It surpassed the city's John Hancock Center as the building with the highest residence (apartment or condo) in the world, and briefly held this title until the completion of the Burj Khalifa.

[6] The building has 2.6 million square feet (240,000 m2) of floor space, rises to 98 stories, and houses 486 luxury residential condominiums.

"[15] However, in 2011, the award-winning plantings of small sumac trees, ferns and native grasses with yellow, orange and red hues were removed and replaced with evergreens like junipers and boxwoods, pieces of gray stone, and purple perennials (catmint and salvia), which may require less watering.

[16] The building broke the record for the world's highest residence above ground level, held since 1969 by the nearby John Hancock Center.

[18] The Trump International Hotel and Tower rises 1,400 feet (426.7 m) from the building's main entrance on Wabash Avenue to the tip of the architectural spire.

[25] A Chicago-based design firm planned to create and float four giant pig balloons in front of the sign as a protest,[35][36] but were unsuccessful getting US Coast Guard and Chicago Department of Transportation approvals.

[60] The Terrace, which opened on June 25, 2009,[58] has views of the Chicago River and Lake Michigan as well as Navy Pier's seasonal Wednesday and Saturday evening fireworks, and was designed for outdoor or "al fresco" dining.

[69] The spa offers gemstone-infused (diamond, ruby, or sapphire) oil massages, hydrating masques, exfoliating salts and the "Deluge shower".

On October 16, 2004, Donald Trump and Hollinger International, the parent company of the Chicago Sun-Times, completed the $73 million sale of the former home of the newspaper a week after it relocated.

[96][97][98] The demolition and construction were financed by a $650 million loan from Deutsche Bank and a trio of hedge funds, one of which George Soros backed.

[11] In July 2005, water from the river began seeping into the building site, through crevices in a corner where the foundation wall meets the Wabash Avenue Bridge.

[101] In October 2006, controversy erupted over a 10-by-4.5-foot (3.0 by 1.4 m) street kiosk at the foot of the Magnificent Mile in front of the Wrigley Building at 410 North Michigan Avenue that advertised Trump Tower a full block away.

[107] In January 2007, Trump cited both a clause about "matters beyond [the] seller's reasonable control" and the desire to "have more income to handle potentially higher construction costs".

[111] In September 2008, due to slow unit sales, Trump sought to extend both loans until mid-2009 because he felt that it was necessary in the business environment and expected from the outset of the contract.

[113] Trump filed suit later that month against Deutsche Bank in New York State Supreme Court in an effort to excuse a repayment of more than $330 million that had been due November 7, and to extend the construction loan for an unspecified period of time because of extenuating circumstances during the 2007–2008 financial crisis.

[121] During 2005, Donald Trump Jr., who had been involved in the building since its earliest stages in 1999, was overseeing the construction with weekly visits, while Rancic worked on sales and marketing.

[127][128] Bovis Lend Lease, noted for work on Disneyland Paris, the Petronas Towers, and the Deutsche Bank Center, was the construction company.

At the completion of construction the building was the tallest formwork structure in the world,[17] and follows in the footsteps of its neighbor, Marina City, as well as Chicago's Two Prudential Plaza, as past recordholders.

[101] Two earlier business decisions by the Chicago Sun-Times led to substantial savings of time and money during the Trump Tower's construction.

The original 1950s sea wall was built by the newspaper company to bomb-shelter thickness, to withstand a Cold War attack, and thus did not have to be broken down and rebuilt.

To celebrate the milestone, a yellow tower crane raised a bucket full of concrete and an American flag to the rooftop of the skyscraper.

[80] At the September 2008 topping off ceremony, Donald Trump marketed his hotel by expressing doubts about the Chicago Spire ever being completed due to the Great Recession.

[139][140] Trump's hotel was 25% unsold at the time of the 2008 topping off ceremony, and was expected to need the mid-2009 construction loan extension that has caused legal complications.

[159] In August 2018, Illinois Attorney General Lisa Madigan filed suit in the Circuit Court of Cook County alleging that though Trump Tower's National Pollutant Discharge Elimination System permit expired on August 31, 2017, it continued to release almost 20 million US gallons (76,000 cubic metres) of water it uses for cooling into the river each day.

[161] Madigan's successor Kwame Raoul sued the Trump Organization again in September 2023, alleging the tower continued to take in river water without a valid permit.

[163] On Sunday, October 18, 2020, at around 5:30 PM (CDT), an unidentified man in his 20s suspended himself from a landing located on the 16th floor and hung down the side of the skyscraper facing the Chicago River for more than thirteen hours.

He then demanded to speak to U.S. President Donald Trump and acknowledged the hard work of the Mayor Lori Lightfoot and Chicago emergency services during the COVID-19 pandemic.

[167][168][169] In 2024, The New York Times and ProPublica reported that the Internal Revenue Service investigated whether Trump had twice written off losses through construction cost overruns, lagging sales, and selling residential units below value.

[170][171] The final confrontation between Batman and the Joker in the film The Dark Knight was shot in the Summer of 2007 at the very top of the construction site of the then partially completed tower.

[176][177] The building, as well as its address "N Michigan Av / E Wacker Dr", feature prominently in the opening of the TV series The Crazy Ones, created by David E. Kelley and aired by CBS during the 2013–2014 season.