Sean D. Tucker flies an Oracle Extra airplane over downtown Chicago, where America’s Cup racing will be held this weekend. Organizers are hoping the city has better wind and a better viewing experience than New York last month. (Kiichiro Sato/Associated Press)

Call them growing pains. As the America’s Cup attempts to increase its reach to spectators and television audiences, organizers are grappling with challenging conditions both natural and man-made, making hosting the racing series a work in progress.

Administrators are trying to learn from last month’s event in New York as they sail this weekend in Chicago, the second and last America’s Cup stop in the United States before it moves toward the final events next year in Bermuda.

Six teams will compete Saturday and Sunday in AC 45 foiling catamarans, $10 million Kevlar-and-carbon-fiber crafts that look more suitable for space than sea. Tens of thousands of spectators are expected.

Last month’s America’s Cup racing in New York, while visibly stunning and attended by a reported 100,000 people, had critics complaining that the two-day contest left spectators confused, sailors frustrated and audiences at home bothered by NBC’s coverage.

The America’s Cup series carefully selected host-city locations close to the shore, where fans could watch the races as part of a larger trend toward inshore sailing competitions to grow crowds and interest — and in an ongoing effort to break from elitist labels and push deeper into a mainstream fan base.

There are certain challenges to inshore racing, however, with a fine line between presenting a quality venue for racing with good conditions and a successful experience for spectators at the race and at home.A good show is important, but the series is still a competition: Points matter and go toward the America’s Cup final. Some critics contend that optimal conditions are being sacrificed in the rush to grow the sport and boost visibility.

“It’s a challenge,” said Todd Harris, the America’s Cup broadcaster for NBC. “Just look at what Mother Nature threw at us in New York.”

Sailing fleet races can be difficult to follow. Most fans lined along the Hudson River in New York, while impressed with the show of winged foiling catamarans gliding at times midair above water a few boat lengths off shore, seemed confused and unable to follow the action on the water in the absence of any announcers explaining race coverage.

On the first day of racing in New York, there were strong currents and little to no wind. Boats drifted off course down the Hudson as spectators scratched their heads wondering whether this was the actual race. An hour passed before many realized the race had been cancelled.

In Chicago, meanwhile, spectators will have LED screens in the field of vision where they can simultaneously watch the boats on the water and the action on the screen.

For sailors, complaints were mostly about the location of the race course on the Hudson, between buildings in downtown and Jersey City. The location provided great viewing for spectators but less than ideal wind for sailing.

“The last place on earth you would want to put a race course,” Olympic sailor Ben Ainslie said after the weekend races in a column for the Telegraph. “Racing was about as frustrating as it gets.”

Conditions will be significantly better in Chicago. Buildings are further inland along the shoreline, and sailors will not have to contend with ocean currents or tides. New York might have been the most restricted venue for America’s Cup racing, according to Ken Read, an NBC analyst and professional sailor. Chicago is much more wide open.

Also, the wind might be better. “If you had to bet on good conditions between New York in May and Chicago in June,” Read said, “Chicago would win hands down.”

In the meantime, broadcasting a live sailing event is a tough job. Sailors have the flexibility to wait for good racing conditions. A live television broadcast has a fixed window.

Televisions audiences were frustrated with NBC’s coverage of the races in New York that often went to commercial at pivotal moments. Critics say the network poorly placed its two three-minute commercial blocks during each of the 15- to 20-minute races — leaving anyone watching lost. The mishap was almost comical: Imagine watching a baseball game with the bases loaded, batter up, bottom of the ninth . . . and a beer commercial comes on.

That feedback was heard, according to Tod Reynolds, an America’s Cup event coordinator. “It’s something America’s Cup is working on,” he said. “New York was the first time we’ve had live racing in the current format. It’s tight. You don’t have much time to cut away. Hopefully Chicago will be better than New York. We’ll continue to improve as we get closer to Bermuda.”

Invariably, there are breaks during crucial action. “It’s going to happen,” Harris said. “There are commercial obligations. These are expensive events. They don’t come here and sail for free.”

Weeks later NBC aired a spectacular and informative one-hour highlight show of the New York races, with seamless commentary and recaps.

As in New York, Chicago will have a bit of celebrity added to the races. As part of public-outreach efforts to boost America’s Cup visibility, organizers invited celebrities Lindsey Vonn, Stephen Colbert, Sir Richard Branson, Jason Biggs, Mark Ruffalo and Liam Hemsworth to sail with teams during practice. In the U.K., Kate Middleton has lent America’s Cup some royal sheen and sailed with Ainslie’s Land Rover team as an ambassador. She also runs a charity set up by Ainslie’s sailing team that provides nautical training and youth education.

Chicago organizers were forced to scrap celebrity sailing during the week but promised some big names would be on the water over the weekend.

The racing will take place on Lake Michigan off Navy Pier and in fresh water for the first time in race history. Harris thinks boats could foil differently, perhaps faster. Read says there will be no noticeable difference. Reynolds, citing viscosity, said it might be the perfect opportunity to set a new competition speed record.

The current mark is 32.8 knots.