ChicaGo By Boat

4.7 (13 reviews)

Boat Charters, Boat Tours, Boating

Closed • 9:00 am - 10:00 pm

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ChicaGo By Boat - Boat Charters Near Me - Chicago, Illinois

ChicaGo By Boat - We enjoyed our time and will definitely be back again! - Boat Charters Near Me - Chicago, Illinois

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ChicaGo By Boat - Skyline - Boat Charters Near Me - Chicago, Illinois

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Isabella C.

3 years ago

So fun! Highly recommend this company. They take the time to call you beforehand to make sure all your questions are answered. My family and I got captain Larry and he was so kind and told us fun facts about buildings that we passed by. I will for sure be doing another boat tour with them!! read more

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Anna M.

5 years ago

Excellent time on Lake Michigan. We had to reschedule our first appointment due to bad weather and were so happy we made it back to Chicago just for this trip. We got lucky to have good wind and had a true sailing experience. Captain Conway knew what he was doing and we always felt safe and in good hands. We would certainly recommend this charter to anyone looking for a sailing trip while in Chicago. We will be back! read more

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Linda D.

8 years ago

Trust Capt, Conway and ChicaGo By Boat for all of your sailing needs! Sailing is kind of my thing. There's nothing like relaxing out on the water with friends as we enjoy the inspiring views of Chicago. I'm not talking about a booze cruise. Sure, you can find those all over town. My first summer in Chicago I met friends with sailboats and was converted from the idea of a booze cruise to the perfect floating patios with close friends and instead of crowds. Ahoy! Enter ChicaGo By Boat. I first went sailing on a semi-private charter with a visiting friend: It's a fine way to mingle and take in Chicago from Lake Michigan. It's also an excellent intro to sailing. I was invited me to try a private charter. Fortunately I knew of some friends who would join me. The owner Captain Conway always make me and my guests feel like VIP's from booking to boarding to disembarking. They're very professional, responsive and flexible. Whenever there's a weather concern they've called ahead and communicated to give us the latest details before heading to Burnham Harbor. Captain Conway is very welcoming so it's more like entertaining and sailing with friend, than a generic charter or a set tour around the pier. He works with all levels of comfort with water, sailing and athleticism. Conway also has some entertaining stories of people places things that have come up under sail. Sporty, lively and heeling? Check. Relaxing and enjoying the skyline views? Absolutely! BYO summer menu with paired beverages and tastings? They've become a stellar go-to summer choice. Summer birthdays aboard Nightswimming? Certainly a luxury sailing vessel and first class event! They have several ways to let party hosts relax and lighten the load. When we have a group of 6 we can get an extra crew member to help. There's bottled water for us as well as a refrigerator, ice and plastic drink ware. Have a VIP, corporate client or the need to sail from DuSable Harbor or Belmont? Captain Conway and his team have always been able to help! With this relaxed and professional vibe everyone is instantly at ease and guests ask when we can sail next. Sometimes my guests and I enjoy a cocktail skyline sail, other times it's water, Pellegrino and an athletic day finding the best wind. Plus, the wind and the waves conjure up an ideal mix so it's like a built in spa day! And, it's wonderful to see more social media support for sailing. Thanks for everything Captain Conway! Sailing in these conditions again? YES, please! read more

ChicaGo By Boat - Another perfectly relaxing skyline sail w/ChicaGo by Boat! We love sailing with Capt. Conway w/friends dates & family. Thanks & fair winds! - Boat Charters Near Me - Chicago, Illinois

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Amanda K.

4 years ago

AMAZING!! Captain Conway is simply the best! He truly went our of his way to ensure we had the best sailing experience. He went above and beyond what any of us expected, and absolutely made our day so special! He is friendly, professional and so knowledgeable. We felt confident every step of the way and had the BEST time! The boat itself, Nightswimming, is beautiful and meticulously cared for. The views of the city can't be beat and the memories will last a lifetime. 100% BOOK THIS CHARTER read more

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Chris J.

