The winning streak is the first in the award's 30-year history.
The magazine cited Navy Pier, McCormick Place, theaters and sporting arenas for attracting visitors. Over 750,000 readers voted. They were asked about their previous experiences in Chicago, rating the city's culture, attractions, hospitality and more.
That's no surprise to Colorado native Dylan Bell.
"I have wanted to come to Chicago for many years, and it's very beautiful, especially this part of town," he said.
Choose Chicago reports people booked 3.56 million hotel rooms from June through August of this year, generating $949 million in revenue. Both are record numbers.
All that was driven by major events, including Lollapalooza, the downtown NASCAR race and numerous large-scale concerts at Soldier Field this summer, as well as a host of conventions.
Choose Chicago says tourism is a major economic driver for Chicagoland's economy, generating over $20 billion economic impact, over 55 million visitors and over 130,000 jobs in the Chicago area every year.
"We saw more tourists filling hotel rooms in Chicago than ever before. Over 3.5 million hotel rooms filled. That is a record up over 4% over last year and surpassing our pre-pandemic record in 2019," said Stephen Crano, with Choose Chicago.
It comes as the Department of Homeland Security continues to ramp up its immigration enforcement efforts.
President Donald Trump has repeatedly bashed Chicago as being an unsafe city despite crime numbers being on the decline.
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It's a concern for one woman who is in town from Nashville with her three children for fall break.
"We're just gonna be doing to and from. Other than that, we're not venturing out. We're gonna stick to safe to us," tourist Natalie Murchie said.
Other tourists in town say it's the city's diversity and other offerings that made them want to visit.
"We haven't experienced anything unusual. It's the same thing when I came here 10 years ago as it is today. I don't see any difference," tourist Veronica Lister said.
"It really hasn't affected us. We just want to come out here for a birthday weekend and enjoy some festivities," tourist Kevin Drake said.
San Francisco, California was this year's runner-up, and Milwaukee, Wisconsin came in third.
Those who love the city of Chicago say they hope that all the qualities that make the city shine continue to do so, maybe enough to garner the award for the 10th year.