On October 10, the streets of Chicago buzzed with a unique energy that transcended the typical autumn rhythm. Marking a milestone that few global metropolises can claim, the city celebrated ‘Best Big City Day,’ a tribute to its unprecedented 10-year streak as the ‘Best Big City’ in the annual Condé Nast Traveler Readers’ Choice Awards. This decade-long dominance, spanning from 2014 to 2023, has solidified Chicago’s reputation as a premier destination for culture, gastronomy, and architectural marvels. To commemorate this ‘Perfect 10,’ the organization Choose Chicago orchestrated a series of high-profile activations that brought the city’s spirit to the water and the dinner table.
The Anatomy of a Decade-Long Reign
The Condé Nast Traveler Readers’ Choice Awards are widely considered the gold standard in travel, relying on tens of thousands of consumer votes rather than editorial selection alone. To hold the top spot for ten consecutive years requires not just world-class amenities, but consistent execution across hospitality, dining, and infrastructure. Unlike other cities that might rely on a single landmark or season, Chicago’s appeal is structurally diverse. From the world-renowned Art Institute of Chicago to the vibrant, revitalized Chicago Riverwalk, the city offers an urban experience that seamlessly blends Midwestern hospitality with a sophisticated, global cosmopolitan edge.
Industry analysts attribute this stability to Chicago’s ability to evolve. Throughout the last ten years, the city has successfully integrated new, sustainable urban design projects while aggressively promoting its deep-rooted cultural institutions. The consistency in winning suggests that tourists are not just visiting once; they are returning, which is the most critical metric for any global travel destination.
Commemorating 10/10: A City-Wide Activation
The ‘Best Big City Day’ on October 10 was more than just a celebratory title; it was an experiential campaign designed to reward the residents and visitors who fueled the city’s success. Choose Chicago turned the downtown core into a festival of civic pride. The centerpiece of the celebration occurred on the Chicago Riverwalk, where a floating house party served as a testament to the city’s relationship with its waterways—a transformation from industrial shipping artery to a prime recreational destination.
This activation wasn’t merely about visibility; it was about partnership. Two of Chicago’s most iconic brands stepped up to mark the occasion. Goose Island Beer Co., the city’s pioneering craft brewery, developed a limited-edition ‘Perfect 10’ beer. The brew was not just a promotional gimmick but a nod to the city’s deep roots in the craft beer revolution, creating a tangible connection between the city’s history and its current stature. Simultaneously, Eli’s Cheesecake—a staple of Chicago culinary identity—distributed commemorative cheesecakes, underscoring the city’s ‘comfort meets class’ food culture.
The ‘Perfect 10’ Effect: Economic and Cultural Impact
Beyond the celebratory atmosphere, the ‘Perfect 10’ holds significant economic weight. In the travel industry, awards act as massive ‘trust signals.’ When potential travelers research a destination, a decade-long streak of top-tier recognition lowers the friction of the decision-making process. For the tourism sector, this is invaluable. The ripple effects of this recognition are felt across the board—from luxury hotel occupancy rates to the vitality of the local restaurant scene, which has seen an explosion of Michelin-starred establishments in recent years.
Furthermore, the 10-year streak impacts the city’s ‘brand equity.’ Chicago is no longer fighting to prove it belongs among the world’s elite cities; it is now working to define what that elite status looks like. The ‘Best Big City’ label assists Choose Chicago in high-stakes negotiations for conventions, large-scale sporting events, and international tourism partnerships. It is a powerful narrative tool that frames the city not as a ‘hidden gem,’ but as a dominant, reliable, and essential stop on the global itinerary.
Looking Toward the Second Decade
As the city pivots from celebrating the last ten years to planning the next, the conversation among urban planners and tourism officials has shifted toward sustainability and accessibility. The ‘Best Big City’ title is not static; it is subject to the changing demands of travelers. Future strategies, already being whispered in the corridors of Chicago’s civic leadership, likely involve enhancing the tech-integrated tourist experience and expanding tourism footprint beyond the downtown ‘Loop’ into the city’s diverse and vibrant neighborhoods. The success of the 10/10 celebration proves that Chicago understands the power of ‘placemaking’—the ability to turn a city into a narrative that visitors want to be a part of. As the city looks forward, the challenge will be to maintain this momentum, ensuring that the next ten years are defined by the same level of innovation and civic engagement that defined the last decade.
FAQ: People Also Ask
How does the ‘Best Big City’ selection process work?
Condé Nast Traveler’s Readers’ Choice Awards are determined by annual surveys completed by thousands of readers. It is a data-driven process based on visitor sentiment, satisfaction, and the quality of experiences across hospitality, dining, and activities.
Why was October 10 chosen for the celebration?
October 10 (10/10) was selected as a symbolic date to represent Chicago’s 10th consecutive win as the ‘Best Big City’ in the Condé Nast Traveler awards.
What organizations were involved in the 10/10 event?
Choose Chicago, the city’s primary tourism organization, led the effort. Key brand partners included Goose Island Beer Co., which provided a signature beer, and Eli’s Cheesecake, which provided commemorative treats.
Is the ‘Best Big City’ award just about the downtown area?
While downtown iconic spots are major draws, the award reflects the overall city experience, including its neighborhood culture, culinary landscape, museums, and public infrastructure, which Choose Chicago promotes as an interconnected ecosystem.


