sailboats in chicago

Take Advantage of Spring Savings!

Published February 20, 2024 read more

Chicago’s Sailing Standard Since 1978 Celebrating 46 Years of Service!

Serving today’s active sailor, Fairwind Sail Charters is Chicago’s oldest American Sailing Association sailing school and premier Sailing Yacht Lease Share Program where you can sail your own yacht all season long for a fraction of what it costs to rent or own. Beautiful yachts, unparalleled personal service, and the best rates anywhere have made Fairwind Sail Charters the choice of Chicagoland sailors for sailing instruction, sailing lease share, and private sailing charters for over four decades.

Haven’t you waited long enough? Getting started in sailing can be a daunting and expensive endeavor, but with Fairwind Sail Charters you get a legacy of friendly, straight-talking folks dedicated to making your sailing dreams a reality. Since 1978, Fairwind Sail Charters has set the standard for Chicagoland sailing, providing the best in quality, value, and service.

Best boats, best service, and best location equals the best value in sailing … anywhere!

Located at Burnham Park Harbor in the heart of Chicago’s famed Museum Campus, Fairwind Sail Charters’ legendary Dragon Fleet features BENETEAU YACHTS with direct walk-on access and ample parking right beside your yacht. With Fairwind Sail Charters, you park, step aboard your yacht, and sail away — that’s the Fairwind Difference .

One of Chicago’s oldest and most respected sailing schools, Fairwind Sail Charters offers award winning American Sailing Association sailing lessons leading to ASA sailing certifications from Basic Keelboat Sailing through Bareboat Charter and Advanced Coastal Navigation. Whether novice or old salt, Fairwind Sail Charters is dedicated to providing you the best sailing instruction to ensure a lifetime of safe and happy sailing.

And when you just want to kick back and enjoy one of the world’s most spectacular sailing venues, Fairwind Sail Charters offers private sailing charters for you and your guests with experienced Master Captains at the helm.

Please take a moment to cruise through what Fairwind Sail Charters has to offer. See for yourself the Fairwind Difference .

If you’re looking for Great People and Great Boats for Great Lakes sailing, join the hundreds of sailors who have made Fairwind Sail Charters their home port!

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SAIL LOFT CHICAGO, ILLINOIS, US

North Sails is the world's premier sailmaker for racing and cruising sailboats. Since opening our first sail loft in 1957, we have been the number one new sail choice for world-champion racers, superyachts, one-design sailboats , catamarans, trimarans, and casual cruisers. New sail options range to cater to any sailing adventure or budget. We look forward to welcoming you to our sail loft in Chicago, Illinois. Contact our experts to learn more.

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The North Sails team understands the importance of having top-quality sails that optimize your boat's performance. Our extensive range includes mainsails, jibs, genoas, spinnakers, and more, all meticulously crafted using advanced materials and cutting-edge technology. Whether you're racing competitively or cruising leisurely, our sails are designed to deliver superior speed, control, and durability.

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Our loft team are your local experts to tap into the innovation and resources available throughout North Sails' global network. These qualified sailors and sailmakers offer advice and help, which are equally important to the sails we sell.

North Sails is the premier sailmaker for all  racing  and  cruising  sailboats. We are the number one new sail choice for world-champion racers, superyachts,  one-design sailboats , catamarans, trimarans, and casual cruisers. New sail options range to cater to any sailing adventure or budget. 

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Chicago's best boats and yacht charters, we have two of the best private charter party boats in chicago.

We offer two beautiful powerboats that can take a total of 25 people out together on Lake Michigan. A 51′ Searay Sundancer and a 35′ Searay Sundancer boat that can accommodate a lot of guests. We can bring both of our boats together so you and your entire group can do a “Tie-Up in the Playpen”. Summer in Chicago without spending time with all your friends in the Playpen should not be missed. Please book your group trips early before we get all booked up

Charters can range from going to the world-famous “playpen” where we can anchor and crank up the sound system and go for a swim or chill on our rafts to cruising along the lakefront and by navy pier. you can also take a trip through the “locks” and down the chicago river or some blue water cruising past the chicago lighthouse, the cribs of chicago, and into the deep blue waters of lake michigan and taking in some of the best views of chicago.

Chicago Sailboat and Yacht Charters provide our guests with exclusive, private charters that offer complete luxury, flexibility, and customization. Take your friends & family on a cruise and experience Chicago like you never thought was possible a priceless adventure.