204

7 years ago

We met Captain Conway last year and we've sailed with him multiple times, usually in the morning when the waters and nice and calm. He's such a nice guy, making our sailing experience enjoyable every time! We officially call Captain Conway our "Chicago boat friend" and will book many more adventures with him. read more

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Conway B.

Chris,…

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Andrea K.

3 years ago

We have chartered with captain Conway numerous time I have been sailing and we have done the air and water show on his sail boat 2 years in a row. Super fun then planes flew right over us. The captain is very friendly and professional. This is a must do. September is coming and that is my favorite time to sail read more

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Cath E.

8 years ago

Such an amazing experience!!! My boyfriend came across Captain Conway through a google search of charter boats in the Chicago area. He was looking for a romantic way to propose and nothing could have topped this!! Captain Conway was nothing but accommodating for the whole experience, serving us wine and champaign after my boyfriend proposed and captured some amazing pictures. The entire night was so private, romantic and amazing. 100% would recommend this experience for everyone looking for a private charter experience. Very affordable compared to other charter services and the experience was customized just for us. Thank you Captain Conway!! read more

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Elise D.

8 years ago

I recently moved to Chicago and was looking for something to do away from the typical crowded tours and activities. I came across a private charter and Captain Conway and am excited to say I am a repeat customer! I couldn't ask for a better experience to bring visiting friends and family to show off the Chicago skyline and Lake Michigan. There was a fridge for byob drinks, ample seating and Bluetooth music. I cannot believe how impressed I was with the whole experience!! When planning your next activity in Chicago, sailing with Captain Conway is A MUST!! read more

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Ian Q.

7 years ago

ChicaGo By Boat is the best way to experience Lake Michigan and Chicago's beautiful lakefront. Captain Conway owns the company and sailboat with his partner and wife. Cap is a consummate professional who has decades of sailing experience from Chicago to Boston and Seattle to the Caribbean. The boat is stunning. Captain Conway has updated it with top-notch technology without losing its beautiful character. You are going to have a good - and importantly, safe - time with ChicaGo By Boat. Captain Conway provides thorough information with everything you need to know about setting sail with him. Remember, this ain't Disney World!! This is a real sailboat on a real lake!! So read the info ahead of time so you know what to bring / not to bring, etc. Do yourself the favor of having the best time of your entire summer with Captain Conway on Nightswimming!! read more

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Conway B.

I wish I could review Ian Q. as a Five Star guest! This was not our…

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James J.

7 years ago

Super fun time sailing on the lake. Beautiful boat and great captain. Highly recommended for family, friends, and team building for work. Thanks! read more

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Conway B.

James,…

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Ashley K.

6 years ago

Sailing with Captain Conway is a dream. I've taken two charters with him and coworkers...he runs a clean and perfectly-timed sail, his boat is meticulously kept up, and he is extremely accommodating. I could not give higher praise of his professionalism, kindness, and how safe he made us feel sailing during COVID. I plan on many more charters and highly recommend!! read more

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Carrie N.

8 years ago

An amazing Chicago experience! Reasonably priced too. We booked a private Saturday fireworks sail for date night and drove in from the suburbs. Couldn't have asked for a more perfect time! The city skyline view, Captain Conway's knowledge of the lake and history of the city on point! Perfect summer weather. Thank you ChicaGo By Boat!!! It was a night we will remember forever! read more

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Shmandy S.

7 years ago

Used this service over the summer and honestly felt bad that something which was supposed to be a gift and fun ended up ruining the day. Interactions were super uncomfortable to where it was impossible to enjoy it. The captain was cold, moody, and left us feeling personally and unfairly judged almost immediately to the point I'd have rather we turned around early and just been able to leave instead of finishing our time on-board. Look elsewhere. read more

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Conway B.

Shmandy,…

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More info about ChicaGo By Boat

1559 South Lake Shore Dr
Q Dock
Chicago, IL 60605
Near Southside
Directions
(833) 312-2628
Call Now
Visit Website
https://www.chicagobyboat.com

Payment methods

Does ChicaGo By Boat take Bitcoin?

No, ChicaGo By Boat does not take Bitcoin.

Does ChicaGo By Boat take credit cards?

