TSNN Exclusive: Q&A with Choose Chicago’s New President & CEO Kristen Reynolds

After searching for more than one year for a permanent replacement, Choose Chicago has tapped Kristen Reynolds, who has served as Discover Long Island President and CEO since 2015, as its new president and Chief Executive Officer, effective May 5. She will lead Chicago’s convention and tourism industry, which is a key driver of the city’s economy, generating $19.5 billion in leisure and business spending in 2023, according to the latest research by Choose Chicago. 

The position has been vacant since Lynn Osmond stepped down on January 31, 2024. Choose Chicago Board Member Rich Gamble, who served as interim CEO during the search, will support Reynolds in her onboarding. 

Context: Reynolds brings 27 years of experience in destination marketing, strategic partnerships, and tourism advocacy. Under her leadership at Discover Long Island, she increased tourism revenue, spearheaded new initiatives for leisure and business markets, and strengthened regional economic development, according to a press release. Reynolds also worked for the Arizona Lodging & Tourism Association, the Sheraton Wild Horse Pass Resort & Spa, and the Arizona Office of Tourism. 

Backstory: A Certified Destination Management Executive (CDME), she also serves on the Board of Directors for Destinations International and the New York State Hospitality & Tourism Association, and previously was president of the New York State Destination Marketing Organizations. Reynolds earned a bachelor’s degree in journalism from Arizona State University. 

What they’re saying: “Kristen Reynolds is a proven leader in the tourism industry and we welcome her to Chicago,” said Chicago Mayor Brandon Johnson. “With major global events on the horizon and our city continuing to break tourism records, Kristen’s leadership will be instrumental in strengthening Chicago’s position as a top destination for visitors, conventions, and business investment.” 

Big picture: “Illinois is in the middle of everything and offers some of the most diverse and engaging opportunities anywhere in the country,” said Illinois Governor JB Pritzker. “I look forward to working with Kristen and Choose Chicago on spreading that message, encouraging people to visit Chicago, and showing businesses why we’re the best place in the country to operate.” 

Looking ahead: Reynolds steps into the role at a pivotal time as Chicago builds on record-breaking convention and tourism momentum heading into the spring and summer months. In 2024, the Democratic National Convention generated $371.4 million in economic impact while the NASCAR Chicago Street Race weekend generated an estimated $128.1 million in economic impact for the city. 

What does her appointment mean for the exhibition industry? We caught up with Reynolds to get her initial thoughts on the new role. Plus, we wanted to get to know the female leader who will be running one leading of the country’s busiest trade show cities. 

TSNN Q&A with Reynolds  

Tormohlen: You’re stepping into this role at a moment of incredible momentum for Chicago’s tourism and trade show sector. What are your top priorities in your first 100 days, especially when it comes to meetings and conventions?   

Reynolds: Chicago has long been a leader in the meetings and conventions space, and I’m thrilled to join this team at such an exciting time.  Early on, my top priorities will be to support the incredible Choose Chicago team and build relationships with local leaders in the hospitality industry, the corporate sector, and at McCormick Place, as well as with the clients that are key to our continued growth in the meetings sector. With IPW 2025 and the Destinations International Annual Convention coming soon, I am looking forward to the opportunity to position our city as a best-in-class global destination for years to come.    

Tormohlen: Chicago has long been a cornerstone of the U.S. trade show market. How do you see Choose Chicago evolving to meet the changing needs of large-scale event organizers and exhibitors?   

Reynolds: I firmly believe Chicago is the best trade show city in the U.S., and I am excited to work with our customers to understand their needs. In fact, this week I am in Washington DC with the Choose Chicago team for the PCMA Business Events Industry Week, meeting with dozens of our current and prospective clients. To keep our status as the best trade show city, we need a bold vision and the resources to execute it. I look forward to working with the Choose Chicago team and partners to find new sources of funding and give our team the necessary resources to compete on a larger scale and invest in attracting major conferences and events while delivering world-class leisure marketing campaigns.  

Tormohlen: You’ve led transformational growth in Long Island and held key leadership roles across the industry. What lessons from your previous work are you most excited to bring to Chicago’s meetings and events scene?   

Reynolds: While on the surface Chicago and Long Island may seem very different, there are lots of complex similarities and opportunities. I am excited to bring the lessons I have learned and the skills I have developed in my career to this new challenge. I have built a career in the DMO space and, as a Certified Destination Management Executive, I understand what it takes to lead organizations of all sizes and outlooks. While Chicago is complex, our team will not be satisfied with the status quo. We will work tirelessly to strengthen Chicago’s reputation, grow the visitor economy, and ensure long-term success for the tourism sector.  

Tormohlen: On a personal note—what was your first impression of Chicago, either from a past visit or this recent transition? Any favorite neighborhoods or spots you’re excited to explore?   

Reynolds: My husband is actually from the Chicago area and one of our daughters is attending college there, so it already feels like we are coming home. Chicago’s 77 neighborhoods are one of our distinguishing factors, so I can’t wait to explore them. We’ve decided to rent in the short-term, so we have the opportunity to really explore before committing to one neighborhood. And of course, Chicago is a great food town! Someone has already asked me if I was Team Hotdog or Team Deep Dish Pizza, and I said that I can’t wait for a great Chicago steak!  

Tormohlen: Leadership in this industry requires equal parts strategy and heart. Who or what inspires your leadership style as you take on this next chapter?  

Reynolds: At my core, I am a collaborator. From my time lobbying in Arizona to working with more than 100 towns, villages, and hamlets in Long Island, I know that to accomplish big goals, you must bring people together. As I prepare to take on this role in Chicago, it will be critical to ensure that as an organization we continue to lead with a collaborative and inclusive approach. 

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