Our family had a great day sailing yesterday. Bumblebee was a fantastic vessel and Captain Alan was an amazing host and Pilot. The views of Chicago’s skyline are always breath taking. A stop in them ‘play pen’ for a swim was refreshing and great for photo ops. Everyone is ready to book our next trip already.A few years back I also took sailing lessons here and they were great. I learned a lot and built up my confidence and skills. That said it has been a few years so it was great having an experienced Captain like Alan hosting us.

I visit the US a few times a year. Had a good experience last summer in Seattle chartered a bareboat. Since Id one weekend off in Chicago, I thought itd be an equally good experience to charter one and sail on Lake Michigan. Booked on a Hunter, but very disappointed:1. No details about the boat or equipments; shall post them online. When I arrived, the Hunters were actually quite old; its ok to be an old boat, but the equipments were not well maintained.2. Staffs were very friendly, but thats not enough, we are talking about sailing, it means safety. They were not very experienced with sailing or the sailboats. The checkout procedures were too casual. There were no emergency procedures, location of fire distinguishers, equipments I might need in case of an emergency, etc..3. Visited two Hunters: one with engine problem, couldnt restart. One was even worse, found 4-inch water at the keel bolts compartment; no one could tell me where the water came from. When the manager turned on the fresh water pump, water started to go into that compartment; that means fresh water pipes leakage!So, they refunded me at the office. While I was being refunded, they let another party to leave the berth with the same Hunter.It looks like a good business because it was a busy day for them. To maintain the reputation and quality, they should improve:- Online information about the boats- Checkout procedures, particularly in safety and in case of an emergency- Show your maintenance records to your customersHope to get on board again, and sail happily and safely on Lake Michigan.

Great, personable, and knowledgeable staff. Would recommend to new and veteran sailors alike.

An amazing experience charting a boat for the afternoon. Took out 7 coworkers and had a great time. Captain Alan took great care of us and the office staff was amazing. Highly recommend!

Kids did sailing camp there, had a great time

Thinking back, I should have read the reviews. The boat I took was not maintained AND NOT SAFE! The check out was a joke. Our departure was delayed because the dude was busy eating chicken... Part of the rigging failed when I was 5 miles off shore and I had to fix it on the fly. Thank you God nothing was really serious. Did anybody ask me at the end how the boat was? Or just thanked me for business? No. But they had to be rude when I returned. Note to myself: do NOT sail a boat cover with spider web... No, it is not a joke...

If you want to rent a boat in Chicago this is a fair place to consider. The rates are reasonable, but I would not be overly enthusiastic about the dependability of the motors on their sailboats.On at least two occasions we had trouble with the motor.The first time, we had no trouble motoring out of the berth into the lake but as we were preparing to return to Chicago Sailing the motor would not start, we tried everything, nothing worked. Luckily there were 4 of us on board and someone suggested something that finally worked. On another occasion, we had no problem motoring out, but when we were motoring back, the engine just stopped. We tried everything we could to restart it and nothing worked. I see on this forum and on another forum, others customers have had concerns or problems too with their motors.

We had the most enjoyable experience EVER!! Graham was totally experienced and knowledgeable about Sailing and Chicago in general. I would recommend Chicago Sailing to anyone that wants to spend some time on Lake Michigan.

Just DONT ! Filthy Boats look and smell as if the interior has never ever been washed down. Life jackets are so filthy you dont want to touch. Sails tattered and worn (on Memorial Day weekend, beginning of the season). Insect infected boats with swarms of gnat like flying bugs from inside the boat cabin and sails. (no I dont mean those naturally out on the water). The smell of diesel is overwhelming in the cabin. This would put you off sailing altogether. Take your business elsewhere.

They were really friendly and the food arrangements were also good. They treated all the customers equally and respectable. Nice agency....

This was the worst Charter experience. The Boat. It was nasty. Clearly hasnt been cleaned in years. I was told the galley would be a nice place to make a snack. I wouldnt let food come any where near the galley unless you like food poisoning. And the bathroom. I was told by upgrading to the larger boat, I would have a bathroom. I had a toilet all right. A toilet that didnt work. Almost didnt have toilet paper. (I had to request it before we left the dock) and NO DOOR. I was the only female on the charter boat. I expect a door. So much for paying extra. After our three hour sail, we headed back to the dock to find that our engine wouldnt start. Even better, the face plate where you place the key, almost fell off in the captains hand when he was trying to turn the key. Now thats a quality boat. So stuck on a nasty boat, no working toilet, no privacy door, piece of ****, in the middle of Lake Michigan thanks to no engine. Then at the end of the ride, they had the nerve to charge full price for the charter. I tried to call them back to speak to the owner about my experience and request a refund of some sort and was NEVER called back. These guys are the cheapest in Chicago for charter boats, you get what you pay for.

