View From Afar S1, E13: IPW 2025 | Kristen Reynolds, President and CEO of Choose Chicago

I’m Michelle Baran, deputy editor at Afar. Welcome to View From Afar, a podcast that spotlights the people and ideas shaping the future of travel. And in this special series, I’m coming to you live from the floor of IPW, the annual travel conference organized by the U.S. Travel Association to share the best of America with the rest of the world.

In this episode, we’re talking with Kristen Reynolds, the new president and CEO of Choose Chicago. Kristen officially started the role on May 5th, and brings 27 years of tourism experience to the Windy City.

She’s a Texas native who spent nearly eight years with the Arizona Tourism & Lodging Association before taking over Discover Long Island in 2015. During her decade in Long Island, she transformed that organization, growing tourism to a $7.5 billion industry that brings 42 million visitors a year—and that’s without a convention center.

We talk about how she’s bringing that growth mentality to Chicago, what’s on the horizon for the America 250 celebrations—and the benefits of hosting industry events and conferences like IPW.

Transcript

Michelle: Alright, well welcome Kristen. It’s so great to have you here.

Kristen: Thank you so much.

Michelle: So you’ve had quite a journey from Texas to Arizona to Long Island and now Chicago. What drew you to each of those markets and how have they shaped your approach to destination marketing?

Kristen: Well, I went to Arizona because I went to Arizona State and I went to the Walter Cronkite School of Journalism at Arizona State. So that’s what drew me there and I never really expected to stay there, but I fell in love. I kind of stumbled into tourism. I worked for a PR agency and a couple of our clients were tourism related, so I stumbled into it like so many of us do. And my job was to do FAM tours around the state for the state tourism office. No better way to fall in love with the state than that. I was riding horses and whitewater rafting and hot air balloons. I’m like, this is great. I love this industry.

And then I was there for over 20 years and I worked at the state tourism office, I went to a resort. I worked on property, then I went to the trade association and then eventually became the lobbyist for the state tourism industry. And I kind of felt after 20-plus years, I had done everything I could do in the state and I wanted to spread my wings. And on a whim, actually this job in New York came up and I was like, Long Island seems cool. I was a single mom. I had a third grader and a sixth grader. The other thing Long Island is known for, other than the Hamptons, is the education. An incredible place, you know, New York education for my daughters.

So I just threw my name in the hat, like on a whim. Eight months later, I was moving to Long Island and I had a two-year contract and that’s how long I expected to stay. And 10 years later. I love it. My kids will tell you that they’re Long Islanders. You know, they’re New York girls. They were raised there and, but my last one is graduating from high school and I had—same thing, I rebranded the destination. I doubled the budget. We got funding for what will be Long Island’s first convention center and kind of felt like I had done everything I could do on Long Island and my youngest daughter’s graduating from high school now, and we’re about to be empty nesters, so I started to think, what’s next?

And there’s a lot of opportunities for these roles across the country. But I wanted to go someplace where I had a personal connection and I wanted to live. My husband, who I married four years ago, met on Long Island, he’s actually from Chicago. And so we would come back here all the time to visit. And my in-laws are here and our daughter goes to Loyola. So once again, I kind of threw my hat in the ring on a whim. And the rest is history.

Michelle: So yeah, here we are. Here, we all are in Chicago. And of course, first and foremost, we have to talk about the Pope.

Kristen: Oh my God. Of course.

Kristen: And I say, my God. Amazing. That was my first week. Everyone’s like, wow, you work fast. *Laughs*

Michelle: Exactly. Congratulations. So obviously it could be a big tourism boon for Chicago, maybe it already has been. What’s your take on how to best capitalize on that kind of excitement and exposure?

Kristen: So the easiest thing is, Chicago is on the tip of everyone’s tongue right now. Everyone, no one says the word pope without the word Chicago in it, which is incredible, the Chicago Pope.

So, you know, not only is he a great sports fan, and that’s a really wonderful opportunity, but it gives everybody that inclination to find out more, what is Chicago about? So we just launched our brand new campaign, Never Done, Never Outdone Chicago.

And this is like a global caveat for us to share that story because just very luckily, having the Pope from Chicago puts a global spotlight on our city and gives us the opportunity to tell people more about

Michelle: So with that spotlight, what are some of the most exciting new hotels, museum openings, events or happenings coming to Chicago that you want visitors to know about? When they come on their Pope Leo tour, what else can they do while they’re here.

Kristen: Well, I mean, Chicago is such, you guys are here, right? It’s such a beautiful city. So even if you just come here and enjoy the scenery and the lake and, and the iconic things that we’re known for, like the Navy Pier and the Field Museum and the Art Institute and the Bean, you know, you’re going to have an amazing time.

But honestly, the culinary scene is really—it continues to rise every year. We just hosted the James Beard Awards last night and we had two winners from Chicago, which is incredible. The Bear has put us on the culinary map. The new season starts next week. I can’t wait.

