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This Just In

Never Done, Never Outdone: Inside Choose Chicago President & CEO Kristen Reynolds’ First Year

ANDREW WARRICK, SENIOR DIGITAL EDITOR
KR headshot

CHICAGO — Choose Chicago President & CEO Kristen Reynolds, CDME, recently hit her one-year mark in this vital role, in which she helps bring trade shows and events to one of the world’s top destinations.  

Trade Show Executive (TSE) sat down with Reynolds to talk about her achievements, how she is helping Choose Chicago weather economic and political headwinds, and her vision for its future.  

ANDREW: Could you walk through how your first year went? 

KRISTEN: My first year at Choose Chicago has been a whirlwind — in the best possible way. It’s been a year defined by momentum, record-breaking growth and laying the foundation to ensure Choose Chicago not only succeeds, but leads. 

Chicago outperformed national hotel demand trends in 2025, with 11.9 million room nights booked, representing a 2.3% year-over-year increase and generating a record $2.9 billion in hotel revenue.  

Those results were driven by strong collaboration across the city, particularly with our partners at McCormick Place, the hospitality community, cultural institutions, labor leaders and local businesses. 

What has been most rewarding for me personally has been becoming part of the Chicago community and having the opportunity to represent one of the world’s truly iconic cities. 

Getting to know our Customer Advisory Board, our clients and our partners — who trust us with their business while also challenging us to continually improve — has been an incredible learning experience and one of the highlights of this first year. 

ANDREW: What were some highlights and/or achievements?

Photo Courtesy of Choose Chicago

KRISTEN: There were many memorable moments this year.  

Chicago proudly hosted IPW and Destinations International’s Annual Convention, both of which showcased our city on a global stage and reinforced Chicago’s reputation as a premier meetings and tourism destination. 

We also launched our new “Never Done, Never Outdone” marketing campaign, alongside our “All for the Love of Chicago” social media initiative and podcast, all designed to authentically tell Chicago’s story through the voices of the people who love this city most. 

Personally, I had the honor of speaking at the James Beard Awards, throwing out the first pitch at a Cubs game, and experiencing countless bucket-list moments that reminded me just how special Chicago truly is. 

But without question, the most transformational achievement during my first year was the passage of the Chicago Tourism Improvement District (TID). The TID creates a new private funding mechanism that will allow Chicago to compete on a far more level playing field with other major destinations across the country.  

It represents a generational investment in Chicago’s visitor economy and will be instrumental in driving future meetings, conventions, international visitation and long-term economic growth. 

ANDREW: Did you encounter any challenges? If so, how did you work through them? 

KRISTEN: The global travel industry continues to face economic and political headwinds, and every destination is competing hard for meetings, conventions and large-scale events. We are staying disciplined, collaborative and focused on Chicago’s strengths.  

We have world-class convention infrastructure led by McCormick Place, strong hotel inventory, outstanding air access and a visitor experience that is hard to replicate.  

We are also being very intentional about how we position Chicago, because in a competitive environment, you have to remind planners and attendees not just that the city can host major events, but that it can host them exceptionally well.  

For example, McCormick Place hosted the Adidas Windy City National Qualifier at the beginning of April — and it pulled in 20,000 visitors.  

Nutanix’s .NEXT event saw more than 5,000, the American Academy of Neurology had about 13,000 — and as of this interview, we’ve got the NBA Draft CombineCLOC and all these other great events going on.  

And that’s just from a convention perspective. We’ll be hosting hundreds of thousands of visitors this spring and summer for events like the opening of the new Obama Presidential Center, James Beard Awards, Chicago Jazz FestivalWNBA All Star GameLollapalooza and much more.  

So, there are challenges, yes, but there are also so many success stories. 

ANDREW: How do you think Choose Chicago has changed in the past year? 

KRISTEN: I think both Choose Chicago and the city itself have really come into their own over the past year. There is a renewed confidence, energy and sense of pride that you can feel throughout our organization and across the broader tourism and hospitality community. 

