The Ultimate Route 66 Road Trip: Chicago to Santa Monica
Route 66!
Stretching from Chicago to Santa Monica, this legendary highway is less about the destination and more about the stories you collect along the way.
Think vintage diners, desert skies, neon motels, and those quiet stretches where it’s just you, the music, and the horizon.
This is your WildHer-style guide to doing Route 66 right.
Stop 1: Chicago, Illinois — Where It Begins
Start where it all began. Snap your photo at the iconic Route 66 sign on Adams Street, then ease into the journey with a classic breakfast at Lou Mitchell's—a local staple that feels like stepping back in time.
WildHer Tip: Don’t rush out of Chicago. Walk along Lake Michigan, grab a coffee, and set your intention for the journey ahead.
Stop 2: St. Louis, Missouri — Gateway Energy
Roll into St. Louis and feel the shift—the Midwest giving way to something bigger. Walk beneath the Gateway Arch, then cross the historic Chain of Rocks Bridge for a true Route 66 moment.
Don’t miss: A stop at Ted Drewes Frozen Custard—order it “concrete style.”
Stop 3: Tulsa, Oklahoma — Retro Meets Revival
Tulsa is one of Route 66’s coolest surprises. Art deco architecture, neon lights, and a creative energy that feels alive.
Wander the Blue Dome District, hunt for vintage signs, and lean into the nostalgia.
Stop 4: Amarillo, Texas — Desert Playgrounds
Welcome to wide-open Texas skies. Outside Amarillo, you’ll find Cadillac Ranch—a surreal, ever-changing art installation where you can leave your mark.
Do it: Bring spray paint. Yes, really.
Stop 5: Santa Fe, New Mexico — Soulful Detour
While not on the original alignment, the detour to Santa Fe is worth every mile.
Adobe architecture, art galleries, desert air—it’s grounding and inspiring all at once.
WildHer moment: Book a spa, wander solo, journal somewhere quiet.
Stop 6: Flagstaff, Arizona — Mountains & Magic
Flagstaff brings a total shift in scenery—pine forests, crisp air, and a cozy mountain-town feel.
From here, you’re also close to one of the world’s wonders: Grand Canyon National Park.
Stop 7: Santa Monica, California — The Finish Line
You made it. The road ends at the Pacific Ocean in Santa Monica.
Stand by the “End of the Trail” sign on the pier, take a deep breath, and let it land—you just crossed the country.
How to Do Route 66 the WildHer Way
Give yourself 10–14 days
This isn’t a rushed trip. Build in time to wander.
Mix vintage with comfort
Stay in a few retro motels—but balance it with beautiful boutique stays.
Pack intentionally
Easy layers (desert to mountains = temperature swings)
A great playlist
A journal (trust me)
Travel solo or with your people
Route 66 is perfect for a solo reset, a girls’ trip, or even a mother-daughter adventure.
Planning Your Own Route 66 Adventure?
If you want help mapping out your stops, booking unique stays, that’s what we do!