But there’s some new things happening also. We’re getting ready to open the Obama Center. That is going to be in 2026. It’s going to be the best presidential center that’s ever been made because it’s on the south side and it’s more about the community. There’s going to be a garden, an athletic center for local kids to come enjoy. So it really is going to be a new staple for our city.

And then we’ve got Route 66, which, we are the start of Route 66, and that’s going to be next year, as well as America 250. Yeah. There’s just a lot happening in this city, and it’s a pace that is sometimes mind numbing.

But the great thing is if you can’t get it all in one trip, there’s plenty to do to come back over and over again.

Michelle: It’s so true. And you mentioned like a lot of these sort of hallmark experiences, that Chicago is known for. So how do you balance sort of promoting the things that everyone already knows and dreams about when they come to Chicago with encouraging travelers to get off the beaten path a little bit and explore some of the lesser known corners and aspects of the city?

Kristen: Yeah, it is a balance and I would say that, you know, you’re never going to tell the first time or sometimes even second time visitors not to go to the Bean or not to go to the, you know, the Tilt or one of their great Skydeck attractions.

The great thing is, Chicago’s been such an incredible city for so long. You know, we were named the best big city eight years in a row. We’re going for that ninth year. So people do come back over and over again, and I think when people start to come back over and over and again, that’s when you can start to say, listen, there’s always something new for you to explore. We have 77 different neighborhoods. This is when you go to Chinatown. This is when you go to Little Village. This is when you go to Andersonville or Pilsen. And it’s really a great opportunity for the repeat visitor to get out and about.

Michelle: Yeah, absolutely. And you mentioned America 250. I mean, again, just one of the many things that are exciting both for Chicago and in some aspects for the country as well. So what are the parts of Chicago’s history and the role it plays in the greater country’s history that you’re sort of most excited about celebrating with America 250 on the horizon.

Kristen: Yeah, I think, you know, Chicago—we have so much history here, obviously. Lincoln, you know, was a senator here, but. But beyond the history, America 250 is really about America’s evolution over the last 250 years. And Chicago is a big part of that. That Never Done part of our campaign is about how we’ve constantly evolved from an industrial town to, you know, an innovative town and technology and tourism, and what I think we’re going to highlight, you know, looking forward with Illinois is going to be our diversity and really a place that still celebrates diversity, celebrates inclusion, celebrates equality, all of those things that America was built upon still exist and are still welcomed here in Chicago.

Michelle: With all these great things happening and on the horizon, like you said, some of them, you know, accidental miracles, maybe you’ll call them

Kristen: Stars aligned, got some good karma.

Michelle: What are some of the challenges that Chicago’s tourism industry faces? What are some of the, you know, difficulties?

Kristen: I think, you know, our biggest challenge is probably a false narrative that’s out there about our city, which is why I’m really excited about this new campaign. Having lived here for six weeks, my first month here, I didn’t have a car. I left my car in New York, so I took the bus, I took the train. I’ve been walking all through Grant Park. When I went to Beyonce, it was like 11 o’clock at night by myself. And, and listen, every major city has our challenges. Every small town has its challenges these days from a safety perspective, but my personal experience and the 55 million visitors that come every year is that Chicago is a safe city, we’re a welcoming city, we’re a beautiful and clean city, and our job is to really take control back of that narrative. And I think we’ve done so this week, and show people what Chicago’s really all about.

Michelle: So as a California girl, I have to ask, how do you deal with trying to, you know, transition Chicago into a year-round market, because obviously winter in the Midwest is a thing. We’re here, the weather’s been amazing and, you know, but it’s not like that necessarily—

Kristen: —not like that year round. Yeah. And that’s true. And you know, I learned this when I was actually in Arizona, when I was in Phoenix because Phoenix was definitely settled during the peak season. Okay. You don’t go there in the middle of June, July, or August, and realize, this is a great place.

So we learned that during those months, you know, the prices go down. Yeah. And a lot of the locals and, and the Californians will come because you want those great rates and you can get the same thing that people are paying triple for during a different time of year. So it’s seasonality and your customer changes. So during those winter months, we’re not going to tell Californians to come to Chicago.

Kristen: That’s not, we’re going to tell you to come here when it’s peak season and you’re going to pay the most. During those times is when we’ll get our locals to come out and we’ll look at that regional market and that drive market and make sure that people that want Chicago access and availability but don’t want to deal with the crowds—this is when it becomes their Chicago.

Michelle: Right. I heard this great tip once that different cities, like they have a restaurant week often, and it’s often in the winter. And it’s because you want—

Kristen: That’s for the locals.

Michelle: It’s for locals and if you’re a smart traveler, a smart tourist, you will go during that restaurant week because it’s also when you can access all these James Beard Award-winning and Michelin-starred restaurants at a great value.

Kristen: Those low season months are when locals reclaim their city from the tourists. And it’s also a great opportunity for our meetings and conventions. That’s when we can have some great value opportunities for people that want to have a meeting in Chicago.

