Day 1: Touch down in Chicago
For your first day of the trip, fly into one of Chicago’s airports: either Chicago O’Hare and Chicago Midway. From there, spend some time exploring the city and perhaps catch up on America’s favorite pastime at the famous Wrigley Field.
Take the day to see some of the city’s landmarks, including the Field Museum of Natural History (admission starts at $22 for adults). Make sure to visit the symbolic starting point of Route 66: the Art Institute of Chicago in Grant Park. (Chicago's last official US-66 sign used to hang from a streetlight just south of the gallery.) While you’re in the area, drive down Jackson Boulevard and grab coffee at Lou Mitchell’s diner. It’s a Chicago institution and part of Route 66 lore.
Day 3: Chicago to St. Louis
Drivers, start your engines: You’ll be driving about 300 miles south toward St. Louis today. Stop in Pontiac, Ill., to visit the Route 66 Association Hall of Fame & Museum (admission by donation), where you’ll find thousands of pieces of memorabilia commemorating the famous trek. If you’d prefer to stay outside St. Louis, bunk up at the famous Munger Moss Motel in Lebanon, Missouri.
Spend the day taking in the sights and sounds of St. Louis. Check out the city’s iconic Gateway Arch, and go all the way to the top ($13 for adults). Make time to tour the year-old National Blues Museum ($15 for adults), which features dozens of interactive exhibits and artifacts that explore the history and regional variations of the blues. End the night on a sweet note with a treat from Ted Drewes Frozen Custard.
Day 5: St. Louis to Tulsa
As you drive southwest out of St. Louis, take a detour to the famous Meramec Caverns ($21 for cave tour), where legend has it that outlaw Jesse James made his hideout in the 1800s. And before you wrap up your day's drive, stop for a photo of the Blue Whale of Catoosa, a 80-foot-long statue that’s been entertaining visitors since the 1970s. Once in Tulsa, unwind with a movie at the Admiral Twin Drive-In ($7 for adults), a classic drive-in cinema that was featured in S. E. Hinton’s novel The Outsiders. Unwind for the night at the Campbell Hotel, a boutique hotel located directly on Route 66.
Day 6: Tulsa to Oklahoma City
On the drive into Oklahoma City, stop at the iconic Pops in Arcadia. The old-fashioned soda shop has 700 flavored beverages, and serves them up alongside a 66-foot-tall neon soda bottle. Once you arrive in town, get to know Oklahoma City’s roots with a visit to Stockyard City, a former public livestock market built in the 1900s; it's since been turned into Western-themed shopping and dining. Downtown is also home to the Oklahoma City National Memorial and museum ($15 for adults), built to commemorate the victims and survivors of the 1995 bombing.
Day 7: Oklahoma City to Amarillo, Texas
It’s on to Texas today, for a quick crossing of the Panhandle. Start by driving 185 miles to McLean, Texas, and visiting the Devil’s Rope Museum (free admission). At this kitschy stop, you’ll learn all about the history, use and varieties of barbed wire. Then continue on to Amarillo, where you'll spend the night. Just outside the town limits sits the Instagram-worthy Cadillac Ranch, a 1970s public art installation featuring 10 decorated Cadillacs standing upright. You can also check out the Jack Sisemore Traveland RV Museum, filled dozens of vintage RVs.
Day 8: Amarillo to Albuquerque
Before saying goodbye to Texas, make a pit stop in Adrian — the halfway point between Chicago and Los Angeles. Then cruise through Tucumcari, New Mexico, on your way to Albuquerque. This stretch is the “best-preserved” portion of Route 66, Godt says, with campy stopovers and shops like Tee Pee Curios, Godt says.
Get out of the car and spend the day exploring Albuquerque (named one of MONEY’s top U.S. destinations to visit in 2017). Visit the Indian Pueblo Cultural Center ($8 for adults) and take in the gorgeous desert scenery from the Sandia Peak Tramway ($25 for adults). Albuquerque is also home to the Petroglyph National Monument, a 17-mile trail filled with volcanic rocks that have etchings and symbols carved by Native Americans and early Spanish settlers. Grab dinner at Kellys Brew Pub, which serves 20 house-made beers.
Day 10: Albuquerque to Flagstaff, Arizona
About an hour outside of Albuquerque lies the Acoma Pueblo, the oldest continuously inhabited community in the U.S. Stop for a short visit here, then drive on to Flagstaff, Arizona, and wander the town's eclectic, pedestrian-friendly downtown. Check out local eateries such as Diablo Burger where the signature sandwich is served on a English muffin that's been seared with the restaurant logo ($11-$13). In the evening, visit the famous Lowell Observatory ($15 for adults), where scientists discovered Pluto in 1930.
Make Flagstaff your base as you gear up for a day outdoors. “It’s good to get out and see some of the natural wonders,” Godt says. Hit the trails at Red Rock State Park ($7 for adults) in nearby Sedona, where you can view the breathtaking red sandstone canyon. There's also the nearby the Coconino National Forest, home to the famous Ponderosa pines. Or stay closer to town and visit Walnut Canyon National Monument ($8 for adults) to see the ancient Sinagua cliff dwellings.
Day 12: Flagstaff to Barstow, California
Put Flagstaff in the rearview mirror and head west toward California. Stop for an early lunch at Delgadillo's Snow Cap Drive-In, a classic Route 66 diner serving up food along with a side of humor in Seligman, Arizona. If you’re feeling adventurous, drive on toward the Mojave National Preserve’s visitor center, a converted train depot in Kelso, California. Spend the afternoon cruising around the Providence Mountains, where you’ll be able to see the famous Joshua trees. Bunk down for the night in nearby Barstow, a classic crossroads for desert travelers.
Day 14: Head home from L.A.
If you haven’t been to Los Angeles before, make sure to take a spin down Hollywood Boulevard before you depart. This is where you’ll find the Hollywood Walk of Fame; you might even have time to catch a movie at Grauman's Chinese Theatre. Then it’s wheels up as you head back home via Los Angeles International Airport.