By Partner, Sean Beckingham

Between October 31 and January 7, I traveled across North America, hitting Vancouver, Winnipeg, Chicago, and Florida. Each stop was a mix of work, new connections, and memorable experiences.

This series will cover the highlights from each place, including learning about the alcohol industry in Vancouver, reconnecting with old friends in Winnipeg, eating hot dogs in Chicago, and building a business community in Florida.

 

Chicago: Hot Dogs, Baseball, and Perfect Work-Life Balance

Chicago is one of those cities we keep coming back to—this was our fourth visit. Every time, it’s the perfect mix of life and work.

On past trips, we’ve created content for the U.S. division of one of our clients and attended the NRA Show. Baseball has always been part of our time in Chicago, and this trip came with a mission: eat hot dogs everywhere. Years ago, while pitching a Jays vs. White Sox hot dog tasting campaign, we promised ourselves we’d try them all, even though the campaign never went anywhere. This time, we finally kept that promise.

As always, the food in Chicago didn’t disappoint. Like Toronto, you can find incredible eats everywhere. Special shout-out to  Seoul Tacos—definitely worth checking out. Plus Byron, our local hotdog.

 

During our stay in Wrigleyville, Chicago, we took our daily walks around Wrigleyville Park, neighborhood’s charming with its walkups and main streets. It was great to witness the setup for the Winter NHL Classic at Wrigley Field, watching the iconic stadium transform into a hockey arena… Our Airbnb was a classic walk-up, complete with a dedicated office space—an absolute must for work calls when you’re blending travel and business. FACT: we’ve now surpassed 50+ positive Airbnb stays, a testament to how seamlessly we balance work and exploration! You think they would send us a sticker or something.