Yes, ChicaGo By Boat takes credit cards.

Indoor Amenities

Does ChicaGo By Boat allow dogs?

No, ChicaGo By Boat does not allow dogs.

Outdoor Amenities

Does ChicaGo By Boat have bike parking?

Yes, ChicaGo By Boat has bike parking.

Does ChicaGo By Boat have parking?

Yes, ChicaGo By Boat has parking options. Garage Parking, Private Lot Parking, Street Parking

Other Amenities

Is ChicaGo By Boat wheelchair accessible?

No, ChicaGo By Boat is not wheelchair accessible.

Does ChicaGo By Boat have free WiFi?

No, ChicaGo By Boat does not have free WiFi.

From the Business

Specialties

2020 Sailing Season Update: We feel it's time that we all get outside and enjoy ourselves and the 'Chicago' Summer. So, ChicaGo By Boat is excited to be able to introduce private sailboat charters in Chicago's North Shore. The S/V Nightswimming now departs multiple times daily from Waukegan Harbor and Marina. We invite private groups of up to six guests to book your boat charter so that we can host you on your own unique sailing experience. ChicaGo By Boat offers Chicago's premier affordable luxury boat charters. We invite private groups of up to six passengers aboard the S/V Nightswimming for two to three hours based on our guests' needs. While on board you can watch the sun set behind Chicago's skyline or watch a full moon rise out of Lake Michigan. You can also experience the Wednesday and Saturday Navy Pier Fireworks from the front row. Want to host your corporate outing? We can do it. Want to propose to your partner on a sailboat? Perfect! The annual Air and Water Show as well as Museum Campus, Northerly Island, and Soldier Field events are some other opportunities to experience the water. Or, maybe just sail with us because it's your Sunday Funday or you're on a staycation!

History

Established in 2018.

2018 was our inaugral sailing season; our proof of concept; the solo album. When we started ChicaGo By Boat we began with the motto that, "Whether it's your first time, only time or just the next time; we want your sailing experience with us to be the BEST time you have this Summer."

Meet the Business Owner: Captain C.

The owner and master is a professional mariner with over 10 years experience as a licensed USCG Master Captain. Their career has taken them from the Gulf of Mexico to Boston Harbor to the Willamette River to the San Juan Islands, and Lake Michigan ever since 2010. They have commanded vessels from 8' to 148' and everything in between.

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Review Highlights - ChicaGo By Boat

“I couldn't ask for a better experience to bring visiting friends and family to show off the Chicago skyline and Lake Michigan.”

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Wendella Tours & Cruises

4.4

(1.6k reviews)

First time on the architecture boat tour on the recommendation of a bunch of friends who had…read morealready taken the tour in the past. Personally, I was pleasantly surprised. The words "architecture" and "boat tour" don't immediately spell a fun time in my mind. But this tour is 1) a pleasant way to see the center of Chicago from the water, 2) actually interestingly informational, as the tour guides are extremely on top of their game, 3) much more dense that you expect (these guys are talking non-stop), and 4) surprisingly good views, especially when you get all the way out into the edge of the harbor! Finding the place was a bit roundabout, but once we got there, staff were super friendly, and it was easy to get on the boat and off to our next stop afterwards. Parking suggestions on the site are solid too. I'm not sure whether I'd do it again, but I'd definitely recommend it as a must-do stop on any visit!

90 minute Architecture tour…read more It was a cloudy, windy, and cold day in June. Even with the clouds rolling in & out and blocking a lot of the views it was still interesting and our awesome guide, Bobby, was knowledgeable, funny, and kept it interesting and flowing for adults and kids. The tour starts on the river heading towards Lake Michigan. The ride into the lock was a little lengthy as we had to wait for them to fill it with boats first. Once we made it onto Lake Michigan it was very chilly, but I'd rather be freezing than sweating like crazy on a hot humid day. We were on a smaller boat which was nice. - upper deck: Seats long the outside and chairs in the middle. Only wish they had cushions. - lower deck: had some small seating outside and standing bar tables - lower deck: indoor restrooms and bar area - snacks, drinks available for purchase If rain is in the forecast bring paper towels to clean off your seats. I also saw some people with Wendella rain ponchos, but not sure where to get them? Really fun and beautiful way to see the city! Highly recommend!