On wednesday & saturday nights we offer sunset & fireworks cruises just off of navy pier., experience firsthand the relaxing beauty of a peaceful sail on our 4+ hour and all day private boat charter. boating in chicago is the perfect way to end the day with friends. maximum of 12 guests on a boat., come enjoy the beauty of chicago in the lap of luxury. our lake michigan boat charters include many points of interest around chicago such as: the playpen, navy pier, chicago river locks, chicago lighthouse, adler planetarium, shedd aquarium, soldiers field, buckingham fountain and many more., chicago yacht rentals - a unique way to explore the city, our cruises are perfect for these special occasions:.

• Bachelorette or Bachelor Parties
• Anniversary Cruises
• Special Occasions Cruises
• Chicago Scene Boat Party
• Birthday Parties
• Corporate events
• The World Famous “Playpen” we anchor, turn up the music, crack open the drinks and dive into the water
• Chicago River Cruise – Hanging out at City Winery
• Chicago Air & Water Show (Friday, Saturday & Sunday middle of August)
• Holiday Weekends (Memorial Day, 4th of July, and Labor Day- Book early they book up fast)
• Lollapalooza- Listening to the concert from Monroe Harbors

51′ Sea Ray

You can also find our website at BoatCharter.info

35′ sea ray.

Private, Luxurious, and Affordable Yacht Charters in Chicago, IL

Bring a group to party in the playpen, the playpen - chicago's popular boating place.

The luxurious amenities on our boat will amplify your experience as you feel the breeze blowing through your hair. The dazzling blue waters are ideal for swimming, and you can even climb aboard a floating island to take a break from all the action.

Whether you’re looking for some relaxation or some excitement, the Playpen is the ultimate destination for boating enthusiasts.

Chicago Sailboat and Yacht Charters Offer Priceless Pampered Yachting Experiences

At Chicago Sailboat and Yacht Charters, we pride ourselves on providing our guests with priceless, pampered yachting experiences. We go above and beyond to offer complete luxury, flexibility, and customization, tailoring each of our charters to your unique desires. From taking a cruise down the Chicago River to partying in Lake Michigan’s Playpen to watching the sun go down over the city, our yacht charters will help you do it all in style. At Chicago Sailboat and Yacht Charters, we believe that our guests deserve the absolute best, and we promise to deliver unforgettable, priceless yachting experiences that you’ll treasure for years to come.

WHAT PEOPLE SAY ABOUT US

Check out the Testimonials page to see what people are saying about our boat charters.

The views of the Chicago skyline were amazing, we can't wait to go again!

The captain made our trip really fun and educational seeing all the different sights like Navy Pier with its flags flying high was incredible and the views of the Chicago Lighthouse and water Intake cribs up close were amazing.

Our family had an incredible time sailing on Lake Michigan

The Fireworks by Navy Pier were incredible especially watching while having dinner and a good beer

1300 S Linn White Dr, Chicago, IL 60605

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Choose Windy City Sailing for your Chicago Sailboat Charter

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LUXURY ACCOMODATIONS

Our sailing yachts accommodate 1 to 10 people. We offer charters with captain and crew for groups up to six (6) or a bareboat charter for groups up to ten (10) with a USCG Licensed Captain paid separately. With up-to-date amenities and two bathrooms onboard, we assure the comfort of all our guests.

CUSTOMIZED CHICAGO SAILING CRUISES

All private Chicago sailboat charters depart and return according to your schedule. All Chicago sailboat cruises have three-hour minimums. Charter extensions are available upon request. Yes, we encourage you to bring food and refreshments, including alcoholic beverages.

Our yachts are professionally maintained and equipped.  In addition, we certify, train and employ United States Coast Guard Captains with over 20 years of experience. Because of this, rest assured that you are in excellent hands.  Also, all of our captains are enrolled in USCG mandated drug screening programs.

CONVENIENCE

The yachts are at the North End of Belmont Harbor, just east of Wrigley Field—or 15 minutes from the Chicago Downtown area. Windy City Sailing is easily accessible via Uber, Lyft, taxis, and bicycles. Also, parking is available via the City of Chicago. Gift certificates are available for all Chicago sailboat cruises and bareboat charters. We confirm reservations with a 50% deposit, fully refundable with a seven-day notice. Gratuity is at your discretion (we recommend 20% to our outstanding crew).

