Focus on authenticity: In the post-COVID world, travelers are looking for authentic experiences more than ever before. Destinations must deliver an authentic experience that allows travelers to live like a local while they are here.

As part of my series about “How To Create A Travel Experience That Keeps People Coming Back For More”, I had the pleasure of interviewing Lynn Osmond of Choose Chicago.

As President and CEO of Choose Chicago, Lynn leads the official sales and marketing organization of Chicago and serves as the voice of the city’s tourism industry. She is tasked with bringing regional, national, and international business and leisure visitors to Chicago for the economic benefit of the city and its residents.
Prior to joining Choose Chicago, Lynn led the Chicago Architecture Center, (CAC), formerly the Chicago Architecture Foundation, through fundamental transformations for 25 years, expanding the mission from being focused on architecture enthusiasts to educating the general public about Why Design Matters. 
She is passionate about Chicago and believes wholeheartedly in the power of travel to transform communities.

Thank you so much for joining us! Can you tell us a story about what brought you to this specific career path?

While I’ve been a proud Chicagoan for more than two decades, my journey to Chicago’s tourism and hospitality industry began in an unexpected location — Canada. Originally from Ontario, I was recruited over 25 years ago to lead the Chicago Architecture Center, which runs Chicago’s world-famous Architecture River Cruise. Chicago very quickly felt like home, and I was always felt like a local. It was during that time that I wanted to become more immersed with the community and sat on the Board of Choose Chicago and served as Vice Chair, as well as The Magnificent Mile Association.

I am passionate about Chicago and understand the importance of tourism to our community as a key economic driver, so it was a natural fit for me to lead Choose Chicago, and I’m very honored to be the first woman President and CEO of the organization.

Can you share the most interesting story that happened to you since you started your career?

In this industry, I’ve been very grateful to have been a part of many creative and interesting experiences to promote our City. However, the most exciting and unexpected opportunities happened more recently when I joined our Mayor and Governor to pitch the Democratic National Committee (DNC) convention to Chicago. Growing up in Canada, I would never have imagined dipping a toe in American politics and selling Chicago to this high-powered group.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

Because Chicago has a variety of hotels, food scenes, green spaces and other attractions, we hosts many corporate meetings and trade shows every year. One of my first major events as President and CEO of Choose Chicago was the National Restaurant Show in 2022, a huge annual tradeshow at McCormick Place, Chicago’s convention center. I made the huge mistake of wearing high heels to the opening of the show, which uses nearly all the 2.6 million square feet of exhibition space at the convention center. After I could feel my feet again, I learned to wear my McCormick Place shoes when touring shows and keep my heels in my office!

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

I am grateful to my husband. I remember when we were dating I told him about what had happened at a meeting where one of the men in the room was trying to steamroll over me. He told me to stop feeling sorry and to stand up for myself. This was tough love, but it was true, and those words have stayed with me as I have built my career.

Can you share with our readers about the innovations that you are bringing to the travel and hospitality industries?

I have what I call “a new set of glasses” that I use to see the industry, with a particular focus on our neighborhoods and the residents that make Chicago so unique. As a longtime resident of Chicago and someone that led a tourist attraction for 25 years, I have developed a deep passion for the city and our neighborhoods and Chicago has 77 of them! I know that the visitor is looking for an authentic tourism experience, which is why I am focusing on building our neighborhoods so that we can offer experiences that visitors want while also making tourism equitable for all of Chicago’s residents.

Which “pain point” are you trying to address by introducing this innovation and how do you envision that this might disrupt the status quo?

Destination marketing organizations like Choose Chicago have historically focused on the visitor that comes in rather than the residents of their city. I think we have to do more to get our residents involved in the narrative of the city and to encourage them to become tourists in their own town. As the capital of the Midwest, friends and family are a key market sector for Chicago. By engaging residents and highlighting our neighborhoods, we are building ambassadors for our city and bringing awareness of the importance of tourism to our city and state.

As you know, COVID19 changed the world as we know it. Can you share a few examples of how travel and hospitality companies will be adjusting over the next five years to the new ways that consumers will prefer to travel?

There is no doubt that the COVID-19 pandemic has forever changed the world of travel. While we are excited to share that 2022 was a successful year of recovery in Chicago, we are still facing a new reality and we do not expect the industry to simply return to how it was prior to the pandemic.

One major trend we are seeing is that, more than ever before, visitors are looking for authenticity in their travel. COVID forced people to stop traveling, and now that it is available once again it is not enough to simply “get away” for a trip. Tourists want to be more than merely tourists and are seeking meaningful experiences that allow them to understand what it’s like to be a local. As a destination marketing organization, we are watching this trend closely and focusing on promoting our neighborhoods and the authentic experiences that make Chicago unique.

We are also seeing a renewed focus on visitors from the Midwest. Given all of the ongoing uncertainty related to travel and the economy, more and more people are planning vacations to destinations that are within driving distance. For us, that means we need to focus our marketing efforts to a greater extent on the regional market, such as the Chicago suburbs and neighboring states.

