Every winter, just when Michigan’s grey starts to feel truly relentless, we make our annual pilgrimage to Chicago for the Travel & Adventure Show. This was our fourth year at the travel show, and as always, it delivered — inspiration, great food, and a renewed itch to book something.
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The Speakers
The undeniable highlight was Samantha Brown, making her case for “B-side cities.” With overtourism increasingly affecting Europe’s big names, she encouraged the audience to look beyond the obvious and dig into places like Bologna and Modena, which she called “the B-side of the B-side.” — which she covered in two episodes of her current season of Places to Love — If you’ve read our Italy posts or listened to the podcast, you know we’re already converts. We went home, watched her episodes, and immediately started talking about going back.
She also made a passionate case for Route 66, fitting since 2026 marks its 100th anniversary. She recommended the EZ66 Guide for navigating the patchwork of surviving roads and described it as possibly the most important road trip in America. It’s officially on our list.
Pauline Frommer offered her reliably practical perspective, echoing the B-side-cities theme and sharing some genuinely useful airfare data: for domestic travel, booking 15-30 days out saves an average of $130 versus six months ahead; for international, 31-45 days saves around $190. She also recommended Momondo for flight searches, and made a compelling case for gateway hopping — routing through major hub cities rather than hunting for direct flights from smaller airports. We’d just done exactly this for an upcoming trip to Spain, routing through New York and Barcelona for around $300 per person round trip. Hard to argue with.
Our sleeper favorite of the weekend was Jen Ruiz of Jen on a Jet Plane — a former lawyer who set a goal of 12 trips in 12 months, ended up doing 20, and never looked back. Her talk on traveling like a local was full of energy and genuinely changed how we think about immersive travel. She also introduced us to Pack for a Purpose, a service that lets you look up your destination before you go and see what donated items local communities need. Simple, meaningful, and now part of how we plan to pack.
Chicago Itself
We stayed in River North, as always, and ate extremely well. Gene & Georgetti — an old-school Italian-American steakhouse featured in the cookbook Steakhouse — was the meal of the trip. The garbage salad (topped with shrimp, which we did not expect), the bread, and a bone-in ribeye that was worth every penny. Book a reservation at least a month out.
We also finally made it to Lou Malnati’s to continue our quest through Chicago’s deep dish institutions — best of the bunch so far — and ended the trip at Three Dots and a Dash, one of the country’s great tiki bars. Next time we’ll make a reservation there too.
Have you been to the Travel & Adventure Show? We’d love to hear about it in the comments.
Thanks for stopping by! Check out our Go See Do Explore Podcast, available wherever you listen to podcasts. To read about some of our previous trips, visit my Trips Page. If you like my photos be sure to “like” my Facebook Page and follow me on Instagram! For my list of gadgets to make your travels easier, click here.