City’s top tourism official stepping down after less than two years on job

Seven months before hosting the Democratic National Convention, Chicago is losing the head of its tourism marketing agency.

Choose Chicago President and CEO Lynn Osmond resigned Thursday, effective Jan. 31, just 20 months into her four-year contract to focus her “time and energies on a family health matter.”

She will be replaced, at least temporarily, by Choose Chicago Board member Rich Gamble, pending a nationwide search to fill what is believed to be the highest-paid public position in Chicago, with an annual salary of roughly $520,000.

A former president and CEO of the Chicago Architecture Center, Osmond was a surprise choice to lead the all-important agency charged with selling Chicago as a center for tourism and conventions and fending off hard-charging competitors like Las Vegas, Orlando and New York.

She was the first woman to lead the all-important agency and had no background in conventions and tourism. That wasn’t easy, considering that the last two CEOs — David Whitaker and Don Welsh — were widely viewed as experts in the insular convention and tourism industry.

But she called the job a “natural segue” because she already had been “selling Chicago throughout the world.” And she set out to prove it despite taking over during what Illinois Hotel & Lodging Association President Michael Jacobson called an “industry crippling pandemic.”

“She didn’t know some of the terminology that we use in our industry, but she learned very quickly. Every industry conference or training that I knew of — I saw picture of her there. She told me she was there. I give her credit for hitting the ground running and trying to learn as much as you can about the industry, then going out and selling and being able to talk the lingo of our big customers very quickly,” said Jacobson, who considers himself a friend of Osmond’s.

One such customer is the Radiological Society of North America, whose annual meeting is billed as “one of the largest and most impactful events” on Chicago’s convention calendar with 40,000 registrants, with 40% coming from outside of the U.S.

Earlier this week, the Oakbrook-based association committed to hosting its annual meeting in Chicago through 2032.

Given “the competitive landscape across the country right now with other cities trying to poach major shows like that,” Jacobson said, the radiology group “wouldn’t have renewed unless they had a strong quality relationship with the leadership at Choose Chicago. And that starts with Lynn’s personality and candor.”

The long-term extension capped a comeback year for Choose Chicago that exceeded what the agency called its “aggressive goals” by 24%.

Osmond’s sales team took credit for booking “over 2,100 future meetings and events representing 2.45 million hotel room nights” — 43% higher than the agency’s 2022 performance.

Thanks, in large part, to Soldier Field concerts by Taylor Swift and Beyonce, Chicago attracted 54.5 million visitors in 2023, raking in what Choose Chicago claimed was  an “all-time record in summer hotel revenue and collections.”

The bottom line: Osmond’s successor will be in a far better position than she was, Jacobson said.

“The last time they announced the CEO was leaving was in March of 2021. Their budget was cut because of lagging hotel taxes. … Most of our big-box hotels were still shut down because of COVID. We were talking, ‘Will conventions ever come back? Is Zoom gonna replace conventions? Is McCormick Place dead?’ We know the answers to those questions now. We’ve come roaring back,” Jacobson said.

“We have a great year ahead of us” with the Democratic convention, Lollapalooza and the radiology gathering, he added. “They have stellar leadership team over there right now that has instilled a lot of confidence in the industry. It’s an appealing position to go out and recruit for. Hopefully, we can bring in a leader that can capitalize off of that and grow them even more than they’ve grown in the past year.”

Osmond did not return phone calls.

Chicagoland Chamber of Commerce President Jack Lavin called Osmond an “outstanding advocate and champion” for the tourism and convention industries.

“Any time there’s a change, there’s gonna be a learning curve. It’s unfortunate that she has to leave. But, if she has a personal family matter, she has to take care of it,” Lavin said.

In a press release, Osmond hinted strongly that she can no longer give what the pressure-cooker job demands.

“Right now, I have to put my family first. … I know this is the right decision for me, my family and for the organization ... as we gear up for a very busy year with the 2024 Democratic National Convention coming to town,” Osmond was quoted as saying.

Gamble also could not be reached for comment.

Shortly after taking office in 2011, former Mayor Rahm Emanuel merged the city’s three tourism marketing agencies into Choose Chicago.

The super-agency proceeded to open more offices around the nation and the world, with help from an increased marketing budget — at first locally and then with the help from the state when the Illinois budget stalemate finally came to an end.

Emanuel also worked with labor leaders to broker two rounds of work-rule changes at McCormick Place that made Chicago more competitive.