The Ultimate Route 66 Road Trip: One Week from Chicago to Santa Fe

For nearly a century, Route 66 has represented freedom, wanderlust, and the open road.

Stretching from Chicago to Santa Monica, this legendary highway has captured the imagination of generations of travelers.

Today, much of the route remains drivable, offering a nostalgic blend of Americana, neon signs, and small-town charm.

If you only have a week, a seven-day road trip from Chicago to Santa Fe lets you experience some of the most iconic—and scenic—stretches of the Mother Road without rushing the magic.

So, buckle up, grab your playlist of road trip classics, and get ready to follow that famous shield west through the heart of America. You’ll find vintage diners, quirky roadside attractions, and plenty of open skies waiting for you.

Day 1: Chicago, Illinois – Pontiac, Illinois (Approx. 100 miles)

Start where it all begins—at the official Route 66 “Begin” sign in downtown Chicago. Take a photo, because this is history in motion. Then, as you ease out of the city, stop for breakfast at Lou Mitchell’s, a classic diner that’s been serving Route 66 travelers since the 1920s.

Once you’ve left the urban bustle behind, the landscape quickly turns to fields and farm towns. Make a stop in Joliet for the Route 66 Welcome Center and the Rialto Square Theatre, then roll through Wilmington and Dwight, where restored gas stations and diners give off that old-time vibe.

Your destination for the night is Pontiac, a charming town with one of the best Route 66 museums around. Don’t miss the giant Route 66 mural for that perfect photo op.

Overnight: Pontiac, IL

Don’t Miss:

The Route 66 Hall of Fame and Museum in Pontiac – packed with vintage cars and nostalgic memorabilia.
The Pontiac-Oakland Automobile Museum for car lovers.
A stop at The Gemini Giant in Wilmington—a towering green spaceman watching over the Launching Pad Drive-In.
Grab a slice of pie at Old Log Cabin Restaurant, a Route 66 staple since the 1920s.

Day 2: Pontiac – St. Louis, Missouri (Approx. 180 miles)

Continue south through Illinois farmland toward St. Louis. Stop in Atlanta, IL, to see the world’s tallest “muffler man” holding a giant hot dog—a true Route 66 photo stop. Springfield, the capital city, is your halfway point today and is packed with Abraham Lincoln history.

Visit the Abraham Lincoln Presidential Library and Museum, or grab a cozy lunch at Cozy Dog Drive-In, the birthplace of the corn dog. From there, follow the old highway through Litchfield, home of the Ariston Café, one of the oldest restaurants on Route 66.

End your day crossing the Chain of Rocks Bridge into St. Louis, where the Gateway Arch rises like a shining welcome sign to the West.

Overnight: St. Louis, MO

Route Tips:

Visit the Route 66 Association Hall of Fame displays in McLean County along the way.
Stop in Lincoln, IL—the only city named for Abraham Lincoln before he became president.
Take time to explore Litchfield Museum and Route 66 Welcome Center—it’s small but charming.
In St. Louis, try local favorites like toasted ravioli or gooey butter cake.

Day 3: St. Louis – Springfield, Missouri (Approx. 215 miles)

Today you’ll wind your way through the rolling hills of the Missouri Ozarks. Route 66 in this state is one of the prettiest sections, with stretches of original pavement still visible.

Stop in Cuba, Missouri, nicknamed “Route 66 Mural City,” to check out its colorful outdoor artwork. Then cruise through Devil’s Elbow, a historic bridge and scenic bend in the Big Piney River that feels like stepping back in time.

When you reach Springfield, Missouri, you’ll find yourself in what’s often called the “Birthplace of Route 66”—the name was first proposed here in 1926. Don’t miss the Route 66 Car Museum or the retro Steak ‘n Shake, a perfect dinner stop.

Overnight: Springfield, MO

Don’t Miss:

Grab a bite at Missouri Hick Bar-B-Q in Cuba—it’s smoky perfection.
Take a short hike at Meramec Caverns, Jesse James’ legendary hideout.
Stop at Route 66 Rocker in Fanning—the world’s second-largest rocking chair.
Visit the Birthplace of Route 66 Roadside Park in Springfield for vintage signage and a great photo.

Day 4: Springfield, Missouri – Tulsa, Oklahoma (Approx. 180 miles)

You’ll say goodbye to Missouri today and cross into the land of red dirt and big skies—Oklahoma. The route from Joplin to Tulsa is rich with nostalgia, passing through small towns where time seems to have slowed down just for travelers like you.

In Carthage, stop at the 66 Drive-In Theatre, one of the few still operating on the route. Then check out the Route 66 Vintage Iron Motorcycle Museum in Miami, Oklahoma (My-am-uh).

Tulsa is your destination tonight, a lively city where Route 66 culture blends with art deco architecture and a growing food scene. Grab dinner downtown and take a nighttime stroll to see the neon-lit Blue Dome District—a modern nod to Route 66’s glowing past.

