
All for the Love of Chicago: Rethinking the Destination Experience
In this episode of Associations NOW Presents: Industry Partner Edition, recorded live at ASAE’s Annual Meeting & Exposition in Indianapolis, host Sharon Pare of High Road Solutions welcomes Kristen Reynolds, president and CEO of Choose Chicago, for a conversation about the changing meetings and tourism landscape and what makes Chicago a compelling destination for associations. Reynolds shares her path to Chicago and discusses the city’s tourism momentum, from record-breaking convention attendance to major developments including the Obama Presidential Center, a revitalized Magnificent Mile, a new O’Hare terminal and new sports and entertainment projects. She also highlights Chicago’s accessibility, hospitality community and McCormick Place, as well as how Choose Chicago works with associations to create memorable experiences that extend beyond the convention center. The conversation explores the role of authentic storytelling in destination marketing, including the “Never Done, Never Outdone” campaign and the resident-driven “All for the Love of Chicago” initiative, which gives Chicagoans a platform to share their own stories about the city. Check out the video podcast here: https://youtu.be/Qo5DGBRhMuo This episode is sponsored by Choose Chicago. Associations NOW Presents is produced by Association Briefings. Transcript Sharon Pare: [00:00:00] Welcome to this episode of Associations NOW Presents: Industry Partners Series, an original podcast series from the American Society of Association Executives. I'm Sharon Pare, Partnerships Director at High Road Solutions, a HubSpot agency. We're recording live here from Indianapolis today for ASAE's Annual Meeting and Exposition, the Super Bowl of all association meetings. Today's episode is sponsored by Choose Chicago, and today we are excited to welcome Ms. Kristin Reynolds. She's the CEO and president of Choose Chicago, so I want to welcome you in. Kristen Reynolds: Thank you so much. It's exciting to be here. This is my first ASAE Annual Convention, and it's awesome. Sharon Pare: So now that it's your first time being here, how do you feel? What's the energy like? What are you hearing on the floor? Kristen Reynolds: Well, we're very excited, and we're mostly excited because Chicago is actually hosting in 2028. Yep. So we're here soaking up all the information, what's working, what people [00:01:00] love, what we can bring more of, how we can wow them when they come to Chicago. But really, there's a lot of excitement. There's a lot of energy on the show floor, but it's a state of transition. Right. There's a lot of change in our industry and in the world, and, and that can be difficult sometimes, but it's exciting. Sharon Pare: It's exciting, and talking about some of that change, is there something on the floor that maybe gives you a little bit of concern? Is there anything you're worried about? Kristen Reynolds: Well, I think everything gives... When you're a CEO, everything gives you concern. I live in a constant state of fear, and I think that's how you stay sharp, actually. But yes, there's a lot of things, technology, how it's advancing. You don't know how that's gonna change. Right. Newer generations coming into the workforce, especially in association memberships with are they getting what we used to get from being part of associations? Are they feeling that community? And how do we continue to bring in younger generations? There- there's a lot of those conversations going on right now, but really [00:02:00] mostly positive. This is a resilient business. Nonprofits are resilient organizations. Yes, they are. And I feel good about it at Choose Chicago because I always say, "The best people to navigate times of disruption are disruptors." Sharon Pare: That's Kristen Reynolds: right. And that's what we're all about. Sharon Pare: One thing I wanted to do before we really dig into everything is I know you've built your career in different states all around the United States. I know you started in Arizona maybe. That's right. That's right. And then at one point you were in- Kristen Reynolds: New York ... Sharon Pare: Long Island. Kristen Reynolds: Yes. Sharon Pare: And w- I don't know if you say Long Island or- Long Island ... how do you say it? Long Kristen Reynolds: Island. Sharon Pare: And then- Kristen Reynolds: And now Sharon Pare: Chicago. You chose Chicago. So tell us a little bit about Chi-Town ... Why did you choose Chicago? Kristen Reynolds: Why did I choose Chicago? I grew up pretty much in Arizona. I went to Arizona State. Both my daughters are Sun Devils, and so my family lives there. Going to New York was a big jump, but from my position, New York was like the pinnacle of tourism. Long Island's an incredible place to raise a family, but with still access to New York City. I was there for [00:03:00] 10 years, and then I became an empty nester. And I was, I think I'm too young to be on my front porch in a rocking chair on Long Island. I had another gig