Travel Guide: Route 66 Road Trip – Part 1

Lisa-Ng-Route 66-Road-Trip

Are you planning a Route 66 Road Trip?

As crazy as it sounds, Paul and I have driven Route 66 TWICE. Once for vacation and the second time for when we moved from Toronto to Los Angeles. I thought I would put together a round-up of my favourite stops for anyone thinking of doing their own Route 66 Road Trip.


Start Here! Your starting point will be at a Route 66 sign on the side of a busy road, just in front of the Art Institue of Chicago. You’ll have to put your four-ways on and be super quick! Make sure to grab a selfie here before you set off on your big Route 66 road trip.


Giant Gemini? Check! Eat a Chicago-style hot dog? Easy! Once you start making your way out of Chicago, you’ll pass a few fun landmarks and diners on your Route 66 road trip. Henry’s Drive-In is a great place to stop for a Chicago Dog in Cicero, IL. About an hour away in Wilmington, IL you’ll bump into this Gemini Giant in the parking lot of the now defunct diner.

If you haven’t already, download Road Trip 66, an app that shows you quirky restaurants, relics, signage and fun stops on a map along the way. It was super helpful for us to find a few hidden gems on our Route 66 road trip.


Did Someone Say Fried Chicken? Of course, we were trying to eat as healthy as much as possible. We made a stop at Dell Rhea’s Chicken Basket for their Fried Chicken Dinner in Willowbrook, Illinois – which was featured on Diners, Drive-ins and Dives. It used to be the site of an old Blue Bird bus stop and the chicken basket became famous along the route.


A must-stop on your Route 66 road trip is The Cozy Dog Drive-in, birthplace of the original hot dog on a stick aka corn dog. Who can seriously resist when they are only $1.95 each? We chatted with a local in Springfield, Illinois (we went through TWO Springfields in 48 hours, but no Shelbyville?) and he’s been going to this Route 66 institution since he was a kid.

Ice Cream Stand

First off, we have ourselves a case of ice cream cone inception. I am eating an ice cream cone dispensed by a person working inside an ice cream cone. Like woah. There’s just something about a soft-serve chocolate dipped cone that just SCREAMS summer. This retro Tastee Treat ice cream stand is outside of The Pink Elephant Antique Mall in Livingston, Illinois – near St. Louis. If you’re doing a Route 66 road trip, PLEASE make sure you stop in and look at all the random/vintage/retro stuff inside this old school building-turned-antique-mall.


The giant ice cream cone is not to be outdone. We came across The World’s Largest Catsup Bottle in Collinsville, Illinois. It’s an old water tower for the former Brooks Catsup factory. It even has its own website, fan club and twitter account.


One of the most surprising cities on my Route 66 road trip was St. Louis, Missouri! I had no expectations and barely did my research since we were blowing through this town for one night. Well, I fell for St. Louis after 24 hours and promised myself a longer visit the next time I returned. I wrote an in-depth post of what to eat, see and do in St. Louis for lots of road trip stop ideas that won’t fit into this post.


St. Louis Union Station – If you’re in the area, this majestic space is definitely worth a peek. The food court and mall attached to it was looking a bit sad, but there is a cute little ‘lake’ where you can rent pedal boats and glide along under the old station roof where trains used to come in. The Hilton Hotel inside the station is pretty too.


I hope I gave you a few ideas to get your wheels turning! Stay tuned for Part 2 of my Route 66 Road Trip Travel Guide, where I’ll pick up with trip ideas in Oklahoma and beyond! In the meantime, do check out my Travel Guide: St. Louis, Missouri for more  Route 66 road trip ideas.

Talk soon!


  • Matt Del Biondi

    Can’t wait for part 2!