SPECIAL EVENT YACHT CHARTERS

4th of July Sailing Charter

​ Each year, the Fourth of July Sailing Charter gives the citizens of Chicago the chance to witness some of the nation's most spectacular firework displays from the comfort of a boat. The tour has become increasingly popular and is one of the highest rated Independence Day activities.

Chicago Air Show Charter

​ Chicago Air and Water Show is a remarkable event that has long been captivating city dwellers. By taking a sailboat charter from us, you can experience the show from the lakefront. You won't need to fight the crowds for the best view, as you will be luxuriating on your yacht with an unparalleled outlook of the show.

Navy Pier Firework Charter

​ During summer, the Navy Pier gives us breathtaking firework shows. For an unforgettable experience, there is no better way to appreciate these amazing visuals than to charter a yacht . Our dedicated captains and crew members make sure that all your needs are taken care of, so you don’t have to worry about anything else. With our exclusive amenities, it is not even worth considering any other way to view these displays.

Book Your Chicago Sailing Trip Now

WITH WINDY CITY SAILING

We know you will have questions about sailing charters, so feel free to reach out via phone or email.

Please contact Edwina at 773.868.0096 or  [email protected]  for details and pricing.

Frequently Asked Questions

Have you ever wanted to sail but were unsure what it would cost to charter a private yacht? If so, Windy City Sailing is here to help with all your sailing–related questions. We have made things easy to find by categorizing our questions, and if there’s anything you can’t find, feel free to reach out. Our knowledgeable staff is here to answer all your questions about sailing along the wonderful Chicago Lakeside. From planning the perfect corporate outing for out-of-town guests to helping you witness the incredible  4th of July fireworks , we have it all covered!

Review our  FAQ

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Preferred Partners are the resources we depend on to deliver the highest quality service to our guests. We value them and appreciate their services.

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Chicago Yacht Works (CYW) is your one-stop shop for all things boating. Whether you are a new or experienced boater, we work hard year-round to make sure you enjoy your time on the water. CYW offers indoor/outdoor storage, certified service technicians to maintain your vessel as well as an accredited school, Chicago Yacht Academy, for boating education and certifications.

Buying or selling your boat?   No problem. We are one of the Midwest’s largest brokers and home of the Formula Factory Showroom. CYW provides plenty of inventory for your viewing pleasure and we’re happy to add your boat to the list, if needed.

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Unforgettable views. Unparalleled experiences.

Cruises & Tours

Explore chicago by land, water or air.

Whether you’re in town for just one day or are a life-long resident, cruises and tours of Chicago are a great way to see the sights, discover something new, or treat yourself to an unforgettable experience.

From laid-back sightseeing cruises and elegant dining cruises to heart-pumping thrill rides to upscale private charters, Lake Michigan and Chicago River cruises departing from Navy Pier offer a memorable experience for all.

Our Cruises & Tours

Architecture & Sightseeing Cruises

Take in Chicago’s iconic skyline and the scenic Chicago River with sightseeing cruises at Navy Pier! These fun experiences offer guests panoramic city views along with entertaining and enlightening commentary about Chicago’s architecture and history.

Brunch, Lunch and Dinner Cruises

When you dine on Like Michigan, every table is the best in the house. Navy Pier’s brunch, lunch and dinner cruises pair world-class cuisine with panoramic views of the city and lakefront.

Speedboat Tours and Thrill Rides

This isn’t your parents’ leisure cruise! On these 30-minute speed boat rides, you’ll tear across Lake Michigan at up to 45 miles per hour while getting entertaining and informative commentary on Chicago.

Specialty and Holiday Cruises

There’s always something worth celebrating with cruises on Lake Michigan and the Chicago River. Our partners offer themed cruises for major holidays, as well as a wide variety of special events that are sure to get you in the party mood.

Groups And Private Charters

Perfect for corporate outings and special occasions, group cruises and private charters offer unforgettable experiences for up to 800 guests.

Bicycle Tours

Bike & Roll Chicago allows guests to rent bicycles for a fun experience on the lakefront.

Cruise & Tour Types

Shoreline Architecture River Tours

Take Shoreline’s award-winning 75-minute Architecture River Tour to discover Chicago’s renowned landmarks as presented by our expert and entertaining guides. You’ll learn how Chicago rose...

City Cruises – Premier Dinner Cruise on Lake Michigan

Lake Michigan dinner cruises are the perfect setting for celebrating with friends, connecting with colleagues, or a romantic evening. Odyssey Lake Michigan dinner cruises are...