Chicago Architecture Center

4.8

(821 reviews)

Definitely one of the must do while visiting Chicago!…read more Great boat tour with excellent docents. I ended up with a much great understanding of the Chicago buildings I was walking around or through.

My friends and I boarded the Chicago Architecture Center's River Cruise aboard the First Lady on…read moreThursday, July 23rd. We'd pre-purchased our tickets directly with the operator and paid for priority boarding. It took us a few more minutes to arrive than we'd anticipated, but it was easy to find the location the cruise departed from. Luckily, even though they'd already begun boarding the general admission folks, we were allowed to skip the line and our priority boarding was honored. Our guide's name was Russell and he's a volunteer docent. He was wonderful and his explanations were very interesting. It was a great way to get to know the stories behind the buildings and to see the city from a different angle. Highly recommend!

Shoreline Sightseeing

4.7

(1.9k reviews)

Eric was a very good speaker and staff war very nice, the entire thing was very informative thank…read moreyou guys so much!

This tour was on the top 10 list of our things to do in Chicago. I researched all the boat…read morecompanies that offered the Chicago architecture boat cruises and Shoreline Sightseeing came out hands down #1 for us in tour length, type of cruises, accessibility and in price for what you got. Best deal. Our tour guide was happy, energetic, and very knowledgeable about Chicago because he was born and raised there. We chose the 75 minute, 4pm Chicago River tour and it covered a lot! We never lost interest and learned about Chicago's history. It is well worth it! Our Architecture River Tour boat departed from the dock at Navy Pier. We learned that their boats are the most accessible at this location. Their boats can accommodate wheelchairs up to 30-inches wide. Your wheelchair must be able to navigate a ramp with a 2-inch step at one end. I needed one that was kind to my knees. Best to call them for more details. They were very helpful whenever we called them. Their boats are both double-decker and single-level boats, and there is generally no protection from the sun, rain, or wind. There is a small bar on the main level. Restrooms are located on the lower deck, which is accessible only via stairs from the upper deck. Enjoy! It's amazing!

Chicago Fireboat Tours

4.9

(66 reviews)

A beautiful day on the Lake Michigan. Had a blast on Veteran-owned FIREBOAT-TOURS today! Such a fun…read moreafternoon soaking up Chicago's history and architecture from the water. The itself was comfy and solid, and it's pretty cool to think this fireboat served the city's fire department from 1937 to 1981. Lucky us, we caught a perfect day light winds and clear blue skies. Thank you to Cliff, our tour guide, who had serious knowledge of Chicago history and a fun vibe was fabulous. The bartender, magic manning, was a total character, bringing good energy and making sure everyone had a good time. In fact, the whole crew was super welcoming and made the experience even better. Next time we are going to try the sunset cruise and do this all over again.

This fireboat tour was spectacular! My friend and I both had a wonderful time and can't recommend…read moreit highly enough. The length of 2 hours was perfect so we didn't feel rushed. We motored around near Navy Pier and on the river. While I'm generally not into architecture, the buildings were beautiful and interesting to learn about. I expected that the tour would include a recording of the information about all the sights, but the person narrating the tour did so live. He came up and chatted with all the passengers a couple of times. We felt very well cared-for. Word to the wise though, it can get a bit chilly so wear layers if possible. Highest recommendation!

Chicago Architecture Center

4.6

(563 reviews)

•$

A neat small place to learn about Chicago architecture and it's development, with short…read more timelines on the walls and miniature model of the city and another ofWrigley Field. I bought a perfect, sturdy canvas bag labeled Chicago Architecture Center.

Entry to the museum is only five dollars if you show them your ticket from the First Lady boat…read moretour. The ground floor has a short eight minute clip with information about the city. There is also a great display of the city as well as a Wrigley ballpark exhibit. Unfortunately, the upstairs is currently being renovated, so there was not a lot to see this trip. They have a great gift shop.