in me, and my husband is from Chicago. Mm-hmm. So here's a little tidbit. I say this all the time. I used to say he's from Chicago, born and raised. He went to Loyola Chicago, and my stepdaughter's there. But now that I live in Chicago, I say, "My husband's from the suburbs of Chicago," because that means a very different thing to Chicagoans than being from Chicago. So when the job came up, it just happened to be the perfect timing, and I really only wanna work for and represent a city that I feel a connection to and that I believe in, and Chicago is the best big city in the US for nine straight years. So I feel pretty lucky. Sharon Pare: That's a pretty lucky job that you have there. And before we talk about this later, I wanna mention that you're behind the mic today as a guest. Yes. But you've hosted two of your podcasts now. Yes. One when you were with Long Island, [00:04:00] which ... What was the name of it again? Yes. Kristen Reynolds: We started it during the pandemic when we couldn't market, and we wanted to, to story tell, and it was really the beginning of podcasts. It was called Long Island Tea. Oh, Sharon Pare: I love that. Kristen Reynolds: Where we spill the tea on living your best Long Island life. Okay. And it was a play on, obviously, Long Island Iced Tea, and it was great. I'll tell you, the first several f- few years it was sponsored by Long Island Wine Country, so we were contractually obligated to drink wine during the podcast. And so- Sharon Pare: It does not sound like a bad deal at all Kristen Reynolds: ... it was really fun. Then we had to realize, we had to kind of rein that in a little bit. That's okay. Sharon Pare: Hone it in sometimes. Kristen Reynolds: And then also I started another podcast there called The C-Suite Tea. Sharon Pare: Oh, okay. Kristen Reynolds: Which is still going on, which is fantastic. My COO, who's now the CEO, continues to take that over, and that's where we just would give C-suite advice because people really wanted to know more about it. And then when I came to Chicago, it was like, "Are you gonna start a podcast?" And I wasn't really planning on it, and then we launched this new campaign, and one thing led to another, and we now have a podcast in Chicago. Sharon Pare: So let's talk about Chicago. You [00:05:00] just said that Chicago's been named the best city for the last nine years. Yes. You had a record year for tourism in 2025. So when you look at those numbers, what are they telling you now about the momentum that you're seeing in the city right now? Kristen Reynolds: Yeah. That's the perfect word, and I'm, I get chills, honestly. You really do. But there is- I, I just got chills- ... goosebumps ... talking about it because I just feel so lucky to be in Chicago in this moment, and that's what we keep saying right now is Chicago is having a moment. We did just recently open this small attraction, you might have heard of it, called the Obama Presidential Center. No big Sharon Pare: deal. Kristen Reynolds: But there's so much more than that. There m- the Magnificent Mile, which is the Michigan Avenue, is ... There's so much resurgence. They just opened the Hello Kitty Cafe. Oh. And the first Cube in the US, and the Candy Hall of Fame is coming. There's so much development happening there. The Chicago Fire is building a new stadium, and the 1901 Project, which is the United Center, is having a complete renovation. There is so much momentum in Chicago, and from a meetings [00:06:00] and convention standpoint, we're seeing it as well, that the attendees this year, almost every single one of our meetings and conventions have broken records in attendance. Sharon Pare: That's amazing. Kristen Reynolds: And that's because there's so much for people to do and see when they're in the city. So it all builds on each other, and it all connects in the success of what we're seeing in our numbers. But we've had a record-breaking summer. Our summer this year continues to just soar above our comp set, which we're very lucky. Even without ... We are one of the non-host cities for the World Cup, and we are one of the only destinations in the US that actually saw an increase in June, almost double digits. It's really saying something about what the city has to offer. Sharon Pare: So you've shown up on all these lists. I know you've talked about some of the new developments that are coming up in Chicago right now. But what is it right now that are bringing these associations back? Now I ... Obviously- Mm ... those record number breaking attendee numbers are coming in. But what's something different today that maybe wasn't there five or 10 years ago about the city? Kristen Reynolds: I do think it's [00:07:00] a lot of the surrounding development that I just mentioned. But ultimately, the reason why we're a successful convention destination is we have McCormick Place, the largest convention center in North America. So we have the infrastructure. The infrastructure of Chicago, it just works. We have two international airports. Our