City Cruises – Premier Lunch Cruise on Lake Michigan

A two-hour Lake Michigan lunch cruise is the perfect way to enjoy time with family or the company of great friends. Retreat from a busy...

City Cruises – Signature Dinner Cruise on Lake Michigan

Celebrate a special occasion, host a group event or share a romantic evening aboard Spirit of Chicago. Great for parties of all sizes, a Spirit...

City Cruises – Spirit of Chicago Dinner Cruise

Catch the Chicago skyline at sunset during the most beautiful time of the year, and join us for a fun, laid-back, 2-hour cruise. Spirit's Lakefront...

City Cruises – Odyssey Lake Michigan Dinner Cruises

Odyssey Lake Michigan presents special prix fixe dinner cruises, offering guests the opportunity to try one of Chicago’s most unique dining experiences at an incredible...

City Cruises – Spirit of Chicago Brunch Cruises

Whether you’re a native Chicagoan, newcomer, or just visiting, a Spirit of Chicago brunch cruise is the perfect weekend outing. See well-known Chicago attractions from...

City Cruises – Signature Lunch Cruise on Lake Michigan

With the sunshine reflecting off the lakefront, there’s no better place to enjoy an afternoon in Chicago than aboard a lunch cruise. Departing from Navy...

City Cruises – Seadog River and Lake Architecture Tour

Enjoy Chicago’s iconic skyline with an exciting architecture cruise on the Chicago River. Departing from Navy Pier, this 75-minute narrated cruise is the best way...

City Cruises – Seadog Lakefront Speedboat Tour

Our Lakefront Speedboat Tour is the best way to view Chicago from the lake, combining an exciting speedboat ride along the shoreline with informative and...

City Cruises – Seadog Extreme Thrill Rides

With exhilarating high speeds and full 360° spins, this jet-propelled ride blasts off to start and splashes down to stop. Experience full throttle slalom runs,...

City Cruises – Odyssey Lake Michigan Brunch Cruise

This two-hour brunch cruise on Odyssey Lake Michigan, departing from Navy Pier, is ideal for capping off an incredible weekend. Enjoy a delicious menu stocked...

City Cruises – Odyssey Lake Michigan Groups

Host a truly unforgettable event on Lake Michigan. Book your group aboard one of Odyssey's regularly scheduled lunch or dinner cruises, or have an event...

Shoreline Sightseeing Group Tours

Adventures are meant to be shared. Turn your next family gathering or corporate outing into an awesome adventure by booking with Shoreline. We offer special...

City Cruises – Chicago Elite Private Events

It's your yacht. Let our professional event planners create a custom event just for your group aboard the Chicago Elite. With two fully enClosed ,...

City Cruises – Seadog Groups

Planning a special outing for your group? Charter Seadog for an event everyone will enjoy! With the ability to travel both the lake and river,...

Shoreline Sightseeing Water Taxis

Shoreline Sightseeing’s water taxis are a great way to get around town. Starting in May and running through September, our water taxi service offers fast...

City Cruises – Spirit of Chicago Group Cruises

Host an event unlike any other in the city! Book your group aboard one of Spirit’s regularly scheduled lunch, brunch, cocktail or dinner cruises, or...

City Cruises – Premier Brunch Cruise on Lake Michigan

Experience the city’s most unique floating event venue! City Cruises offers all-inclusive packages, chef-prepared menus, full bar options, and entertainment customized to fit your needs—all...

City Cruises – Signature Brunch Cruise on Lake Michigan

Shoreline Skyline Lake Tours

Shoreline’s 40-minute Skyline Lake Tour offers a relaxing way to experience the panoramic of the city’s famed skyline as seen from majestic Lake Michigan. The...

Tall Ship Windy Chicago Skyline Sail

Tall Ship Windy is closed for the season and will reopen in May 2024. Visit the Tall Ship Windy website to stay up to date...

Tall Ship Windy Private Charters & Weddings in Chicago

A Beautiful Stage for Your Event Set sail on Windy for weddings, parties, corporate functions, reunions, church outings, tour groups, team building and more! Windy...

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Chicago, IL

boating guide

In addition to the best offers we have for boat and yacht charters in Chicago, IL, see also options available for rent in these nearby locations:

• 19 boat rentals in Chicago Loop, Chicago, IL
• 19 boat rentals in Chicago, IL
• 19 boat rentals in Near South Side, Chicago, IL
• 19 boat rentals in River North, Chicago, IL
• 19 boat rentals in Streeterville, Chicago, IL
• 19 boat rentals in Near North, Chicago, IL
• 19 boat rentals in Little Italy, Chicago, IL
• 19 boat rentals in West Loop, Chicago, IL
• 19 boat rentals in Near North Side, Chicago, IL
• 19 boat rentals in Gold Coast, Chicago, IL

Rent a Sailboat Charter in Chicago, IL from Sailo!

