Whether piloting new paths for Chicago’s cultural institutions or exploring the Arctic by kayak, Lynn Osmond embraces adventure. Born and raised in Ontario, she plunged into aquatic activities in her youth, including speed swimming, synchronized swimming, water polo, and rowing. She came to the Windy City when the Chicago Architecture Center recruited her to helm the org in 1996. This past May, she stepped down to become the first woman to lead Choose Chicago, the city’s official tourism advocate. Despite long hours on the job, the hydrophilic exec finds plenty of ways to stay active, including Sunday classes at Row House and swimming on the roof of Soho House. She makes a splash in Lake Michigan, too, typically while playing with Lester, her husky-terrier mix, at the Montrose Dog Beach.

Pickleball paddle and a salad
Photography: (paddle, salad) Getty Images

What’s your personal wellness philosophy?

“I’m not a fitness fanatic. Fitness just has to be a part of your daily regime. That includes a healthy diet and trying to get enough sleep. I’m an avid urban biker. I love to ride through the city and explore the neighborhoods — always with a destination for food somewhere attached. Sometimes I end up at Pan Artesanal on Fullerton. You don’t know nirvana until you try their chile relleno croissant.”

Do you have a favorite exercise?

“It’s a tossup between rowing and swimming. There’s nothing better in the world than being in the pool on a bright summer morning, swimming before the city’s really awake.”

How has your fitness routine shifted over time?

“The big one is adding Pilates to my workout. I really love it. I used to run, but now the knees don’t like that. I used to kayak a lot, too. I actually kayaked the Arctic with friends for over two weeks in 1998. It was weird and wonderful. We camped out and caught fresh Arctic char. Just six of us, a dog, and a gun. When you’re kayaking and see a polar bear coming towards you, it’s like, Ohhh shit. It’s amazing how fast you can paddle when you need to! Whenever I can in the summer, I still get out and kayak — in lake country in Canada or one of the boathouses in town, such as Ping Tom Park.”

What trendy workouts have you dabbled in?

“Well, I tried pickleball and did a face plant. I ended up starting my new job with four stitches in my face.”