Finally, another major trend we have seen over the last few years is the rise of TikTok as the source of travel inspiration. According to MMGY Global, about 34 percent of travelers were influenced by TikTok in 2022, a 10 percentage point increase over 2021. To market Chicago we must be present on TikTok, which is why we work closely with social media influencers and just launched our own TikTok channel last year.

You are a “travel insider”. How would you describe your “perfect vacation experience”?

I believe perfect vacations should have a mix of relaxing and exciting experiences. I recently traveled to Portugal and had my dream travel experience. It was a wonderful combination of everything you want in a vacation — from urban and culinary experiences, to touring the countryside. Giving people a mix of relaxing and exciting experiences is something I cherished on this trip and something we strive to give everyone who visits Chicago as well.

Travel is not always about escaping, but about connecting. Have you made efforts to cultivate a more wellness driven experience? We’d love to hear about it.

Staying active is very important to me for wellness. I have always participated in water sports even growing up and now make time for swimming or taking my dog to the local dog beach. I’m also an avid urban biker. I love to ride through the city and explore the neighborhoods — end up at a fabulous food destination.

Now more of a tradition, but every year I go to Cape May Point, NJ where I clear my head and rejuvenate my soul by just walking the beach, smelling the sea air and reconnecting with my husband. This is an important time for me every year to recalibrate and invigorate myself.

Based on your experience and success, what are the five most important things one should know in order to create a travel experience that keeps bringing people back for more? Please share a story or an example for each.

Have a variety of experiences: Tourists look for so many different things on their vacations. To be a successful destination you must offer a variety of different experiences to appeal to all types of visitors. Here in Chicago we do a very good job offering a variety of experiences, from world-class cultural institutions to outdoor activities to iconic sporting events to amazing restaurants and entertainment.

Strong customer service: To be a great destination, you need to make your visitors feel welcome. Chicago consistently lauded for its incredible hospitality community that goes above and beyond to make a friendly environment for tourists. We are “Midwest-nice” and love showing off our city to visitors.

Exceed expectations: To make people keep coming back for more, you need to deliver a tourist experience that is better than expectations. In Chicago, we are so much more than what you may read in the news, which is why we constantly hear that visitors are blown away by their time in Chicago. A prime example of this is our architecture — we have an iconic skyline and beautiful neighborhood architecture that keeps people wanting to explore more.

Keep adapting: The last three years have taught us all that to be a successful destination you must be ready and willing to adapt to the changing world. This means being able to offer a COVID-safe tourist experience, especially during the worst of the pandemic, while also adapting to the post-COVID traveler.

Focus on authenticity: In the post-COVID world, travelers are looking for authentic experiences more than ever before. Destinations must deliver an authentic experience that allows travelers to live like a local while they are here.

Can you share with our readers how you have used your success to bring goodness to the world?

I am a firm believer in the positive impact of tourism on a destination and its people. In 2022, visitors to Chicago pumped $17 billion into our local economy. That money directly supports thousands of small businesses and hundreds of thousands of workers, and also provided much-needed tax dollars to support critical services to our city.

As the head of the City’s tourism agency, any success that I have directly translates to success for our city and its residents. The better I do my job, the stronger we are as a city.

At this and my previous role as head of the Chicago Architecture Center, I hope that I have brought goodness to all Chicagoans by eliciting pride in our city and driving more and more visitors here for the economic benefit of all our residents.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be?

If I could start a movement it would be to drive more people to visit and experience diverse communities, both in Chicago and around the world. I think if everyone went out of their way to visit different and diverse communities, it would lead to a great understanding between communities and more sharing of resources to make our global community a better place to live. In Chicago, we are a city of diverse and unique neighborhoods, but it is all too easy to isolate yourself and miss out on the richness that is only available when you get out of your comfort zone and experience a culture different than your own.

How can our readers follow you on social media?


Twitter: @losmond

LinkedIn: Lynn Osmond


Twitter: @choosechicago

Facebook: ChooseChicago

Instagram: @choosechicago

TikTok: @choosechicago

LinkedIn: Choose Chicago

This was very inspiring. Thank you so much for joining us!


  • Savio Clemente

    Board Certified Wellness Coach (NBC-HWC, ACC), Media Journalist, #1 Best-selling Author, Podcaster, and Stage 3 Cancer Survivor

    The Human Resolve LLC

    Savio P. Clemente is a Board Certified Wellness Coach (NBC-HWC, ACC), media journalist, #1 best-selling author, podcaster, stage 3 cancer survivor, and founder of The Human Resolve LLCHe coaches cancer survivors and ambitious industry leaders to amplify their impact, attract media attention, and make their voice heard. He inspires them to get busy living in mind, body, and spirit and to cultivate resilience in their mindset.

    Savio has interviewed notable celebrities and TV personalities and has been invited to cover numerous industry events throughout the U.S. and abroad.  His mission is to provide clients, listeners, and viewers alike with tangible takeaways on how to lead a truly healthy, wealthy, and wise lifestyle.