Looking for a sailboat rental in Chicago, IL? Discover Chicago by a private sailboat yacht charter with Sailo. Enjoy a whole other side of Illinois on a sailboat rental in Chicago with captain, or skipper yourself if you prefer. Whatever your boating needs, you’ll find the perfect sailboat for your Chicago sailing trip, party or special event. Enjoy sunset cruises, watersports or fishing trips, or a day out with family and friends for a memorable experience on a Sailo boat.

Our premium inventory of private sailboat charters in Chicago, IL

Chicago, IL is a well-known boating destination in the US, perfect for a memorable experience on a Sailo boat. The sailboat rentals are popular for both locals and tourists and a great choice if you want to spend some quality time with your family or friends. 16 charters are currently available with or without captain, lined up in the Chicago’s marinas, waiting for their guests. Rent a private sailboat in Chicago with Sailo: it’s easy, quick, secured and the best choice for a fun experience in the waters of Illinois.

How to find the perfect Chicago sailboat charter?

How to rent a sailboat in Chicago, IL? Sailo has the most advanced filters to help you find the perfect sailboat rental in Chicago, Illinois for an amazing experience on the water. Start your search by choosing your start Chicago sailing trip date, duration and number of guests. For a great day trip with your family or friends, you have the option to select 2, 4 hours or full day rentals. Depending on your preferences and budget, you may narrow your results by boat type and price range. The 'crew' filter allows you to check the boat rentals with the captain included in the price, skipper optional (paid as extra) or bareboats that you’ll captain yourself (boating resume required). Once you have laid your eyes on a boat you like in Illinois, click on it to read the description, reviews and see more pics. We also recommend using our direct 'Message Owner' feature that allows you to start a conversation with the boat representative to ask away everything you want to know before you submit a booking request.

How does it cost to rent a sailboat in Chicago for a day?

Whether you are looking to rent a yacht for a city sightseeing tour, a romantic sunset cruise or an active day on the water with your family or friends, we're confident you’ll find the best one for you on Sailo. The average starting price to charter a sailboat in Chicago is $1100. You can however find excellent affordable rentals from $250 and also elegant Chicago sailboat yacht charters that can go up to $6500 (service fee and mandatory extras not included).

Essential safety tips for recreational boating

Whether you’re renting a boat with captain or you choose a bareboat, always keep in mind this basic safety guidelines:

• if you rent a captained charter, always pay close attention to your captain
• walk slowly and never run onboard as you can easily slip and fall overboard
• be mindful of stairs and hatches (never step on them)
• if you go swimming, floating or paddling, stay away from other boats even if they are anchored or moored
• pay attention to the other group members and make sure that everybody is accounted for at all times

Sustainable yachting tips

If you’re looking to start Chicago sailing, a sailboat charter is a great place to start! Explore coral reefs with your snorkel, discover hidden bays and islands and generally enjoy the view of nature. Remember, that sailing motto: 'Take only photos, leave only wake' (OK, so we paraphrased). To be a responsible sailor, remember:

• Don’t disturb coral or sealife
• Take your trash home (and don’t throw anything in the sea)
• Respect the locals and their customs wherever you go

Read more about responsible boating.

Popular locations to rent a boat on the Midwest USA:

• Rent a boat in Detroit
• Cleveland yacht charters
• Michigan boat charters
• Rent a boat in Ohio
• Traverse City boat rentals
• St Clait Shores boat rental

Popular boat types among renters:

• Chicago party boat rental
• Chicago catamaran rentals
• Motor boat rentals in Chicago
• Party boat rental Detroit, Michigan
• Cleveland sailboat rental
• Party boat rental Cleveland, OH
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DAYTIME SAILBOAT & YACHT RENTAL IN CHICAGO, IL

The late spring and the summer months are ideal for scheduling a daytime private sailboat & yacht rental in chicago., daytime sailboat & yacht rental in chicago,il.

Renting a sailboat or yacht from Chicago Sailboat Charters is a fantastic way to experience the beauty of Lake Michigan and the stunning skyline of Chicago. With a range of sailboats and yachts available, accommodating different group sizes, you can enjoy a private charter with captain and crew or opt for a bareboat charter for a more independent sailing experience.

