Chicago Sailing

As someone who primarily sails in New York but recently came home to Chicago for a girls trip — this past weekend we wanted two hours on the water as we sipped a cold drink and chatted amongst ourselves.
I will say that I was 1) expecting a slightly nice and better appointed boat for the price. And 2) Rick, one of the captains was a really strange dude. Did he want to tell us about being a poet? About his girlfriend? Yes. Did he decide not to turn into the wind to put the sails up but ask us inexperienced sailors to take the wheel (at the tail end of the air and water show when there were tons of boats out) as he frantically ran about? Yes. Did he basically do hairpin turns with the motor on to try to steer into the wakes of other boats therefore giving a good case of whiplash? Yes. It I guess was fun at times but it didn’t feel as nice or luxe as I would want for the price.
At one point I would actually note that it didn’t feel safe. Not because Rick was a bad sailor but because he just wasn’t communicating and was acting frantic. Look, if you want everyone on the boat to help, let’s establish that before we take off from the dock. Let’s talk about what will happen, what is expected and if we actually want to get involved. The chaos while moving fast in the harbor was just a little out of left field and uncomfortable.
I would think about doing this again but I would inquire about the boat selection and I would ask for a captain that is not Rick.

We could see the boats happily tooting around from our window and decided we ought to try it, so we took a series of lessons from Chicago Sailing. The operation, and especially our instructor Chip, were excellent. Chip was great about maintaining enough control so that we felt safe early on, but quickly giving us more responsibility as we learned. And he, like us, preferred to spend as much of our lessons as possible out on the water.
I just wish we had more time in our days to get out on the water. We’ve already put the start of this year’s sailing season in our calendar.

My in-​laws were in town over the weekend and thought it’d be fun to treat then and my parents to a sail boat ride down lake michigan. The price is kind of steep but I imagine its the going rate for this type of activity.
We rented the T-​30 sailboat (max cap. 6) for two hours. Even though the water was a little rocky, we all loved the trip. If a sailboat captain is needed, I highly recommend you ask for Charles. He was very professional and knew a lot of information about the Chicago architechture. It’d give it 5-​stars but think its a little on the expensive side.

I had a great time learning to sail through Chicago sailing. I knew nothing about sailing other than that it looks like a lot of fun, but my friend and I signed up for their Sailing 101 course, which consisted of 4 consecutive days of 4 hours on the water.
The instructor (who reminded me of Fred Willard (the pre-​movie theater scandal Fred Willard, that is) took us and another 2 beginners out on a 22 foot long sailboat and we all took turns doing everything required to sail, from learning the required knots, steering in and out of the harbor, taking in and putting down the sails (I’m using all the wrong terminology here, forgive me since it’s been a while), and everything else you’d need to know for a day out in the water.
At the end of the instruction he talked with each person individually about whether we were at a point where we could take a boat out on our own, or if we should sail with someone more experienced for a while longer. With the instructor’s sign-​off, taking this class certifies you to rent a boat from Chicago Sailing.
For me, I found out that I enjoy sitting on a sailboat helmed by someone else more than being in charge (it allows for more quality drinking time!), but I would definitely recommend this program to anyone interested in learning how to sail.

I was with a group of 6 women and we were looking forward to a fun day out on the water. We advised the company when we made a reservation that we were a group of young women in our 20’s and were looking to have some fun, have some drinks and just have a good time.
This message was not communicated to our captain. He insisted on giving us each sailing lessons (which we did not want), would not take us to the Playpen (the area where a lot of boats dock and people are hanging out and socializing), took us to Bird Island after we specifically said we did not want to go there and was overly involved in our conversations throughout the entire time on board.
We were just looking for someone to sail us around and allow us to enjoy eachother’s company, not to be our father and story teller for the day.
Overall it was great being out on the water, but this was definitely not the experience we were looking for. If you are a group of girls going for a bachelorette party, etc., I would suggest looking elsewhere.

Very friendly, helpful staff. Reasonable prices.

I took the 2 hour sailing lesson with them today — Sunday afternoon in June! The weather was great.
What was even better was — the class itself. Our instructor Dave (from Ireland) was super proficient. He knew how to teach basics to two novices and make it fun!
I truly felt like the class exceeded my expectations, from both a fun and knowledge perspective!
Would totally recommend it!