Michelle: So what part of your job do you think people are sort of unaware of the things that go on behind the scenes that you’re doing that are sort of invisible but that actually have sort of concrete, tangible outcome for the travel experience? And I’m not including the fact that you obviously were involved in getting Pope Leo nominated.

Kristen: Yeah. This job is really interesting. I don’t think people realize the politics of this job. When you’re interviewing for this, people are like, well, what is your convention sales experience? Or, what is on your mind? I’m like, I’m not selling conventions. I have a very capable sales team that does that. I have a very capable marketing and communications team. My job is to make sure that I’m amplifying what the team is doing to our stakeholders and to our elected officials. I think we’ve all seen what’s happening when elected officials are unaware of the economic impact of our industry. And when that happens, it’s too late. By the time they’re asking questions, it’s too late. My job is to make sure everybody understands the value of what this organization does and what this industry brings to our local community, and so that we can protect our funding source, and so that everyone else on the team can do the job.

Michelle: So how are you getting that welcoming message out? How are you communicating that Chicago is a welcoming

Kristen: It’s a lot of personal one-on-ones. My schedule’s open, I meet with people. I go to every meeting request. I go to Rotaries, I go to libraries. Where do you want me to come and tell you about the importance of Choose Chicago or the tourism industry?

I do a lot of touch points with all of our elected officials at every single level because you never know when they’re going to rise to that level. It’s really constant education, and it takes a lot of work. But if you believe in what you’re doing and you believe in your product, which I do, I’m lucky enough to have a product like Chicago. It’s an easy sell. It just takes a lot of time.

Michelle: And I’m just curious, what are your biggest international source markets?

Kristen: Canada is our biggest, you know, market and so it’s been tough obviously for Canada, for the United States this year. But we still have great support in Canada and Canada still—we still love each other. And Europe is a huge one and Latin America, so we’re really actually kind of up in those numbers. Latin America, we’re slightly up. Europe, we’re flat. I keep saying flat is the new up.

Michelle: Yeah, right.

Kristen: But there’s still a lot of interest in Chicago, you know, and maybe more so than others, but again, because we are that city that embraces diversity and, you know, and is still representing a lot of those American values—

Michelle: I mean, I’m going to be honest, as being out walking around downtown, there doesn’t seem to be any shortage of travelers going to Chicago from all over the world.

Kristen: We had 55 million visitors last year and we had over $20 billion in tourism economic impact, which was a record. So, we’re on an upward trajectory. We want to just keep going.

Michelle: Yeah, yeah, absolutely. And so, we’ve been asking a lot of the DMOs to, you know, 30-second challenge, convince me, make me wanna go to your destination. Obviously we’re here so you—*laughs*

But the pitch you give your friends. So tell me why you should come visit and what we’re going to do, like we’re old pals.

Kristen: Okay. My friends, I would say come visit me, because I’m here.

Still, it depends on what you want to do. I’m a shopper. So the Mag Mile for me, still iconic. There’s nothing better. So we’re going to eat great food, we’re going to drink great wine. We’re going to be welcomed everywhere you go. Everyone’s going to be friendly. We’re going to go shopping, we’re going to walk around the city.

And I just feel like Chicago is comfortable, you know? And that’s not always the case in every city. It’s not difficult. It’s not challenging to get around. It’s not hard to learn the city. It’s on a grid. It’s really easily walkable.

Michelle: I’m not sure people realize how walkable Chicago really is. I think people kind of assume it’s a larger city and it’s like, no, it’s so walkable and the mix of city and green space and the river, like you have a really great mix.

Kristen: I love it. And I’m still learning it. Because you know, being new, I’m still—

Michelle: Right. You’re still a bit of a tourist here.

Kristen: Exactly. My apartment that I got is right off of Michigan Avenue by the Tribune building and I’m like, it’s kind of dangerous for me. *Laughs* Lock away my credit cards right now. I walk out, I’m immediately in all these iconic stores. But it’s just the energy. You immediately feel the energy here and it’s just so fun. It’s just a really fun city.

Michelle: Yeah. I totally agree. Well, thank you so much for being with us.

Thanks for joining us for this episode of View from Afar. In the show notes, you’ll find links to everything we discuss today as well as Choose Chicago’s website and social media handles and our recent Chicago coverage. And be sure to follow along this week to hear more interviews with industry experts.

You can find more Views From Afar on afar.com. And be sure to follow us on Instagram and TikTok. We’re @AfarMedia. If you enjoyed today’s exploration, I hope you’ll come back for more great interviews. Subscribing always makes that easy. And be sure to rate and review the show on your favorite podcast platforms. It helps other travelers find it.

This has been View From Afar, a production of Afar Media. The podcast is produced by Aislyn Greene and Nikki Galteland, with assistance from Michelle Baran and Billie Cohen. Music composition from Epidemic Sound. This podcast is part of the Airwave Media podcast network. Visit AirwaveMedia.com to listen and subscribe to their other fine shows like Culture Kids and The Explorers Podcast.