Having driven America’s most iconic road some 75 times, Austin Coop has mastered a westward itinerary on Route 66 that features everything you’d expect — “the mom-and-pop places, the old gas stations, the old motels” — but also hidden gems, such as lunch on the stage of a historic theater in Miami, Oklahoma, and a St. Louis glass mosaic that’s the largest outside of Russia. You’ll hear from your guide at planned stops on the 2,400-mile journey from Chicago to the Santa Monica Pier, as well as on a walkie-talkie he provides to all 15 vehicles in the caravan. As for lodging, don’t worry — you won’t be sleeping in your car. Think Holiday Inn Express.

About the guide: After working soul-draining corporate jobs in his mid-20s, Coop stumbled on a Craigslist employment ad that posed a simple question: “Do you like road trips?” It was a listing from Roadtrippers, which hired Coop as a guide focused on Route 66. But the Ukrainian Village resident soon noticed that while loads of companies offered bus excursions of the Mother Road, no guided tour allowed you to drive your own car. That inspired Coop to found his own tour company, Two Lane America, in 2015.

Bring: Your voice for car karaoke. Coop shares a Spotify playlist of jams for each day’s drive.

Watch for: A pitch-black sky. As you cross into California, you’ll pass the Mojave Trails National Monument, home to some of the darkest nights in the United States. It’s a two-and-a-half-hour round-trip detour, but worth it.

Route 66’s Local Pit Stops

Can’t commit to hitting the highway for two weeks? Here are Coop’s favorite places along the Mother Road, all within four hours of Chicago.

Paul Bunyan’s New Friends
long had just one big (literally) tourist draw: a 19-foot-tall statue of Paul Bunyan holding an oversize hot dog that used to tower over Bunyan’s, a now-shuttered Cicero drive-in. “A couple of guys had the bright idea that everybody loves these giant statues,” Coop says. “They said, ‘What if we tried to get more of them?’ ” The one-block town is now home to the American Giants Museum, which preserves the few remaining Muffler Men — giant fiberglass statues that once lined Route 66 to attract attention to roadside restaurants and stores. Arch and Vine Streets, Atlanta

Cozy Dog Drive In
You don’t even need to get out of your car. Just pull right up for a Cozy Dog, the original corn dog on a stick, first served at the Illinois State Fair in 1946. Tip: Order cheese on a stick for your side. 2935 S. Sixth St., Springfield

Old-School Gas Stations
For a true old-school at-the-pump experience, you can find what Coop calls “three of the very best” old gas stations: Ambler’s Texaco in Dwight (417 W. Waupansie St.), Soulsby’s in Mount Olive (710 W. First St.), and the Standard in Odell (400 S. West St.).