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• Regatta Series

Thrilling Big-Breeze Start to Regatta Series in Chicago

• By Dave Reed
• June 7, 2024

PRELIMINARY RESULTS

PHOTO GALLERY

Cliché as it may sound, the Windy City indeed lived up to its reputation on the opening day of the Helly Hansen Sailing World Regatta Series in Chicago, hosted by Chicago Yacht Club with more than 150 race teams participating. The warm bright morning sunshine and the blocking of the architectural giants of the lake front may have duped many of the competitors into thinking conditions were benign as they slipped their lines this morning. But out on the open water, northwesterly gusts peaked into the high 20s, catching many teams off guard. The day was good fast sailing for some, while for many others today’s races were all about the preservation of gear, sails and crew. 

Those who were willing and able excelled in the gusty conditions, however, including Richard Stearns’ team on the J/105 Five . They won the day’s only race for the 105s, and while others in their fleet played it safe by sailing runs under main and jib only, Stearns’ crew had no trepidations in setting the spinnaker. “There were four strong women keeping everything going at the front,” said crewmember Lindsey Hernandez. “We didn’t wipe out once, and the driving was perfect.”

Stearns, a veteran helmsman, has plenty of experience in all conditions and was happy with the team’s performance. “It was all having them pulling the sails around perfectly timed,” he said. “I’m just following what they’re doing.” 

The J/105 class shared the White Circle with the Beneteau 36.7s and J/88 fleets. The J/88s were the first fleet start of the morning and as they were rounding their first weather mark, the forecasted wind increase came on fast, and quickly built into the high 20s. As soon as their spinnakers were full, boats were simultaneously wiping out. Daniel Burns, bowman on John and Jordan Leahey’s Dutch , confessed to three broaches for his time in one race—a personal record for him. “They were fun though,” he said. “We did it in style. We were surprised by the first one, but the next two we were like, ‘let’s just get this over with.’”

Using a smaller spinnaker for the day, Grace and Michael Gillian’s Julia won the J/88’s only race, finishing ahead of Andy Graff’s team on Exile . Dave Dennison’s Pirahna was third. 

Robert Nelson’s Beneteau 36.7 Free Radical beat Silviu and Cristina Petrea’s Nomad in their fleet’s only race. Earle Atwater and Chris Metcalf’s Program were third and happy to have survived the day with sails and boat intact. 

Atwater’s advice once ashore and safely in their slip at CYC, was to “remember to ease the lazy guy in the jibe,” to avoid the broach. That didn’t happen once, so for the remainder of the race, they sailed the runs under jib and main only. “We were safely in third so we figured,” Atwater said. “So, why blow it?”

The big boats of the Division 3 racecourse, set straight east of host Chicago Yacht Club, were fortunate to get in two races. Scot and Yvonne Ruhlander’s crew  on the Beneteau 40.7 Mojo , racked up wins in both races and begin the series with a 3-point lead over Thomas Weber’s La Tempete. Mojo was quick upwind and clean on the runs by eventually leaving the spinnaker in its bag. Weber’s team was equally quick upwind, but could not match Mojo’s pace. 

“We’ve been doing it a long time,” said Tempete, nonplussed with the wild conditions. “We kept it together, but we got it rocking pretty good in the waves at times. Upwind, once we got it in the groove and everything tuned well, it was pretty easy. On the first upwind leg I had some trouble on port tack, but on the next three upwind legs we got it dialed in really well. The main trimmer gave me more play on the main and we were able to keep our speed up.”

Raymond Douglas and Kristine Maybach’s crew on the J/109 Courageous also won both races and have a 3-point lead over Jim Caesar’s crew on Liquid Lounge II . Both teams managed their spinnakers well enough to capitalize on good starts. 

The collective experience of Shawn and Jerry O’Neill’s crew on the Sydney 38 Eagle had them confidently guiding their boat around the course. Careful sail handling and clean starts got them two wins on the day to lead the ORC division. The disappointing news from the ORC division was the dismasting of Phil Dowd’s Farr 40 Inferno . They’d finished second in the day’s first race, but halfway down the first downwind leg of the second race, while leading the fleet, the mast broke and had to be cut away and scuttled to prevent damage to the boat. 

Tod and Heidi Patton’s J/112e Blondie also went two-for-two in the PHRF spinnaker division and have a 3-point lead over Jim Banovitz and Gary Feracota’s Aria , a Beneteau Figaro 3 that was quite quick on under jib and main only. 