airport, O'Hare, was just named again the busiest airport in the world. Sharon Pare: It sure is. Kristen Reynolds: I know. There are pros and cons, right? When you're landing, it might take you a little bit long to taxi. And we're building a new terminal at the O'Hare Airport. So our location in the center of the country actually makes it so accessible, so easy to get there within three, three and a half hours from pretty much anywhere. Plus, we have such a great regional drive market to be able to drive that attendance. Our team is really gelling. Our team at Choose Chicago I think is the best in the industry when it comes to customer service. We respond. What I love about Chicago, and you said I've worked in multiple different states. I'll tell you, in New York, [00:08:00] kind of come or don't. You know what I mean? We're New York, so good luck. Sharon Pare: Yep. Kristen Reynolds: In Arizona, it was very much why wouldn't people come to Arizona? We're sunny all the time. Right. What do you mean we have to tell people? But Chicago competes. Chicago as a city- Compete, they wanna win, and our whole community rolls up their sleeves and comes together to make meetings successful. Sharon Pare: Now I wanna talk a little bit about some of the infrastructure. You s- you mentioned it before, no big deal, the Obama Presidential Center, the 1901 Project, the Chicago Fire Stadium. But what do you think these recent developments are going to ... For what are the attendees when they come to the city, what is gonna surprise them the most about some of these new investments to the city? Kristen Reynolds: And I think it's the investments, but also it's the events and the festivals. We just hosted Lollapalooza. Sharon Pare: I heard that was amazing. Kristen Reynolds: Ah. I'm telling you, all my college age kids and their friends all went, and it's an amazing city. Again, the fact that we can bring in 400,000 people plus in a [00:09:00] tight area in four days. Sharon Pare: I've seen pictures. Kristen Reynolds: And really just have wonderful energy. Yes. Wonderful experiences. There were ... You don't hear about incidents or ... It is really just such a ... It's beautiful. It's a magical experience. The skyline behind it and, and everybody walking around enjoying the city. What the city has to offer as far as infrastructure is we just launched our new campaign, it's called Never Done, Never Outdone. Mm-hmm. And that's really what we're talking to people about. Every time you come, we are never done evolving, we are never done growing and building, and we won't be outdone for what we wanna deliver in our hospitality. Sharon Pare: Just like you said, your city is always earning that right to be the best city for the last nine years. So I wanna go back to not just Lollapalooza- Yeah ... but just the experience of the city. When an association chooses Chicago, how do you help them take that experience beyond the convention center, the four walls? I know that we're live in one right now. Yes, yes. But what is it that your city does to [00:10:00] give everyone that experience? Kristen Reynolds: I think that's our sweet spot or secret sauce, however you wanna say it, and that's what Choose Chicago is best at, as we know that people are coming to Chicago for the city of Chicago. We are the host of the annual James Beard Awards. We are a culinary city. Sharon Pare: Yes, you are. Kristen Reynolds: It's where The Bear is filmed, right? For a reason. So when people come, we know they wanna eat out. They wanna have these incredible experiences. They wanna go to Navy Pier. They see the water. They wanna go out on the boat cruises. Oh, you have to go on the boat cruise. The architectural... If you have not gone on an architectural boat cruise, have you ever really been to Chicago? No. No. Obviously. You have to do this. Sharon Pare: Took me 10 times. Kristen Reynolds: It took me, it took me several too- Yes ... going back, and then finally I was like, "Gotta do this boat cruise." Sharon Pare: Yes. Kristen Reynolds: And then I'm like, how did it take me so long? But that, that is the experience that we know drives success for meetings and conventions, and what attendees are looking to do. Outside the walls, yes, you wanna come in, but the vendors wanna have a great place to host their top clients. The attendees want something that they can have pre [00:11:00] and post with their families and extend their trip, and that's really what Chicago does best. We have a great client services department that many of them have been there for more than 20 years. We have relationships with every single person and business in our city, from the medical district to the restaurants. So anything that you're looking to do to make your event successful or make more excitement for your attendees, that's what we deliver. Sharon Pare: Let's take a quick break to hear a word from our sponsor. Ad Read: Chicago, a city connected. Not just by train lines or shorelines, but by the drive to never settle. We talk less, dream bigger, and never stop