Travel Smarter: B-Side Destinations, Route 66 Dreams, and the Best Travel Advice from the Chicago Travel & Adventure Show

Travel Inspiration from the Chicago Travel & Adventure Show

We attended the Chicago Travel & Adventure Show and heard from some of the most respected voices in travel. Here are the ideas that stuck with us.

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Seek Out “B-Side” Destinations

Travel expert Samantha Brown encouraged travelers to look beyond Europe’s most famous cities.

Instead of only visiting places like Venice or Florence, consider nearby destinations that offer incredible culture with fewer crowds—like Bologna or Modena in Italy.

These “B-side” cities often deliver deeper, more authentic travel experiences.

Is Route 66 the Most Iconic American Road Trip?

With the 100th anniversary of Route 66 in 2026, several speakers highlighted it as one of the most meaningful road trips in the United States.

Rather than rushing from Chicago to Santa Monica, consider tackling the route in segments and exploring the small towns and stories along the way.

Travel Like a Local

Travel writer Jen Ruiz shared how her travels changed when she started staying with local families.

Homestays and local connections can transform a trip from sightseeing into cultural immersion—offering experiences that are nearly impossible to replicate in traditional hotels.

A Simple Way to Give Back While Traveling

One initiative we learned about was Pack for a Purpose, which allows travelers to bring requested supplies to communities they visit.

It’s a small way to create a positive impact while traveling.

 

Smart Travel Planning Tips

Pauline Frommer shared several practical strategies that can help travelers save money and plan smarter.

When to Book Flights

According to their research:

• Domestic flights: best booked 15–30 days in advance
• International flights: best booked 31–45 days in advance

That timing can sometimes save travelers hundreds compared to booking many months in advance.

Gateway Hopping

Another strategy is flying into a major hub city and then connecting onward on a budget airline.

For example:

• Fly to major gateways like New York, Barcelona, London, or Paris
• Then book a short flight to your final destination

This approach can dramatically reduce airfare costs.

 

Chicago Highlights from the Trip

A Classic Chicago Steakhouse

One of our favorite experiences was dinner at Gene & Georgetti, a legendary Chicago steakhouse known for its old-school atmosphere and incredible steaks.

If you love classic steakhouses, this one is worth the splurge.

Chicago Deep Dish Pizza

We continued our unofficial mission to try Chicago’s most famous deep-dish pizza spots.

This trip’s stop: Lou Malnati’s, a Chicago favorite known for its buttery crust.

A World-Class Tiki Bar

We also returned to Three Dots and a Dash, one of the most famous tiki bars in the world.

If you visit, make a reservation—this place fills up fast.

 

Key Takeaways

Some of our biggest travel lessons from the show:

• Look beyond famous destinations for richer travel experiences
• Some of the best travel ideas come from conversations with other travelers
• You don’t always need to travel farther—just travel smarter