Overnight: Tulsa, OK

Route Tips:

Stop for photos at the Route 66 Mural Park in Joplin before leaving Missouri.
Visit Totem Pole Park in Foyil, OK—home to one of the world’s largest handmade totem poles.
Check out the Will Rogers Memorial Museum in Claremore for a slice of Oklahoma history.
Try Burn Co. BBQ or Mother Road Market in Tulsa for dinner—both local favorites.

Day 5: Tulsa – Oklahoma City, Oklahoma (Approx. 115 miles)

This is a shorter driving day, so you can take your time. Between Tulsa and Oklahoma City, Route 66 meanders through charming small towns that are proud of their Mother Road heritage.

Stop at Arcadia’s Round Barn, one of the most photographed landmarks on Route 66. Right down the road, POPS 66 Soda Ranch beckons with its massive neon soda bottle and hundreds of unique drink flavors inside—perfect for a midmorning sugar fix.

Once in Oklahoma City, visit the National Cowboy & Western Heritage Museum or stroll through the Bricktown Entertainment District for dinner and live music. Oklahoma’s section of Route 66 is one of the best preserved, and by now, you’ll see why locals love to keep it that way.

Overnight: Oklahoma City, OK

Don’t Miss:

Snap a selfie with the Giant Pop Bottle at POPS—especially at night when it glows.
Tour the quirky Seaba Station Motorcycle Museum in Warwick.
Grab a meal at The Rock Café in Stroud—featured in Pixar’s Cars.
Visit the Oklahoma Route 66 Museum in Clinton if you have extra time—it’s one of the best on the route.

Day 6: Oklahoma City – Amarillo, Texas (Approx. 260 miles)

It’s a long drive today, but the scenery makes up for it. You’ll cruise through wide-open plains, passing through classic small towns like Elk City, home to the National Route 66 Museum Complex.

As you cross into the Texas Panhandle, stop in Shamrock to see the beautifully restored U-Drop Inn, a 1930s art deco gas station that now serves as a visitor center and coffee shop. It’s a Route 66 icon that even made an appearance in Pixar’s Cars!

Roll into Amarillo by late afternoon and make your way to the famous Cadillac Ranch—a surreal art installation of half-buried, graffiti-covered cars rising from the dirt. Bring a can of spray paint and leave your mark!

End the day with a hearty Texas steak dinner at The Big Texan Steak Ranch, where brave souls attempt to finish a 72-ounce steak in one sitting. Even if you’re not up for the challenge, it’s worth watching someone else try!

Overnight: Amarillo, TX

Travel Tips:

Don’t miss the Tower Station & U-Drop Inn in Shamrock—especially at sunset.
Stop in McLean, TX, to see the Devil’s Rope Museum (barbed wire has a wild history).
Visit the Route 66 Historic District in Amarillo for antique shops and murals.
Bring old shoes for Cadillac Ranch—the ground gets muddy after rain!

Day 7: Amarillo, Texas – Santa Fe, New Mexico (Approx. 285 miles)

Your final stretch takes you west through the high plains into the enchanting landscapes of New Mexico. Stop in Tucumcari, where vintage motels like the Blue Swallow Inn still glow with neon after dark. It’s one of the most photogenic Route 66 towns still standing.

As you continue, the landscape shifts—flat farmland gives way to mesas, desert hues, and that distinct Southwestern vibe. In Santa Rosa, check out the Route 66 Auto Museum, then follow the winding route toward Santa Fe, one of America’s oldest and most artistic cities.

Santa Fe wasn’t part of the original Route 66 alignment after 1938, but it remains a favorite stop for travelers who want a mix of culture, food, and desert beauty. Stroll through the historic Plaza, explore local galleries, and toast your journey with a margarita as the sun sets over the Sangre de Cristo Mountains.

Overnight: Santa Fe, NM

Don’t Miss:

Stop in Adrian, TX, the “Midpoint of Route 66”—1,139 miles from both Chicago and L.A.
Grab a milkshake at Midpoint Café, a Route 66 institution.
Visit Blue Hole in Santa Rosa—a striking turquoise spring perfect for a quick dip or photo.
Try New Mexican cuisine in Santa Fe—enchiladas with green chile sauce are a must.

Tips for the Road

Plan flexible days. Route 66 is full of unexpected finds—vintage motels, antique stores, and roadside art you’ll want to explore.
Bring cash. Some small-town diners and mom-and-pop shops still don’t take cards.
Take the old alignments. GPS might steer you to the interstate, but the real Route 66 magic is on those slower, curvier roads.
Capture the moments. Every stretch of Route 66 has its own character, from neon-lit motels to lonely stretches framed by open sky.
Book motels early. Iconic stops like the Blue Swallow or Wigwam Motel can sell out in summer.
Travel at a slower pace. Half the fun is the nostalgia—don’t rush it.

Wrapping Up Your Journey

After seven unforgettable days, you’ll have crossed five states, countless landmarks, and nearly a thousand miles of American nostalgia. From Chicago’s skyline to the sun-baked mesas of New Mexico, Route 66 offers something timeless—a reminder that the journey itself is what matters most.

So, what do you think? Ready to roll down the windows, cue up some Chuck Berry, and chase that endless horizon? Because the Mother Road is waiting, and she never disappoints.