Just as his political party affiliation has changed over time, President Trump’s words describing the city of Chicago have shifted as well.
In 2004, during a visit to watch the demolition of the old Chicago Sun-Times building, he described Chicago as “a great city.” His Trump Tower and Hotel would eventually be built at that riverfront location.
In 2008, Trump and his children visited Chicago again to place their hands in cement to celebrate the completion of the luxury high-rise.
Now, in 2025 he sometimes calls Chicago a great city, but then qualifies that description with a more negative tone. On September 19, as he signed Executive Orders in the Oval Office, he said “They’re losing 4, 5, 6 people a week getting killed by bullets, by knives.” And, on October 15 during a press conference with FBI Director Kash Patel, he said “They had in a short period of time, 4,000 murders in Chicago.”
“Chicago’s always had a challenge with our reputation nationally … but right now that’s amplified,” said Choose Chicago’s President and CEO Kristen Reynolds.
Impact of words
Choose Chicago is a nonprofit organization tasked with marketing Chicago.
“Chicago is vibrant. It’s diverse. It’s exciting. It’s cultural. It’s walkable,” Reynolds said.
Her job is to bring business leaders, convention goers and tourists from around the country and the world to the city.
Over the summer of 2025, the President’s words, along with images of ICE and other federal agents patrolling city streets holding guns and detaining illegal immigrants, has not yet had an impact on visitors.
Choose Chicago reports hotel bookings were 4.3% higher than the summer of 2024.
Reynolds said this is what she hears from first-time visitors, “People have a mindset and then they come here and they go, ‘Wow, the city is beautiful. It’s amazing. It’s clean. I love it. I had no idea.'”
Reynolds fights back on the picture the President paints of a crime-ridden and unsafe city.
“When you layer on this negative narrative about our city, which is incredibly false and doesn’t represent who we are, it creates an entire new layer of challenge that’s really difficult for our team.,” she said.
Scott Wilson / CBS News Chicago
On September 2, President Trump said this, “Chicago is a hellhole right now. “
Choose Chicago used the reaction to that statement in a brief campaign by reposting social media videos from content creators who added the hashtag, #ShowMeYourHellhole.
“We wanted to give a voice to the people, to our residents and visitors that know and love Chicago that are here in real time. So giving a voice to the people and allowing people to create content, share their message, share what they love about our city. And that’s the only way we can combat it.”
Reynolds is hoping that the ground roots social media campaign along with a new, more formal effort called “Never Done, Never Outdone” will help protect the $20 billion in revenue and 130,000 jobs tourism generates annually for Chicago.
“When people aren’t choosing Chicago, regardless of your political views, that hurts small business, that hurts our restaurants, that hurts our employees who rely on this industry.”
Choose Chicago also puts out an annual visitors guide. This year, Chicago’s Trump Hotel had a full-page advertisement touting, among other things, the city’s culture, museums and sandy beaches.
“Clearly he sees the benefit of Chicago enough to build a beautiful hotel here. So, he understands that our city has a lot to offer,” Reynolds said.
Violent crime comparison
CBS News Chicago analyzed violent crime statistics from 2004 and 2008, the years Trump visited Chicago to mark the start and completion of his hotel and condo building project, and compared those numbers to 2025 through the first eight months of each year.
Violent crimes analyzed include robbery, aggravated battery, aggravated assault, homicide and criminal sexual assault.
More violent crimes of every type happened in 2004 when Trump had only good things to say about Chicago. Overall, violent crime was 65% higher that year, according to our analysis of Chicago Police Department data.
Four years later, when the Trump Tower was finally finished, again more violent crime was happening then compared to now. One exception: criminal sexual assault, which is 4% higher in 2025 than in 2008, according to our analysis.
“People really don’t know what to believe and don’t understand what’s really happening on the ground here,” Choose Chicago’s president said.
Despite the positive news about less violent crime overall in 2025 and the fact that Chicago recently received Condé Nast’s Best Big City in the U.S. designation for the ninth straight year, Reynolds is concerned about the perception people have of the city because of what the President has been saying lately.
“I worry about conventions and meetings that want to book Chicago. We’re booking now for 2040 for meetings and conventions. So, what is happening now is impacting our city for decades to come,” Reynolds said.