pushing. We change the course of rivers and the course of history. When we build things, the world looks up. Here in Chicago, [00:12:00] world-class venues, trailblazing industries, and captivating experiences come together to create events that redefine what's possible. We don't just host meetings, we transform them. So welcome to the greatest city in the world. Because in Chicago, we are never done and we are never outdone. Sharon Pare: I will say, just being a frequent visitor to Chicago, I always feel the warmth. Yes. Especially coming from the East Coast. Yes. You get that Midwest warmth with that swagger. Yes. Like that never out done. Kristen Reynolds: Never outdone. Sharon Pare: Exactly. You got it right. Kristen Reynolds: Yes. Sharon Pare: Awesome. So if somebody listening is thinking about Chicago for a future meeting, what do you want them to know about where Chicago is headed? Kristen Reynolds: I want people to know that Chicago is the best big city in the US for a reason. But we also ... What you just said is so perfect, Sharon. It's a big small city. [00:13:00] So the hospitality is genuine, that Midwest nice is real. Everybody wants to help you when you come in. It's, like I said, moving from New York, at first it was a little off-putting. You're like, "Is this real? What's your angle? What do you want? What are you talking?" Sharon Pare: Yeah. Kristen Reynolds: But no, it's real. It's genuine. And I want people to know that when you come to Chicago, you're going to have the best experience. The number one thing, especially first timers to Chicago say is, "Wow. Wow, I had no idea." So it's not gonna be the best kept secret for much longer. Investments and housing and relocation and corporate relocation, it's going through the roof right now. So if you're thinking about it, now's the time to book. Sharon Pare: So I know you're a natural born storyteller, but let's go back to your podcast. Okay. I wanna talk a little bit more about what is the story that you're trying to tell differently now on the podcast, something you're trying to go deeper on with your Kristen Reynolds: All Sharon Pare: for the Love- Yes of Chicago? Kristen Reynolds: Yeah. So we launched this campaign on social media called [00:14:00] All for the Love of Chicago really during this time of political strife when there were federal agents, and there was just a lot of misinformation coming out about our city. And we had just launched Never Done, Never Outdone, and a lot of our stakeholders were, reached out and said, "Kristin, we need help from Choose Chicago." But when you wanna tell a genuine, authentic story about your city, it's not gonna come from the marketing organization always. So, we launched All for the Love of Chicago on TikTok and Instagram to give the camera to the people. So we told all of our residents, all of our visitors, "Send us your video about why you love Chicago from your words, no prompting, and then we just repost it." And it was so popular on social that we decided to launch the podcast, All for the Love, to have that long form storytelling. So it's very different than Long Island Tea, which was mostly just internal. Each episode we bring in a Chicagoan. We bring in somebody that's gonna tell you a story, a behind the scenes, we pull the curtain back. Mm. And it really is to showcase [00:15:00] from the Chicagoan's perspective what our city is all about, and to take ownership and control back of our story for our residents, and to give you really genuine information. These days with AI and ... I can't tell you how many videos I send to my college-aged daughters and they're like, "Mom, that's not real. That's AI." I'm like, "What?" Sharon Pare: Are you admitting guilt right now? Kristen Reynolds: I am. And I'm like, "How?" So to know what's real is so important in today's environment. That's what we're, that's our goal, is to show you the real Chicago. And once you know the real Chicago, th- there's no denying it, you will love it. Sharon Pare: So I think this is a perfect segue for us to know the real Kristen Reynolds. Okay. So I've got a few questions for you. Kristen Reynolds: Okay. Sharon Pare: My first one is, what's your perfect Saturday in Chicago? Now, I know there's a song. There's a whole song- ... about Saturday in the park by Chicago. Yes. So I'm thinking about that now, but Kristen Reynolds: what's- Now that’s in my head. Sharon Pare: What is Kristen Reynolds' favorite Saturday thing to do in Chicago? Kristen Reynolds: I have two dogs, [00:16:00] and so I- luckily, they force you to get out and walk a lot, and I live right in the heart of downtown Chicago. Oh, okay. I- Sharon Pare: City dogs. Kristen Reynolds: Yeah they're city dogs. Yes. Yes. And so I love to, I walk along the river. I love to get up, walk along the river. There's so many places. It's a very dog-friendly city. You can sit outside, have brunch. I'm a big bruncher. I love to go to Lincoln Park- Okay ... for brunch because they have a wonderful farmers market there on the weekends especially. You