Thanks to Chicago Sailing I’ve had the summer of my life. It started with Sailing 101 and grew from there. I am now U.S. certified and just finished training for operating the larger boats. The instructors and staff at Chicago Sailing are wonderful. If you have ever thought about doing this — don’t wait. This is the place to learn and begin your life as a sailor!!!

I am very disappointed with their customer service. I got a living social deal, but when I went to schedule it in July, there were no weekends and very few open dates before the expiration in September. I was advised to just schedule a spot and reschedule if needed. Unfortunately, due to my work schedule (I am a surgeon), I could not reasonably make a 5pm time, and they notified me that this would cost $ 50 to reschedule, and would essentially forfeit my voucher. This is a total scam, because they sell more tickets than their schedule can accommodate. If they could provide more weekends, it would be more reasonable.

YAY!!! I have been wanting to take sailing classes for a while, and a living social deal helped me get a glimpse of sailing.
I bought the deal early in the season and didn’t call to make a reservation until early August… I figured this would cause an issue as I was concerned that the classes would all be booked. A really friendly guy answered the phone when I called to make a reservation, and he called me back with some options of classes (and also let me know that they were going to extend the date on the living social deal). In any case, I picked a day and the rest is history!
I loved my class! I wasn’t sure what to expect and I admit, I was a bit nervous. It turns out that the classes are very relaxing and everyone that works there is extremely friendly. There seem to be about 4 people per boat with an instructor. Our instructor was Alejandra (spell?) and she was super helpful. Involved in races since she was like 10? Awesome! She was new, but she was talented and really friendly and good with the group.
I took the 3-​hour class and I want to take the 5-​day class next season (if I take it now, I’m sure I will forget everything…). In any case, the class is great. Each boat only has a few folks, so everyone gets a chance to try things out if the want. I was a bit disappointed that someone on our boat was ill… not that he was sick per se, but that he didn’t want to go back in… so we spent a bit of time checking on him (note…if you get seasick or aren’t sure, take some Dramamine… it happens to the best of us, but try to avoid this for the rest of us…).
I truly enjoyed this and can’t wait to go back. I also want to sincerely apologize to my instructor as I had no money to tip… were we supposed to tip? It’s so hard to determine… again, I’m sorry, you were super!!!

Horrible customer service!
We made reservations to sail one day in June. The day of, there was a small craft advisory, and overall hazardous marine conditions. A warning was issued. The temperature was approx 50 deg and winds were up to 20mph. Despite hazardous conditions, Chicago sailing is charging us a 50 $ rebooking fee. It is hard to believe that a sailing company would not let us cancel our reservation when hazardous conditions exist.
We have been coming to to Chicago Sailing for approximately 5 years so I guess customer loyalty is of no concern to them.
WOULD NOT RECOMMEND. Do not book ahead of time unless you are willing to put your life at risk, as CS seems to be.

If you want to sail in Chicago and do it the fun way — economically, then get over here. Ask for Heather.

The best 2 days in a boat owners life is the day he buys and the day he sells his boat!
If I owned a boat I would feel hugely responsible to get there every weekend which is not reasonable. with renting you all of the pleasure and none of the woah.
I have been sailing for many years and these guys do it right. clean boats, new boats, great communication and very friendly service.
Last year I rented during the air & water show. You will not have more fun than that on a boat… almost!
Experience or no experience this is the place. I have not found a place like this is any town in Florida of California.

Back in June 2008, I got a super awesome birthday present from my boyfriend. What was it you ask? Sailing Lessons (Basic Sailing 101) at Chicago Sailing.
Unfortunately for me, I got really really sick before my first lesson, so I had to miss it, but luckily I was able to quickly catch up. My instructor was named Andy and he was pretty nice. Answered whatever questions we had and showed us the basics of sailing, but also making sure we were having fun. We all got to take turns doing everything and had a pretty good idea of what we were doing by the end of the week.
The other people at the dock were friendly too, which was a nice bonus. All in all, a very cool experience and I’d definitely take a class from them again.