Chicago River Boat Architecture Tours

4.7

(290 reviews)

Our guide Victor was impressively knowledgeable and made this so enjoyable! We went at sunset and…read moreit was beautiful.

Such a great city for architecture, the very oldest building sitting next to the newest…read moreskyscrapers. I loved this tour...even though it rained and we had to spend part of the tour inside to stay dry without much of a view, it was still a great tour for the cost. We were warned to make a reservation cause the tours do fill up, and this was a holiday weekend. Do not leave Chicago without doing this!

Shoreline Sightseeing

4.5

(154 reviews)

Sam S. Was great today!!! Very knowledgeable and good humor as well. A+++++++ would love to do…read morethis tour again soon.

Quick take: Must do in Chicago…read more Definitely go on a river boat tour if you are visiting Downtown Chicago. The tour guide was awesome. The weather was so nice. Not too hot and not too cold. Very interesting history and stories about all the businesses and buildings along the river.

Seadog Cruises

4.3

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I was terrified of boats, so I was very scared to try the Sea Dog Speed Boat. Instantly, I was…read moregreeted with a friendly smile from Avery! She was so sweet and gave us a ton of facts! When she was talking, she was smiling and dancing to the music! 10/10, I will have to go again!!!

Great team and an amazing boat ride cannot complain one bit. The architecture tour is definitely…read moreworth the money.

Tours & Boats

4.7

(71 reviews)

David did a great job leading this tour! I left with a newfound love of architecture and the city…read morethat surrounds me. Highly recommend the architecture tou, ( and the cocktails !! )

Bought tickets from Groupon and it was not exactly a smooth transition unfortunately. Our family…read morewas visiting from CA and we purchased 5 tickets for the 2pm tour. When we arrived, we were told 1 of the 5 was for a later tour. Well that doesn't work. The ticket guy was trying to work out the error and another employee stepped in and was rude. He was stern and said, "it's sold out either part of your party goes and the other party can catch the next tour or you go on a wait list. We had tickets for 4 out of 5 people. I understand sellouts but we were there at 130pm and we were confused about what had happened. Well, the ticket person was nice and let my nephew go with the group. I thought the second person was rude. I'm glad the ticket person understood what happened and accommodated us. The tour was great, our guide was awesome. His name escapes me now and I am good about remembering! He was so knowledgeable! I would say they should consider the age because we had little kids who were not managed well by their parents and also a couple next to us talked the entire time. Our guide was polite but did say something to them but they kept talking. I would say the boat rules should be posted or something for folks to be quiet! Highly recommend it but if you do Groupon, it refers you to tours & boats website to book so triple check your tickets.

CE Boating

5.0

(1 review)

I always have the best experience with CE boating I've used them for my annual boat experience for…read more3 years in a row they always come through! The boats are very nice and fit a decent amount of people ! 10/10!

From the owner: We are closed for the 2025 Season and will return for the 2026 Season. We will welcome you back…read moresoon to book your private boat rental with CE Boating in Chicago. Cruise Lake Michigan, pop bottles, relax, and celebrate. Limited spots.

Waterfall Glen Forest Preserve

4.5

(162 reviews)

Well maintained. Not too crowded…read more Challenging enough on a bike for me. Beautiful and well maintained trails that are well marked. Love it. If you're out of shape this place can whip you back into shape if you let it.

Waterfall Glen is a beautiful display of nature. Trails offer a robust adventure. Two parking lots,…read moreone off of Cass Avenue and the other off of Lemont Road.

East Bank Club

4.0

(354 reviews)

Gorgeous health club!! My friend belongs here and I joined her for dinner at the restaurant/grill…read more The food was tasty and excellent service. I was given a 90 minute pass for dinner and they seem strict on the time. My friend also gave me a tour. It's an impressive space!! About 450,000 square feet, spanning across 2 full city blocks and 5 levels. They have everything you can think of: pools (4 pools!), saunas, restaurants, tennis, golf, basketball, boxing, group glasses, weights, machines, pickleball, spa, hair and nail salon, indoor running track, co-working space, and so much more. Beautiful artwork, pristine locker rooms and restrooms. Wow! High ceilings and so much space overall. Nothing felt crowded. Beautiful design and layout. I was in awe and very impressed.

