Seven-Year Sweep
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We do a lot of hand-wringing here in the Windy City about the many problems we face and how intractable they can often appear to be. But occasionally we get a reminder that all is not doom and gloom on the southwest coast of Lake Michigan.
One of those regular reminders has been Condé Nast Traveler‘s Readers’ Choice Awards which just named Chicago the Best Big City in the United States for the seventh year in a row! Not bad for a place certain right-leaning politicians love to hate and that regularly gets portrayed as a living hell-hole where you can’t walk out your front door without being accosted or shot!
Condé Nast Traveler‘s Readers’ Choice Awards just named Chicago the Best Big City in the United States for the seventh year in a row!
The magazine does its survey annually and gets input from about 520,000 people. Chicago’s seven-year consecutive winning streak shows that the city’s popularity is enduring and has been able to weather a lot of challenges, including a pandemic, the civil unrest following the death of George Floyd, and the near constant bashing by politicians with a strong dislike of Sanctuary Cities with Democratic mayors.
Editors from the magazine call Chicago a “world-class destination” with “impressive architecture, first-rate museums, brilliant chefs, and massive brewing scene.” In an acknowledgement of the depth and breadth of the city’s resources and attractions, the magazine states “it’ll take several repeat visits to get through your list of must-dos.”

For people in the housing business, it is especially easy to lose sight of all that Chicago offers. As housing providers, we seem to be constantly on the defensive over repeated attempts by city and county officials to make it harder to run our businesses and maintain control over our properties. Combined with stagnant population growth, soaring costs (including real estate taxes, insurance rates and utility bills) and the challenges of maintaining an aging building stock, it is easy to see how we can internalize this “sky is falling” mentality.
But, to the millions of people who visit Chicago each year, there is another side to the story. Chicago remains one of the most vibrant and exciting urban centers, not just in the United States, but really anywhere on earth. Our Lakefront has no real parallel in the country and few globally (note to New York – when we look across the water in Chicago, we see infinity, not New Jersey, Brooklyn or Queens… just sayin’).
Chicago’s seven-year consecutive winning streak shows that the city’s popularity is enduring and has been able to weather a lot of challenges.
And people keep voting with their feet. According to Choose Chicago, a private, non-profit organization that promotes Chicago as a tourist and convention destination, approximately 50 million people visited the city in 2023.
While none of this is going to solve the problems we are left with after the “best city” bragging rights wear off, it is still a good reminder that we live in an extraordinary place that many other people very much want to experience for themselves. Despite all the political headwinds and the negative press we are subject to on a nearly daily basis, people from outside Chicago just keep on coming to experience the city for themselves. And they certainly seem to like what they see, at least enough to keep voting Chicago their number one choice, now for seven years running! That’s something to feel good about.