BABYLON, NY – After more than a year of uncertainty and internal conflict, the leadership vacuum at Choose Chicago, the city’s powerful tourism and convention bureau, is finally nearing resolution. Kristen Reynolds, the current CEO of Discover Long Island, is expected to be named the next CEO of Choose Chicago — a position considered one of the most influential and highest-paid public roles in the city, with a salary of $520,000.
The move follows months of behind-the-scenes tension between allies of Mayor Brandon Johnson and members of the broader business and labor community over who should lead the agency. Johnson’s team had reportedly pushed for Deputy Mayor Kenya Merritt to take the post, but faced resistance due to her lack of experience in tourism and convention management.
Kristen Reynolds, formerly Kristen Jarnagin, a seasoned industry professional with nearly three decades in tourism leadership, is seen as a pragmatic pick to take on the city’s competitive hospitality landscape. Her resume includes senior roles with the Arizona Office of Tourism and Discover Long Island, a smaller agency by comparison but one that has gained national recognition under her leadership.
The delayed appointment comes at a critical moment for Choose Chicago, which has struggled with budget limitations while rival cities like Las Vegas and Orlando maintain significantly larger marketing and operations budgets. Choose Chicago’s current $33 million budget pales in comparison to Las Vegas’ $457 million, Visit Orlando’s $116 million, and Los Angeles’ $62 million, highlighting the urgency to scale up.
One of Reynolds’ key challenges will be advancing a proposed Tourism Improvement District that would raise hotel taxes to boost the agency’s funding — an initiative vital to maintaining Chicago’s competitiveness in hosting major events and conventions.
If finalized, Reynolds would replace interim CEO Rich Gamble, who stepped in following the January 2024 resignation of Lynn Osmond. Her appointment is expected to bring stability and much-needed industry experience back to the helm of Chicago’s tourism arm.
According to Long Island’s Newsday, Reynolds has confirmed her intention to depart Long Island after nearly a decade in her role, indicating that her potential appointment in Chicago would leave the top position at Discover Long Island vacant.
As of now, Discover Long Island has not announced a successor or interim leader to fill the impending vacancy. The organization has recently made internal promotions and new hires, reflecting its commitment to fostering talent and driving innovation in tourism. However, no official statements have been released regarding the appointment of a new CEO.
Reynolds’ departure marks a significant transition for Discover Long Island, as her leadership over the past decade has been instrumental in promoting the region’s tourism and economic development. The organization’s board will likely initiate a search process to identify a suitable successor to continue advancing Long Island’s prominence as a travel destination.