Only one race was sailed on the One-Design circle with Brian Kaczor’s Erica winning the Tartan 10 race, ahead of Adam Prettyman’s Two Trailer Park Girls and Amy Cermak’s Diamond Girl . Jim Murray’s Hestia was the top J/70, edging out Laura Sigmond’s Norboy and James Prendergast’s USA167 . 

The Laser divisions did not complete races due to the high-wind conditions, but will be on the water tomorrow along with the Distance Race divisions, with more than 30 teams getting underway in the early morning for what promises to be another challenging day on Lake Michigan.

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7 things that might surprise you about the Chicago Architecture Boat Tour

T here are plenty of ways to take in the sights, sounds (and smells) of Chicago, but you don't necessarily have to be on land to do that.

And you don't have to be a tourist, either.

In fact, one of the most beloved ways — among locals and visitors alike — to experience city is by journeying across the Chicago River and Lake Michigan while a tour guide talks about buildings and regales you on the untold story of Mrs. O'Leary's cow.

In other words: a Chicago Architecture Boat Tour.

"As you're going up and down the Chicago River and on Lake Michigan, you're seeing the city’s evolving architecture, which is changing every year" said Andrew Sargis, director of sales and marketing for Wendella Tours and Cruises .

Wendella, billed as Chicago's "original" architecture tour, in 1935 gave its first architecture tour of the city from a wooden diesel yacht out on Navy Pier, Sargis said. Now, upwards of 20 architecture tours are offered daily, with more on the weekends. On average, Wendella tours see roughly 100,000 passengers each month over the summer, Sargis said.

And though the majority of guests on any given Wendella architecture tour are tourists, Sargis said, locals take them, too.

MORE: Even Chicagoans can't get enough of this tourist attraction: ‘It's about the only touristy thing I do'

"I was surprised when I first started, we get a lot of repeat locals," Bobby Scheffle, a Wendella tour guide told NBC Chicago. "And always there's a lot of local people that come on when they have guests visiting them in town. They like to show off the city this way."

But there's something else about the experience that makes it so very Chicago.

"I think it is really unique to experience the city from a boat on a river, because we think about other big cities in the United States -- there aren't many that have a river that go right through downtown," Scheffle said. "You feel like you're in the city, you hear the noise, and you see the buildings and all that."

Whether you're taking the ride for the first time or the 50th, bringing out-of-town guests out for a memorable activity or just itching to be a tourist in your own city, here are seven things to know about the Chicago Architecture Boat Tour.

Will weather stop a tour from running?

Wendella's architecture tours run year-round, Sargis said, although "weather is a factor."

Weather events like ice on the river or significant snowfall can impact operations, Sargis said, but they typically don't, since the Chicago River -- a federal waterway -- must remain navigable year-round.

While Wendella's boats do have climate-controlled indoor lounges, tours during the winter may run at limited times. But rain, snow, extreme heat or wind, unflappable Chicagoans still show up.

"We went on drizzly day a few years ago," Kathy Rambo wrote on NBC Chicago's Facebook page. "There were only about 10 of us on the boat!

And most often, the tour will run — rain or shine — so don't hesitate to bring a raincoat.

"I have certainly [given tours] under thunderstorms and downpours, and I've gotten drenched sometimes," Scheffle said. "I've never had a tour get canceled because no one bought a ticket. There's always someone wanting to come out here in the rain or the cold."

What's the best time of year (or day) to go?

It depends on when exactly your favorite time of the year is, and what you're hoping to see.

For Sargis, it's late summer. "There's this point of time in September when the weather is beautiful, but there's not that summer rush."

There are other times that Chicagoans may want to consider, too.

"St. Patrick's Day Celebration when they dye the river, and any Wednesday or Saturday night [over the summer], watching the fireworks over Lake Michigan , especially if you're local" Sargis said.

During the summer months, Wendella's tours run start as early as 9 a.m., with the day's final tour not ending until 10 p.m. or 11 p.m., Scheffle said, "so if you want to come for a ride to see the city lights, you can come late, and it's also beautiful, just a little more difficult to see the colors on the buildings if that's what you want to see."

Laura Pubins, who lives in a suburb outside of Chicago, agrees.

"My favorite one was when we were on a boat at sunset," Pubins wrote to NBC Chicago on Facebook. "It was an awesome new view of the city."

What's the most photogenic spot on the tour?