walk around. There's always pop-ups, and so it's so great. And then come back, and then h- honestly, the lakefront. That's one of Chicago's... It really is what sets it apart, is that beautiful lakefront. Yes. Enjoying the lakefront. There's trails. There's biking trails, running trails. And then y- to catch that sunset, there's nothing like it. And then maybe a glass of wine. But a speakeasy. I've, I'm feeling a theme, f- from, from mimosas to speakeasy wines. But no, there's so much to see and do, and it's honestly the biggest [00:17:00] challenge of representing a city like Chicago is there is so much to do- So much ... and see, and I'm trying to do it all, and it's, not enough fits into one Saturday. Sharon Pare: Not enough fits into one Saturday. So if somebody only had a Saturday, and it was- Yes their first time in Chicago- Yes ... and you're like, "There's the one thing you need to do," what would it be? Kristen Reynolds: So I actually do this a lot. Okay. Ever since I've s- become the CEO there, every... I can't tell you, at least 10 people have come to Chicago that I know for the first time because they've seen me posting about it. Yeah. And they're like, "We're coming." So you have to go to the Bean. Sharon Pare: Okay. Kristen Reynolds: You have to get the obligatory reflection picture in the Bean. And then the, what I love about the Millennium Park area where the Bean is, and which kind of flows into Grant Park, is, again, you've got the waterfront. You've got Buckingham Fountain. To go through there, I think one of the surprising things about Chicago is the public space and the open park area. It is so beautiful all year round 'cause in the winter, by the way, it turns into the ribbon ice skating rink. Really, I send everyone to downtown. [00:18:00] Go down Mag Mile. Check out the Bean. Go to Grant Park. Go to the fountain. Really enjoy our outdoor public spaces. Sharon Pare: All right. Second to last question. Kristen Reynolds: Okay. Sharon Pare: I know that your husband is from the suburbs- Suburbs ... of Chicago. Yeah. But what is the most Chicago thing about you? Kristen Reynolds: You know what? I live steps from Mag Mile, and every now and then somebody will say, "You walk around the city all the time. Is it safe?" I'm like, the scariest thing about living in Chicago is walking by the stores with my credit card and not taking it out. I say that legitimately. The biggest Chicago thing about me is I love to shop. Sharon Pare: Oh, yeah. Kristen Reynolds: And I love the stores on the Mag Mile, and every time I walk by they've changed the windows, and I'm like, I- now I need that. Sharon Pare: It's not window shopping anymore. Kristen Reynolds: Exactly. Sharon Pare: It's like, here's my plastic. Kristen Reynolds: That is it. And I'm also, I love the food. I'm a big foodie coming from New York. So the James Beard and Michelin star restaurants, to the mom and pop local restaurants that I love. So I [00:19:00] love to shop and I love to eat out. That's very Chicagoan of me, yes. Sharon Pare: It really is. It's not me- And so my last question then is deep dish. Kristen Reynolds: Yeah. Sharon Pare: Overrated, underrated? Kristen Reynolds: It's funny, 'cause before I moved there, being a New York pizza person- Sharon Pare: That's right ... Kristen Reynolds: I would have said overrated. But now I have it and I say definitely worth it on occasion. Ah. But here's an inside tip. Chicagoans will tell you tavern-style pizza. It's thin crust, it's over the edge. I've never heard that one before. This is some legit inside scoop. Like, that is Sharon Pare: super Kristen Reynolds: intel. Next time you go, tavern-style pizza is what, that's where it's at for the locals. Sharon Pare: Okay. Heard. Kristen Reynolds: There, we I know, we just, I just blew your mind. Sharon Pare: You blew my mind. Yeah. I had never even heard of tavern-style pizza. Kristen Reynolds: Yep, now you have to come back. Sharon Pare: AI wouldn't tell you that. You gotta talk to Kristen Reynolds about it. That's right. Exactly. Kristen, thank you so much. I mean, this was, has been amazing. I've learned so much about Chicago today. I've always loved the city. Now I wanna go back, and guess what? I'm gonna be back in October, so I might hit you up and Kristen Reynolds: get some of this intel. I'm gonna, I'm gonna grab you. We'll go get some tavern-style pizza. Sharon Pare: I, yes. Okay. And that's what we're gonna do. So thank you so much, and thanks to [00:20:00] everyone for listening to this podcast of Associations NOW Presents: Industry Partners Series. Please make sure to join us each month as we explore key topics relevant to association professionals, discuss the challenges and opportunities in the field today, and highlight the significant impact associations have on the economy, the US, and the world. We want to give a big thanks to our episode sponsors, Choose Chicago, and be sure to subscribe to our podcast on Apple, Spotify, or wherever you listen to your favorite podcasts.


