B Dock rentals rule! (located in belmont harbor, off recreation drive, past harbormaster’s bldg)
My two friends and I showed up here after a grueling morning looking for a place to rent small sailboats. The wonderfully nice people at Belmont Harbor helped us get out on the water in no time (granted I do have considerable experience sailing small boats, and there was a boat check/​rig check). I don’t think they would rent to you unless you had some experience handling boats, motors, and maneuvering in the harbor/​harbor mouth.
The rental was $ 140 for two hours (there is a two-​hour minimum) on a J-​22. They also rented bigger racing catamarans (but I didn’t catch the price for those). The J-​22 was in great shape (we took out «Peter» but I wouldn’t have minded «Catch 22», just for the sake of its name) and was easy to rig up. You could probably fit up to 5 people on a J-​22, and they have a little cabin for stowing a cooler or some beach bags.
Mike was great and helpful at getting everything ready to go for us, and we were out on the lake in no time! (check out his purple keds! totally sweet. my crew was rocking vans, but both are great for boating i think).
5 stars for service! 5 stars for boats! 5 stars for timing and being the only people in chicago (practically) to rent boats from anymore!
Of course, it was a bit pricey, but hey, it’s chicago, not like some sunfish-​renting, boats-​on-​the-​sand-​place in a small beach town.

After living in Chicago for over 5 years and having never been on a boat (outside of architecture tours), I decided to finally do something about it! Over July 4^th weekend, some friends from out of town and I chartered a sail boat through Chicago Sailing. It was such a blast!
Booking the ship was so easy and the staff and crew were so accommodating. Our captain (Matt) was great — a very experienced sailor who taught us a bit about sailing as well (even let us help a bit). We were able to bring food and drinks and essentially just chilled out for 3 hours on Lake Michigan.
My only complaint would be the capacity of the boats (you can either get one that holds a max of 6 or 30 — nothing in between). They do have a 72 hour cancellation policy, which in Chicago (especially given our recent bi-​polar weather conditions), can be tricky, however, I do understand why they have it in place. Pricing is way less than I would have thought (it was about $ 90 a person for 3 hours during a holiday weekend — prices are less during the week). Will definitely look to do this again when I need another boat fix.

I loved the sailing lessons I took from Chicago Sailing. I was surprised at how much I learned in just one lesson. Our instructor was patient and explained everything beautifully — he also made sure we were having fun! I found the staff very friendly and I look forward to trying one of their club sail events. I’m not sure I’ll ever have the means to own my own boat in Chicago, but at least now I can rent them! I’m thrilled that I found Chicago Sailing — they make it so easy for anyone to enjoy sailing. I can’t wait to take more classes next summer.

My first summer in Chicago I lived in a small studio 36 floors up in the The New York condominium with an amazing view of the the full lake and downtown skyline (courtesy of a Craigslist post one week before I needed to move). Seeing the sailboats embark every weekend morning by the hundreds expanding across the lake sails taut with wind piqued my interest.
The following summer I decided to take the plunge after researching it online. Chicago Sailing was down-​to-​earth but on top of their stuff administratively; a good combination in my opinion. I signed up online and received a PDF file e-​mailed to me with the details.
I’m a sailing rookie other than one attempt in Ohio previously and I don’t have any gear, just a windbreaker and jeans which is pretty much the ‘uniform’ of most here minus a couple instructors who overdo it in a full suit that looks fit to dive in. I’d suggest bringing a waterproof case for your cell phone, etc. or at least a Ziplock bag (even the cabin gets wet in parts).
My instructor had a ‘normal’ engineering job during the week. My crew mates were varied. My popped collar Polo image of sailing shattered. Although I’m sure that variety still exists.
I would not say its easy but it is very doable with your instructor and crew’s help. I would especially read the book more thoroughly and watch the online videos repeatedly if I would do it again (and I plan to next summer get a certification).
The satisfaction with achieving something difficult combined with the amazing experience (and view of Chicago from the water) definitely made this one of my favorite experiences.
Jibe ho!

One of the beautiful attractions of Chicago for me – and at least one reason I moved here — rests just East of its high rise buildings. And a terrific way to experience this jewel of a lake is by boating. Now I have always enjoyed motor boating, but something about harnessing the wind to power boat travel romanced me, enough to try sailing.
The Chicago Sailing Club did not disappoint; I spent the weekend mornings of a summer learning to sail with one of its instructors. She was a terrific sailor and a friendly teacher. I would recommend her specifically, but she has since moved. However, I suspect the camaraderie felt there is institutional with the Club.
I credit my education here to now ably spinning wild tales of sailing a catamaran along Amalfi’s high seas in Italy.