather? Who can I call?
Chicago Sailing takes safety seriously, including weather related hazards. To that end we reserve the exclusive right to determine safe sailing conditions. Expect that your class, rental or charter will take place as scheduled unless you hear otherwise from Chicago Sailing. Weather in Chicago can change very quickly and exhibit many different conditions throughout a 12-hour period. You are always welcome to call our Reservations Staff at 773.871.7245 on the day of your sail to obtain an update in regards to the weather.

The first day of class will never be canceled, as there is much material that can be taught at the dock regardless of weather conditions.

How much advance notice will you give me for any cancellations?
Weather in Chicago can be suddenly changeable. For this reason we will usually not make a final cancellation or postponement determination until just prior to a scheduled event. Plan to arrive on time unless you are contacted by Chicago Sailing. If you have any weather concerns please call us at 773.871.7245.


How are weather-related class cancellations handled?
Chicago Sailing, at its sole discretion, may shorten or cancel a scheduled class. This may require that a make-up class be scheduled for a time established by the Chicago Sailing instructor and the class majority.

What happens if I have to miss a class?
Chicago Sailing strongly recommends that you plan to attend all scheduled classes. If an unexpected emergency results in your absence, you must promptly make up the missed classwork via private lessons if you wish to complete the course. There is an additional charge for private lessons.

Can I change my class time? Will there be a fee?
Click here for full policy or see below:

Instructional Cancellation:
Courses beginning 14+ days: Customer will receive a full credit less a $100 administrative fee.
Courses beginning 7 - 14 days: Customer will receive a full credit less a $200 administrative fee.
All other cancellations: NO credit.
Instructional Rescheduling:
For courses beginning in 7+ days: There will be a $50 administration fee.
All others: If Chicago Sailing can fill your spot there will be a $50 administration fee. If not there will be no refund.

What is the difference between US SAILING CERTIFICATION and being qualified to rent boats from Chicago Sailing?
After a successful completion of the Basic 101 class you will receive graduation papers that attest to your achievement and your provisional qualification to rent our J/22 sailboats. US SAILING Basic Keelboat Certification is obtained by successfully completing Advanced Sailing 161 and passing the qualification exam. This certification is recognized throughout the world’s sailing community as the premier standard of sailing achievement.

How much does certification cost?
The Certification fee of $100 is included in the cost of the Advanced Sailing 161 course. It includes an official logbook, certification of accomplishment and a one-year membership in US Sailing.

Alternatively you can schedule a 2-hour private lesson with one of our instructors at the regular rate and we will administer the certification exam for an additional $100 certification fee.

Should I tip the staff? If so, what is appropriate?
Tipping is purely optional and always appreciated by our staff. While we are reticent to suggest an appropriate gratuity, instructors commonly receive tips in the range of $10- $50 range for exemplary service. Tips have been in many forms from game tickets, food, bikes and even air conditioners! If you experienced service below your expectations, please inform our management team so that we can discretely incorporate your suggestions into that instructor’s further training.

Tips for our captains are greatly appreciated. We recommend tipping between 10 and 20%. You can tip the captain in cash or add it to your payment transaction when you check out with our Reservations Staff.

If you have additional questions, please feel free to contact us .