(Kari's Rating 7.5/10)…read more TLDR -Up-to-Date equipment -Work from home spaces -Convenient Healthy Market Came with a friend to hang out on a Wednesday around 5:30pm to see what East Bank Club is all about. After seeing all the crazy amenities which were super cool with a ton of variety, I think the thing that surprised me the most is how up-to-date all of the equipment was and the variety of activities they had for people to enjoy. If you're looking for an all encompassing workout/work space, this is it! They have everything from full-size tennis courts, to a golf simulator-like set up,except you get to hit into an inflatable pillow! They also had plenty of Pickleball courts, and they offer so many different workout group classes.both a wet and dry, sauna, and tons of treadmills and free weights. I was also really impressed that they also had a physical training area. So think something that was my personal favorite and the best thing for Chicago Summers is a beautiful rooftop pool and lounge area. Not only did they have two outdoor pools (one for adults and one for kids) but they also have an indoor pool as well for winter as well as an indoor hot tub! They also had a common area workspace where people can come to take meetings and do their work from home gigs. You could practically move in here haha! As of right now, it is a $750 new membership fee as well as $295 a month, which is a pretty hefty chunk of change if you ask me considering most of the high rises around, have some kind of rooftop pool and workout area. It is cheaper if you join with a domestic partner or if you're between the ages of 16 and 29-see pic for current pricing. They also sometimes host social events which is super fun to meet everyone else in the club, but at the same time I think it is more of an investment in your future and your future health if you can afford it! I will not be joining at the moment, but hey-that could change anytime if I decide I should be on a health kick.

Meadowlark Golf Course

3.8

(24 reviews)

Course was in good shape and staff are friendly. It's unremarkable to play but generally wide open…read moreand easy to walk. Pace was slow. Plenty of carts available. There's a grill setup on hole 4 with all the usuals you'd expect and the porta-potty is accessible from a couple different holes. The clubhouse bathrooms are gross. Price is good.

9-hole course. The staff is very accommodating and nice. No external alcohol allowed, but they do…read moresell snacks and drinks on site. Golf carts available for reservation. The brush around the course is pretty thick because it's located in a forest preserve, making your chances of losing balls higher.

UIC Student Recreation Facility

4.0

(28 reviews)

Great facility open year around BUT CLOSED FOR SCHOOL…read moreHOLIDAYS! Spa and sauna are super nice. The rec app says there is a Pilates reformer but no classes to sign up. Testing to find out if true.

**UIC Swim Classes: A Budget-Friendly Option for Kids**…read more We enrolled in UIC Swim Classes for our 1.5-year-old and found it to be a solid, budget-friendly option. At $22 per session, the classes offer structured swim lessons at a more affordable rate compared to other local options. There is a chill vibe that works great for a 1st learner, but the level of rigor is lower than Goldfish so we switched there once we got off their wait list. Classes are sold in 5 week packages, and reschedules are not typically allowed. The class structure follows a set sequence of exercises. Instructors are friendly, but engagement is inconsistent. While they guide kids through various activities, the level of encouragement and feedback varies, with some instructors mentally checking out after providing initial directions. The UIC facility itself is quite nice - The water is comfortably warm and there are changing areas. Parking is available but paid for a few dollars. Note that your access is restricted to within 15 minutes of class time, so don't go too early. Though there are fewer opportunities for underwater practice and confidence-building dips, the parent/tot classes are primary about getting your kid comfortable in water. Overall, UIC Swim Classes deliver decent value for the price, though parents seeking a more intensive training that will get kids swimming faster may want to explore Goldfish.

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Scott C.