Our “Never Done, Never Outdone” campaign and our “All for the Love of Chicago” initiatives have helped reintroduce Chicago to the world in a more authentic, bold and emotional way.  

We’re telling our story with confidence again — and people are noticing. There’s a new buzz surrounding Chicago that extends far beyond visitors and meeting attendees.  

Our residents, partners, hospitality workers and business community are rallying around the city in a way that feels incredibly energizing and unified. 

Internally, Choose Chicago has become more focused, collaborative and driven by impact. There’s a stronger sense of urgency around growth, innovation and ensuring we remain competitive on a global stage.  

At the same time, we’ve strengthened relationships across the city and built greater alignment around a shared vision for Chicago’s future. 

That momentum is translating into real results — from record hotel performance and convention bookings to increased enthusiasm from meeting planners, travel buyers and international media. 

Chicago is getting its swagger back, and I think the industry can feel it. 

ANDREW: Were there any trade shows or events that you want to spotlight from your work so far?

The National Restaurant Association Show was recently held at McCormick Place.

KRISTEN: One of the things that excites me most is the overall strength and variety of Chicago’s events calendar at McCormick Place this year.  

In 2026, that includes major gatherings like The Inspired Home Show, the National Restaurant Association Show, the American Society of Clinical Oncology (ASCO) Annual MeetingIMTSPACK EXPO and the Radiological Society of North America (RSNA).  

In addition to this wide range of trade meetings, we also have a packed schedule of sporting events, festivals and concerts. That diversity is a real advantage for the city.  

More broadly, our ability to deliver 65 citywide conventions shows that Chicago continues to be a place where major events can succeed. It speaks to the strength of our venues, our hotels, our transportation network and our hospitality community, all working together to deliver a high-quality experience. 

I can’t pick just one, but how could you not love all of the colorful costumes at C2E2? Those fans go all out. 

ANDREW: What is your vision for Choose Chicago’s future?

KRISTEN: My vision for Choose Chicago is not simply to maintain momentum, but to help position Chicago as the most dynamic, forward-thinking and sought-after meetings and events destination in the world. 

Chicago has always had the infrastructure, the accessibility, the hospitality expertise and the cultural assets to compete with anyone. What excites me now is that we also have the momentum, alignment and confidence to fully step into that leadership role. 

Our future is about more than increasing visitation numbers — it’s about creating lasting economic impact for our city and ensuring that tourism and meetings continue to support jobs, businesses, neighborhoods and opportunities across Chicago.  

It’s about attracting the conventions, trade shows, corporate meetings and global events that shape industries and bring people together in meaningful ways. 

We want meeting planners and attendees to think of Chicago not just as a great option, but as the destination that consistently delivers at the highest level — a city that combines unmatched convention infrastructure with authenticity, creativity, culture and unforgettable experiences. 

I believe Chicago’s best chapter is still being written. 

ANDREW: What is on your radar at the moment?

Chicago Passes Paid Leave Measure That Will Impact Trade Show Attendees
Photo Credit: MPEA

KRISTEN: Right now, I am focused on how we convert strong performance into long-term market share, including in the meetings and conventions space.  

We have real momentum, but this is a highly competitive environment, so we are looking closely at future booking opportunities, client engagement, international sentiment and how we continue to support major events.  

I am also focused on making sure we keep building a compelling case for Chicago as a destination that delivers both business results and a standout visitor experience.  

ANDREW: Is there anything else you would like to add? 

KRISTEN: Chicago is having a moment. 

Our conventions are breaking attendance records, exhibit halls are selling out and meeting planners continue returning year after year because Chicago knows how to host at the highest level. 

The data certainly shows progress, but just as important is the confidence and optimism we are seeing across the city.  

Our job at Choose Chicago is to continue building demand, supporting our partners and ensuring visitors from around the world understand that Chicago remains one of the greatest places anywhere to bring people together. 

Most importantly, I want Choose Chicago to continue serving as a unifying force for this city. When tourism succeeds, Chicago succeeds.  

Our visitor economy creates jobs, drives investment, supports small businesses and showcases the very best of who we are to the world. 

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