For Sargis, it's "anything out on Lake Michigan," with the skyline in the background.

On the river though, there's one moment that captures the city best, Scheffle said, no matter what time of day you're taking the trip.

"The best place to take a photo on the 90-minute river tour is when we come up the south branch from Chinatown," Scheffle said. "That's the best place because you get the whole skyline from the south. It's really beautiful."

For locals though, it may not be what you're looking at, so much as how you're looking at it.

"You're looking at [the city] from underneath," said Chicago resident Nick Pappas, 55, who recently found himself on a 90-minute river tour. "It's just a different perspective on the river that you don't get on the street level. As amazing as that sounds, you're only, like, 20 feet down, but it gives you a whole different perspective."

What does the training for a tour guide look like?

According to Sargis, all Wendella tour guides are trained in-house -- and the spots are competitive.

"There's high demand," Sargis said, of the position. "There are more people that want to be tour guides than space available. It's certainly a popular job, and people want to do it." While the tour guide of any given architecture tour isn't made public, many people do request certain ones for private events, Sargis said.

For the tours, there's a general script, with highlights that must be mentioned, Sargis said. But improvisation, along with sharing personal history is encouraged, too.

"All of the tour guides have their own experience in the city, and will add parts of their history in it," Sargis said. "We have a tour guide that is a retired police officer, and he will interject anecdotes form his career. We have a tour guide that's a Vietnam War Veteran, and when we go by the Vietnam War Memorial, he will always discuss the importance of it to him."

For Scheffle, the training included joining multiple tours a week for two weeks and flashcards.

"For a while, I, just drove Uber and Lyft," Scheffle said. "And then, I remembered that I really liked Chicago. I like learning fun facts about it. And there are people in the city that have that as a job -- to tell people fun facts about Chicago and I started looking into tourism jobs in the city."

What's the most common question tour guides get?

Believe it or not, it's not always about The Great Chicago Fire , or Mrs. O'Leary and her cow, at least on Scheffle's tours.

"My favorite thing on the tour that happens is probably when little kids ask questions," Scheffle said. "The common question that a kid will ask, because I talk about the tallest building, second tallest building, third tallest building, a lot of times a kid will ask what's the shortest building in Chicago? Which I don't have a good answer for."

Are you supposed to tip your guide?

"It's up to the discretion of the client," Sargis said. "I would say a lot of our passengers do tip our tour guides."

What's the absolute best part of the tour?

Sure the tour is photogenic, and the city's history is fascinating. And though some may go on the tour to find out what buildings are new, others prefer to think about the old.

"My favorite building to talk about is probably the Board of Trade building," Scheffle said. "Just because I remember walking by it much younger and always, I remember, really being impressed by it, thinking was such a cool big city building."

For a local on the tour, the memories are nice. But a day out on the water in Chicago is just hard to beat.

"It's great. I don't have to work," said Pappas, who has lived in the city for 55 years. "Every time, it's a little treat to go down the river."

Video editors Ivonne Ramirez and DS Shin produced and created the video for this story.

CPD marine unit rescues 2 boats that caught fire on Lake Michigan

Chicago police marine units responded to a distress call near east 50th street and dusable lake shore drive about 9:30 a.m. sunday and found a boat on fire, police said. three passengers were rescued, and the fire was put out. a second boat was rescued later sunday..

The Chicago Police Department marine unit tows a 60-foot boat named Misfortune that caught fire on Lake Michigan on Sunday.

Courtesy of CPD

Two boats caught fire on Lake Michigan on Sunday, Chicago police said. No injuries were reported in either incident.

Chicago police marine units responded to a distress call near East 50th Street and DuSable Lake Shore Drive about 9:30 a.m. and found a boat on fire, police said. Three passengers were rescued, uninjured, and the fire was put out.

The second incident of the day concluded when CPD’s marine unit was able to locate a 60-foot boat named Misfortune, which had mechanical issues due to a fire. The vessel was towed back to Burnham Harbor. None of the eight passengers were injured.

#ChicagoPolice @CPDMarineUnit responded to 2nd #boat #fire of the day on #LakeMichigan . Fortunately M3 was able locate the 60ft #vessel MISFORTUNE. Due to the fire the boat had mechanical issues. M3 safely towed her & 8 passengers into #BurnhamHarbor . #Chicago #ChicagoLakefront pic.twitter.com/Tg6UzJdxSp — Chicago Police Marine Unit (@CPDMarineUnit) June 3, 2024