111

8 years ago

I've gone out sailing with Captain Conway on a few occasions with friends and family and just scheduled an outing with my coworkers from out of town. Mainly to show them why Chicago summers are the best. Conway showed us the best views of the museum campus, navy pier, and a skyline shot you just can't get anywhere else in Chicago (I recommend sitting up near the bow). He's shared stories of sailing on every coast of the country and has been sailing on Lake Michigan for years so I quickly figured out I didn't need to come with a plan. The boat was spotless, Conway and his crew were awesome, he had a fridge to keep my beer cold (Something I hold near and dear to my heart), Bluetooth speakers, sneaky quiet motoring in and out of the harbor so my friends can hear my bad jokes (I only have so many opportunities), and overall, Conway provides a safe stress-free sail. Pro tip: Whether you're trying to convince someone to move to Chicago or just remind yourself why you live here in the first place, Conway is the Captain to sail with! read more

Vince B.

8 years ago

When booking charters two things are non-negotiable: 1. A Savvy Captain 2. A Flawless Boat I have been renting summer charters in Chicago since 2004 and have seen more than a few duds. We stumbled upon Captain Conway several years ago and have asked for him by name from that point forward. He is a skilled sailor, knowledgeable Chicagoan, and genuinely laughs at bad jokes. He has a knack for quickly assimilating into any group dynamic and is one of the best color guys in the business. As far as the boat itself, Captain Conway is a bit of a perfectionist. Each boat is impeccably cared for, cleaned, and outfitted with premium fixtures and amenities throughout. I am always impressed by his attention to detail each and every time I step aboard one of the Captain's boats. In sum, the entire ChicaGo By Boat team cares and it thoughtfully shows throughout the entire process from booking to final approach. This is the place, and now you can tell your friends, you've got a guy. read more

Arrington C.

5 years ago

This was our second year sailing with Captain Conway and we could not speak more highly of the experience! Captain Conway is delightful and punctual and fun and puts safety first. His boat is beautiful and spacious and fully equipped with cups/utensils/plates, anything you may need! Burnham Harbor was incredibly easy to get in & out of (we parked in the Shedd's lot- $30 for 4+ hours). We also arrived early enough to order food from Boat Drinks which we brought on the boat and enjoyed once sailing (allow enough time because Boat Drinks is not incredibly fast-- but worth it!). We already cannot wait to go sailing with Captain Conway again next year! read more

Travis B.

8 years ago

Nothing beats the sunset over the Chicago skyline! An A+ all around trip on the lake. I couldn't have asked for a better experience sailing with Conway - Not only was he super knowledgeable with the city and all things sailing-related, but the boat was very clean and he was prepared for everything including extra fleece jackets and blankets for us once the temperature dropped as the sun was setting! I have always preferred these sailing boats over the big cruise ships in Lake Michigan as they are way more personable with all the freedom to go where you want, but it feels good now that I finally have my go-to captain! read more

Kelly D.

8 years ago

Looking for a sailing trip for our thirteen year olds birthday, there were many options that we explored. We absolutely made the best choice with Captain Conway! The boat was meticulous and it was obvious that it was well cared for. He was incredibly knowledgeable and made the trip so enjoyable! Leading up to our trip, I had made an error in scheduling and he was quick to respond and very accommodating to ensure that we were able to get the sail in. There will be no need to explore options in the future - ChicaGo by Boat will be are one and only call! A wonderful time was had by all! I couldn't recommend him more! read more

Erin W.

7 years ago

I HIGHLY recommend ChicaGo By Boat! Captain Conway called 1/2 hour before to introduce himself and make sure we didn't have any last minute questions. We scheduled our tour for Saturday night (8-11P) to celebrate my mom's 60th birthday, and this tour did not disappoint. Captain Conway was knowledge about Chicago and gave us a great tour of the lakefront. We also had a front row seat to the Navy Pier fireworks. Captain Conway made us feel safe and welcome on his boat. He was social with us without being intrusive. I CANNOT say enough great things about this company! read more

Eric P.

7 years ago

My wife and daughters surprised me with this gift for my birthday and as a sailor myself this was a perfect gift. Beautiful scenery and perfect weather for sailing. The Captain and his First Mate were very accommodating and made the cruise all that much better. The boat is very comfortable and sails very smoothly. This is the perfect experience for anyone who wants to see Chicago from the water without the crowds. read more

Ken J.

