For the 10th consecutive year, Chicago has been named the “Best Big City” in the United States by Condé Nast Traveler in the magazine’s annual Readers’ Choice Awards.[1] That makes it the first and only city to hold the title for a decade in a row since the travel magazine debuted the award in 1988.[2]
New York City, the usual rival in this conversation, didn’t come close to the top spot this time. Here’s what the 2026 results show, how the vote works, and what the numbers behind Chicago’s tourism economy say about the streak.
A Decade of Winning
Chicago first earned the title in 2017 and has held onto the top ranking ever since.[3] The 2026 results were announced on a Tuesday in early October. Mayor Brandon Johnson called the milestone a testament to everything Chicago has to offer, one the whole city can celebrate with pride.[2]
A streak this long is unusual for any annual ranking. When Chicago took its ninth title in 2025, Time Out described it as the longest winning streak in the awards program’s history of more than 30 years.[4] The tenth win extends that record.
How the Readers’ Choice Vote Works
The award isn’t decided by a panel of critics or a statistical formula. Nearly 800,000 readers submitted survey responses for this year’s Readers’ Choice Awards.[1] The city awards are broken into top 10 lists for small and big destinations in the country.[2]
That reader-driven format matters when you read the result. It reflects what travelers who follow the magazine enjoyed and recommended, not an objective measure of livability or safety. Still, a result that repeats for ten years suggests the city’s appeal isn’t a one-season fluke.
Where New York City Landed
In 2026, New York was named the fourth-best big city in the U.S. by readers, just behind Boston at No. 3, San Francisco at No. 2 and Chicago at No. 1.[5] That’s a respectable finish, though well short of the top. New York has also moved around in recent years.
In 2025, New York City didn’t crack the top five among big cities[6], and it was listed at No. 9[6]. Back in 2021, New York was the runner-up to Chicago[7]. So the city has finished anywhere from second to ninth in the years covered here, with Chicago ahead every time.
What Condé Nast Says Makes Chicago Special
The magazine’s write-up has stayed fairly consistent over the years. Condé Nast Traveler’s website praises the city’s impressive architecture, first-rate museums, brilliant chefs and massive brewing scene.[2] The editors also suggest that it takes several repeat visits to get through a list of must-dos[2].
Local tourism officials point to a broader mix. According to the travel site, the city draws visitors with architecture, vibrant neighborhoods, major events, cultural institutions, world-class food, genuine hospitality and ongoing growth.[1] Choose Chicago’s anniversary page also notes that the city has welcomed major sporting events like the NFL Draft and the world’s first NASCAR Street Race[8].
The Tourism Numbers Behind the Title
The award comes with real economic weight. The city welcomed 56.8 million visitors this past year, generating a record $21.5 billion in visitor spending and supporting 135,360 local jobs across the region.[1] Those figures cover 2025, the year before this latest win.
Hotels also had a strong run. According to Choose Chicago, the city added more than 2,100 tourism-related jobs in 2025 and set annual records for leisure hotel room demand, hotel revenue, average daily rate, revenue per available room and hotel tax collections.[1] It’s worth remembering that the tourism agency supplied these numbers, so they come from the people promoting the city.
The Rest of the 2026 Top 10
The big city list has a few surprises beyond the top spot. After Chicago come San Francisco, Boston, New York City and Milwaukee.[3] Oakland, Portland, Nashville, New Orleans and San Diego round out the list.[3]
Milwaukee keeps showing up near the top. It ranked third in 2025, according to Time Out’s rundown of that year’s list[6], and fifth this year. On the small city side, Charleston, South Carolina was named the best small city[5].
Best Big City Day and the Victory Lap
Chicago doesn’t let a milestone pass quietly. The city proclaimed Saturday, October 10, “Best Big City Day,” inviting Chicagoans and visitors to get out and experience the city.[9] Choose Chicago marked the occasion with its “A Perfect 10” campaign, along with special events, social media activations and local collaborations.[9]
The plans included some local flavor. Promotions included a special beer and festivities on the Riverwalk.[2] Choose Chicago also scheduled a set from House music pioneer DJ Lori Branch aboard a boat near City Winery.[2]
What the Streak Does and Doesn’t Prove
A tenth straight title is a strong signal of traveler goodwill. Choose Chicago’s president and CEO, Kristen Reynolds, credited the city’s hospitality and its “Midwestern Nice.”[10] Readers keep picking the city, and the visitor figures suggest they keep showing up too.
It’s still one reader survey, and it measures impressions, not every part of city life. New York’s fourth place doesn’t make it a lesser destination, since the two cities simply appeal to travelers in different ways. What the streak does show is that, for ten straight years, a very large pool of travelers has decided Chicago is the American big city worth the trip.
