Choose Chicago names new CEO to lead city's tourism agency
After a yearlong search, Chicago has chosen a New York destination marketing executive to lead the city's tourism efforts.
Kristen Reynolds, 51, who has been president and CEO of Discover Long Island for nearly a decade, will head west to take the same role at Choose Chicago, the agency tasked with promoting the city as a travel destination.
Moving on from a successful run on Long Island, an expansive and populous region stretching from the outer boroughs of New York City to seaside resort communities like the Hamptons, Reynolds is ready for the challenge and opportunity of building back Chicago's tourism numbers in the post-pandemic landscape.
'I'm all about breaking records and exceeding expectations, and I want to do the same thing here in Chicago,' she said Thursday. 'I want to make sure that we continue to grow not only the convention side, but the leisure side.'
Choose Chicago has been without a permanent CEO since Lynn Osmond stepped down at the end of January 2024. Board member and former Chicago Tribune executive Rich Gamble has served as interim CEO during the extended search for Osmond's successor.
The city, which had 61 million visitors in 2019, is slowly clawing back to pre-pandemic levels, reaching nearly 52 million visitors in 2023, according to Choose Chicago. International tourism accounted for about 1.8 million visitors in 2023.
Choose Chicago expects to release 2024 visitation numbers in June, but the city has been gaining momentum, catalyzed by major events such as the Democratic National Convention in August, which along with recurring tentpole events such as the NASCAR Chicago Street Race and Lollapalooza helped boost summer hotel stays 5% last year compared with 2023.
The busy schedule last year may also have delayed the search for a new Choose Chicago CEO.
'With all that we had going on last year, we had some pretty monumental events … we knew going into the search that we could take our time, because we had a qualified leader in the interim,' said Glenn Eden, Choose Chicago's board chair.
Eden said there were a lot of stakeholders in the process that led to hiring Reynolds, who starts May 5. She was the consensus choice and the right person to lead Choose Chicago 'above and beyond' and help write the next chapter of the city's tourism agency, he said.
One key stakeholder expressed support for the choice.
'Kristen Reynolds is a proven leader in the tourism industry and we welcome her to Chicago,' Mayor Brandon Johnson said in a news release Thursday. '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.'
A Texas native and Arizona State graduate, Reynolds spent more than a decade promoting Arizona as a tourism executive before landing on Long Island in 2015. Since taking the helm at Discover Long Island, the agency's budget has doubled and annual tourism spending has increased by $2 billion, Reynolds said. Last year the region, home to 3.5 million people, welcomed 42 million visitors — without a convention center, which is in development.
The marketing strategy Reynolds implemented, which relies heavily on social media, 'transformed' Discover Long Island and drove record-breaking visitation, according to a news release Thursday from the New York agency announcing her departure.
'We really kind of put Long Island on the map,' Reynolds said.
Choose Chicago was launched in 2012 under then-Mayor Rahm Emanuel by combining two bureaus into the city's official tourism organization. The not-for-profit gets most of its funding from state and city sources, with a budget of $34.7 million this year, according to an agency spokesperson.
Osmond, who stepped down after less than two years as CEO, earned $536,165 in 2023, according to the most recent Choose Chicago nonprofit tax return posted online.
Funding Choose Chicago is 'critically important' to its success, Reynolds said.
'I am very passionate about the need for diversified funding, and that's going to be a huge priority and goal,' she said.
Another priority for Reynolds is community buy-in for promoting Chicago as a tourism destination. She pointed to her podcast 'Long Island Tea' as a platform for giving Long Islanders a place to dish on their communities and be part of the marketing process for the region. Tourism, she said, improves the quality of life for residents.
While international visitation is a small percentage of the Chicago tourism pie, it will also be a priority for Reynolds, despite a political environment that may be challenging.
Industry analysts are projecting that Canadians, for example, who represent the largest segment of international travel to the U.S. and Chicago, will curtail travel south of the border in the wake of President Donald Trump's recently imposed tariffs and threats to annex Canada as the 51st state. Last year, there were more than 20 million Canadian visitors to the U.S., according to the U.S. Travel Association.
'There's a lot of international headwinds facing our nation right now, not just Chicago, but the entire country, and we're going to have to navigate that very carefully, and we're going to have to have a really strong approach,' Reynolds said. 'Chicago is in a very unique position internationally to be able to say we are welcoming, we do present and represent those American values of welcoming everyone. And I think that's really going to resonate internationally.'
Eden and Reynolds cited the upcoming Premier League soccer exhibitions in July and the rugby match between Ireland and the New Zealand All Blacks in November as boosts to Chicago's international tourism this year. They also pointed to the U.S. Travel Association's IPW 2025 trade show, which returns to McCormick Place in June for the first time in a decade, as a potential catalyst for international travel to Chicago.
Chicago is, of course, a convention city, which was not a part of the portfolio for Reynolds at Discover Long Island. Shut down during the pandemic, the convention business has been returning to McCormick Place, with 103 major events in 2022, 115 in 2023 and 112 last year, according to a spokesperson for the Metropolitan Pier and Exposition Authority. Selling Chicago as a convention destination will be high on the agenda for Reynolds.
While Reynolds comes to Chicago from New York, she has family ties to her new city. Her husband is from Chicago and her daughter attends Loyola University Chicago. On a professional level, she said the move represents the 'pinnacle' of her career, and an opportunity to make Chicago second city to none as a travel destination.
'I'm just really ready to shout how wonderful Chicago is from the global stage,' Reynolds said. 'The energy here is unmatched, and I'm ready to hit the ground running.'
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