Excellent instruction! I re-learned many things I had forgotten and had an excellent time sailing on the lake. Thank you!+GIL

Had great time sailing the j22 just wish the wind was better, but hey thats sailing right.

Perfect spot for daily sailboat rentals

The office staff, Emma and Chris, are friendly and helpful. Unfortumately, at least one of the boat captains is a little elitist jerk: arrogant, petty, unsafe and more like a little Captain Queeg with a complex. Sail Manhattan is a better name here. Not worth the $80/hour. Took out one of the J-boats cause my sailing partner was sick, wont do it again.

I rented multiple times from Chicago Sailing during the 2015 and 2016 season and I recommend them.Chicago Sailing offers a variety of services that I havent used, so I cant speak competently about those; what I can review is the boat rental service. I have an ASA bareboat certificate and I rent J/22 boats, acting as a skipper myself. I have always found that the Chicago Sailing boats were clean and well maintained when I rented them. Their J/22 boats are rigged very well, with lazy jacks, roller furling jibs and reefing lines permanently installed. The boats can easily be handled as rigged with a total crew of 2 and probably even single-handed (although sailing single-handed is not allowed by their rules). The motors are also well-maintained and they typically turn on easily and keep working reliably.Chicago sailing has a strong emphasis on safety, insisting on a per-year per-design checkout before you are allowed to rent from them. They also want you to be continuously reachable by cell-phone, and to contain your track within a 1NM x 2NM box. You are required to keep hatches and companionways closed while underway. All these restrictions are meaningful and I would expect the same from any establishment that cares about the safety of their renters.They also want you to get in and out of the harbor on dual power, i.e., with the mainsail up and the engine running. In my opinion, this requirement may at times complicate things rather than make them safer (because you are dousing the sails in the harbor, possibly within traffic) but I respect it and I comply.Some of their J/22s have stanchions and lifelines and some dont, so you have a choice which boat style to rent depending on how adventurous your guests feel and whats their level of familiarity with sailing.The J/22 provided by Chicago Sailing had their below deck emptied out, a choice that makes sense for simplicity and maintenance considerations, in addition to the fact that the law forbids all discharges into Lake Michigan. People who are not familiar with sailing or with this law may find it surprising or uncomfortable to be unable to use the head (i.e., toilet) on the boat; they should organize their trip ahead to avoid surprises.In conclusion, I recommend Chicago Sailing and Ill be using them again. I dont know any way in which they could improve their service... the only way to improve my level of satisfaction would be a decrease in their hourly rates...

The staff at Chicago Sailing are very friendly and helpful. We rented a J22 from them, which is a joy of a boat to take out on the lake.Unfortunately, there was miscommunication during the checkout process prior to leaving the marina and we were unaware of two of their rules: one being the boundary and the other being the dual power requirement into the marina (i.e. entering/exiting under sail).I was always taught to raise and lower sails outside the channel for safety and to prevent accidental jibes. They claim it is necessary as a backup in case the motor fails (an overly cautious fail-safe in my opinion). The other consideration was the small boundary in which you could sail. I found them to be an inconvenience at best and would say they are unreasonable if you bring back your boay within the alloted time-frame.Rules are rules, however, and I would have had no problem following them if they were made more clear. The primary reason our experience turned sour, was the owners poor attitude and lack of customer service consideration. Owner, I imagine youre reading this: so sorry, but you were a jerk.Overall, this is a great opportunity if you enjoy sailing. Just beware of making a mistake and getting chased down to be berated, not a pleasant experience.Technically, I found the motors to be very reliable, though they didnt have a reverse gear. You get a safety box with a flare and first aid kit but NO RADIO, I understand theyre expensive but that could be a liability issue considering most phones arent waterproof. The built-in reef on the sail with a bowline knot is also a bit annoying and messes with the sail shape.Those are my only criticisms and hopefully o theres get treated more nicely. Other than that, I believe this is a fine establishment which offers easy access onto Lake Michigan. I recommend it, but heed my warning, the rules are stringent.

Loved the sailing experience.