Spotlight on Kristen Reynolds, CEO, Choose Chicago

After an 18-month collaboration with agency MMGY, Choose Chicago in June 2025 unveiled its $4 million advertising campaign, “Never Done, Never Outdone.”

“We're kind of dropping some of that Midwest nice and humility and bringing some swagger into our destination,” says Kristen Reynolds, president and CEO of the Windy City DMO. “And it's OK to say that we're the best at what we do.”

It didn’t take long for unforeseen circumstances to make Choose Chicago prove it was up to its new billing. In July 2025, about a month after the new branding launched, and only two months into Reynolds’ tenure, United States Immigration and Customs Enforcement descended on Chicago.

Suddenly, the destination looked like “a war zone” with scenes that didn’t represent Chicago’s true nature, says Reynolds.

During one memorable 24-hour emergency session, Reynolds and her team developed an action plan to tell Chicago’s true story. The DMO leaned into one today’s central marketing themes, authenticity, by working with everyday citizens for the “All For The Love of Chicago” initiative.

“Our community was so tired of being defined by other people who aren't here,” explains Reynolds.

Fortunately for Choose Chicago, ICE is not out of the picture, but the successful resilience remains. Rather than abandon the local-fed content, Choose Chicago has increased its presence to include a podcast.

As last year’s events proved, destinations need to remain proactive to attract visitors. Chicago brings in 55 million out-of-towners each year and has been ranked the best big city in the U.S. nine straight years by Condé Nast, but Reynolds says there is room for growth, particularly in the international market.

Demonstrating tourism’s importance to the local economy, the Chicago City Council recently approved a Tourism Improvement District (TID), a move that will provide a stable and dedicated funding source for Choose Chicago.

“This is a transformative moment for Chicago’s tourism industry,” says Reynolds. “With the TID in place, we now have the enhanced resources to match the ambition and vibrancy of our city. This investment will allow us to amplify our marketing efforts, attract more conventions and events, and ultimately deliver significant benefits to Chicago’s economy and communities.”

ETS spoke to Reynolds about an eventful first year at the helm of Choose Chicago.

What makes “Never Done, Never Outdone” an appropriate message for Choose Chicago?

We wanted to convey ourselves as a city and as a destination, something more than just a tourism campaign and a rallying cry for our city. We just feel like it perfectly embodies what Chicago's all about. We're constantly evolving. There's constantly something new to do here where there's new attractions, new restaurants, and a lot of growth and innovation. We've got the Obama Presidential Center coming. We've got new events every year. So “Never Outdone” is a great way to describe that our city is always vibrant and growing.

Since you brought it up, can you share the impact the Obama Center will have on the city?

The opening of the Obama Presidential Center, which is slated for Juneteenth, is going to be a game changer, not only for Chicago, but particularly for the South Side of Chicago, where it's located. The timing couldn't be more perfect. It's the 250th anniversary of the Declaration of Independence signing. It is the 100th anniversary of Route 66, which started in Chicago, se have a lot of fun narrative around that, and now we have the Center.

It’s not called a presidential library because Obama was the first digital president. So, it really is resetting the tone for those kinds of attractions.

How are you spotlighting some of the areas like South Side that are not typically tourist attractions?

We have a really cool program called the Chicago Greeter Program. It is free tours in all of our neighborhoods. You just sign up, you can be one person, you can be 15 people. And we completely fund that and provide it for people who might not be comfortable going out and doing something on their own.

How are you using analytics to guide your marketing?

We benchmark all our activities and measure growth in a variety of ways. So data and analytics drives everything that we do. We are a data-driven organization. Before we make any strategic decisions, we look at all our resources from Tourism Economics, and have been using data on origin markets and studying migration data to how the population is shifting.

Describe your leadership style.

I like to be an innovator. I like to try new things. I like to be an early adapter. If it works, great. And if it doesn't, you fail fast and move on, but you can say you tried it. I always say the people that thrive in disruption are disruptors. So that's who we want to be and strive to be.

Photo Credit: Choose Chicago