7 years ago

I was able to take my girlfriend last Friday. This was the best date that we have ever had thanks to Captain Conway! The skyline was so perfect this night. Also, if you worried about getting cold. Don't! Captain Conway provides fleece jackets to keep you warm. The captain was also very knowledgeable of Chicago. The boat was spotless. Everything was perfect. Thank you for a wonderful evening! read more

Vincent O.

5 years ago

Came across Captain Conway and Chicago By Boat by accident, but boy am I glad I did. I took my gf for a surprise sailboat ride for her birthday and it was amazing. Capt. Conway was accommodating, friendly, personable, and made our first time on a sailboat an unforgettable experience. If we do this again with friends or family, I will be booking with him and his company again! read more

Keyatta O.

8 years ago

The sail on a Friday afternoon was picture perfect. The boat was comfortable for my small group of two and Captain Conway was very accommodating. We were able to bring our own food and drink onboard. I recommend this tour for anyone looking to get out on the lake and experience Chicago from a different perspective. Absolutely beautiful! read more

J P.

8 years ago

We had a really nice time with Captain Conway on a morning sail with perfect weather. He always called us back promptly when we left questions on his voicemail and had no problems arranging the charter. He was friendly, fun to talk to and the boat was very well maintained! Will book ChicaGo By Boat again if we do another sail! read more

Kiki K.

8 years ago

We had such a wonderful time on Captain Conway's sailboat!!! He and Tatiana made our Air and Water Show experience amazing. The boat was awesome and they both made us have a lovely time on Lake Michigan. We will definitely keep ChicagGo by Boat in mind for our next outing on the water!! Thanks again!!! TWO Big thumbs up!! read more

Brandon K.

8 years ago

We really enjoyed our time on this boat. I've done a few charters in Chicago, and this was by far my favorite. The boat was beautiful, well maintained, and comfortable. Captain Conway was knowledgeable, friendly, and made the experience really enjoyable. Highly, highly recommend. read more

Marcie H.

7 years ago

We truly enjoyed our experience. It was our first time sailing on Lake Michigan and Captain Conway did not disappoint. He was very personable and a great host. The views were beautiful. We felt comfortable and had a great time! We will definitely be returning! read more

PK M.

7 years ago

Captain Conway was top notch! Proposed to my now fiance on the charter, and Captain made sure everything went as planned. Very personable, professional, and accommodating. He also knew exactly where to stop the boat for the fireworks. Well worth the price! read more

Eric S.

8 years ago

Captain Conway was as good as Captain as one would need for an enjoyable day on the water. This from a 40 year deepwater sailor on the Great Lakes. I am sure under any circumstance that you will enjoy the trip and return safely. Nice clean comfortable boat!!! read more

Linda S.

7 years ago

We have sailed with Captain Conway several times. His expertise fills you with confidence. His personality is laid back. I would recommend ChicaGo by Boat to everyone. Sailing Lake Michigan is an experience everyone should have when visiting Chicago. read more

Daniel C.

8 years ago

Had a fantastic time out on 'Night Swimming'! The boat is a good size and held us comfortably. Captain Conway sailed us around the area with ease! Really enjoyed our time out on the boat and will be doing it again! read more

Nicole S.

5 years ago

We had a totally magical time with Captain Conway for a surprise proposal! Beautiful ship, excellent sailing and all around a truly wonderful time. We will definitely book again for other celebrations! read more

Conway B.

8 years ago

Have used the services of Conway Bennett in the past while he captaining other sailboats. Looking forward to the experience on his new boat. Evelyn Selvaggio read more

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More businesses like ChicaGo By Boat

Wendella Tours & Cruises

Chicago Architecture Center

Shoreline Sightseeing

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Trending businesses in ChicaGo By Boat's area

Waterfall Glen Forest Preserve

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21 ChicaGo By Boat reviews that are not currently recommended

Why does Yelp recommend reviews?

21 reviews that are not currently recommended

ChicaGo By Boat - boatcharters - Updated July 2026

Best of Chicago

People found ChicaGo By Boat by searching for…

Trending Searches in Chicago, IL

Browse Articles

Browse Nearby

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Related Cost Guides

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