Growing up in Chicago, I remember hearing stories of the architectural feats required to build the Sears (now Willis) Tower and the John Hancock Center, two of the tallest buildings in the world.

Huge X-shaped braces, for example, were needed to absorb the biting winds that blew in from Lake Michigan.

And there were surprises once people moved in. Residents of the highest floors in the John Hancock sometimes had to call their doormen to ask about the weather because their apartments were above the clouds.

What is it that drives some people to live so high up? And developers to keep building ever-taller edifices?

New York, it seems, is entering a tall-buildings arms race. By 2016, New York could have 6 of the 10 tallest buildings in the country (with Chicago having the other 4), and 3 of the highest residential structures, according to the Council on Tall Buildings and Urban Habitat in Chicago.

Following New York by Gehry at 8 Spruce Street and the mammoth One57 at 157 West 57th Street, even taller residential towers are in the works, including 432 Park Avenue on the site of the former Drake Hotel, and the GiraSole, proposed for 11th Avenue on the Far West Side.

Both of those buildings would be taller than One57, which will be Manhattan’s tallest residential building, at 1,004 feet, when it is completed next year. And 432 Park Avenue, a condo structure scheduled to be finished in 2016, would be 1,398 feet, surpassing One57 and second in height only to One World Trade Center, an office complex, the Council on Tall Buildings said.

Then there is 1214 Fifth Avenue, which is being pitched as the “tallest residential building on the Upper East Side,” though it is actually in Harlem. The 53-story building, to open June 15, will have 185 rental apartments set atop 20 floors of doctors’ offices.

Taller residential buildings make sense in a city like New York, of course. People are attracted to high-altitude residences because of the dramatic views they afford. For developers, the higher the building, the more square footage to sell or rent.

Marketing strategies have often turned on “highest” and “tallest” designations. When Donald J. Trump built Trump Tower at 721 Fifth Avenue in 1982, it was billed as the tallest “all-glass structure” in the city.

Today, at 664 feet, it appears as the city’s 52nd-tallest building over all.

Concern about Mr. Trump’s pride in such things apparently led Frank Gehry to make his New York rental tower a few feet lower than Trump World Tower. He told the developer, Bruce Ratner, to “make it a foot lower so we don’t have to deal with” Mr. Trump, The Observer quoted Mr. Gehry as saying in 2010 (to which Mr. Trump replied that he was “not a fan of much of” Mr. Gehry’s work, “although he is a darling”).

Lately, amid the hysteria for luxury apartments being fueled in large part by wealthy foreigners, something else has happened. While there has always been a premium for living on higher floors, developers are packing the biggest apartments in the top floors, giving them leverage to charge even more, said Jonathan J. Miller, the president of Miller Samuel, a real estate appraiser.

“The higher you go up, the higher the values go,” Mr. Miller said. “Not only are you incentivized to put more floors on the space than zoning permits, but there is a premium on those higher floors on a per-square-foot basis.”

But as with most issues in New York real estate, there are trade-offs. Height does give residents bragging rights, but you generally can’t have a terrace (or open your window at times) because of strong winds.

Most of New York’s tallest residential buildings are in Midtown. It’s an area that lends itself to tall structures because of its popularity with well-heeled foreign buyers who are less interested in neighborhoods than in park views and easy walks to theaters and luxury shopping, Mr. Miller said.

With so many developers claiming rights to superlatives about their buildings, I decided to investigate a bit more.

I started with the structure that is claiming the title of Tallest in the Upper East — 1214 Fifth. An official from Related Companies, its developer, gave me a tour. It was a gloomy day to see the building, which is just down the street from Mount Sinai Hospital, at 4 East 102nd Street. The lobby is unfinished, as are many other parts of the building. Workers in hard hats bustled about.

The apartments themselves are generously sized and boast impressive views of the northeast end of Central Park.

The residences have spacious entranceways, roomy closets and luxury finishes, including hidden dishwashers, stainless-steel appliances and marble bathrooms. “We were very specific in making sure that we appeal to that Upper East Side idea,” said Daria Salusbury, a senior vice president of Related.

Prices range from $5,500 to $6,500 a month (depending on how high up you are) for a 950-square-foot one-bedroom, to $9,000 for a 1,700-square-foot three-bedroom three-bath. A duplex penthouse with a 20-foot-high ceiling can be had for $10,500 a month.

Related is betting that the building, located amid a sea of co-ops on Fifth Avenue, can rise above the competition in the scorching-hot Manhattan rental market. Ms. Salusbury said she already had a “V.I.P. wait list” of people who have called to inquire about available rentals.

Yet for all its claims of regional superiority, 1214 Fifth, at 513 feet, will be the 183rd-tallest building in New York.

“It’s like an eagle soaring out here,” Ms. Salusbury said, while showing off the view from a 53rd-floor duplex penthouse. Staring at the softball fields, the bride-favorite conservatory and ant-sized bikers in the park, I couldn’t help but wonder: Are people more likely to get vertigo from the height itself, or from the price tag for these views?