From Chicago to the Pacific: The Ultimate Route 66 Adventure

Hosted by

Linus

7 Days30 Days!

Extra Cancellation Days
only for the first TripMate

Guided trip
What's special?
special 🚗 Classic American road trip
special 🌄 Desert, diners & neon nostalgia
special 🤠 Small towns & authentic Americana
“Get Your Kicks on Route 66” 🇺🇸 Route 66 Adventure Road Trip – 15 Days from Chicago to Santa Monica Ready for the ultimate American road trip? 🌵✨ We’ll cruise the legendary Route 66 from Chicago to Santa Monica, crossing 8 states, 4 time zones, and over 3,900 kilometers of pure freedom. From neon-lit diners and wild desert landscapes to quirky roadside stops and national parks — this journey is all about adventure, nostalgia, and good vibes. We’ll start in the buzzing streets of Chicago, then roll through small-town America, the red rocks of New Mexico, the canyons of Arizona, and finish with our feet in the Pacific Ocean at Santa Monica Pier 🌅. Along the way, we’ll explore caves, deserts, vintage motels, and famous landmarks — all while making stops for short hikes, local eats, and amazing photo ops. Expect sunsets over the Grand Canyon, Route 66 murals glowing at night, and the simple joy of driving through endless open roads with good music and great people 🎶🚗 This is not just a trip — it’s a piece of living history. Join a small crew of adventurers and let’s chase the classic American dream, one diner milkshake at a time 🥤🇺🇸 ⸻ ✨ What to Expect • 🚙 15 days / 8 states – from Chicago’s skyscrapers to California beaches • 🏜️ Mix of city vibes, nature stops, and hidden roadside gems • 🏕️ Motels & local diners for the real Route 66 feel • 🌄 Optional short hikes in Grand Canyon, Petrified Forest, and Mojave Desert • 🎶 Traditional Music and Honky Tonk Dancing Bars

Hey guys, I’m Linus, 26 years old and a passionate traveler at heart. Since graduating high school, I’ve been combining work and travel, exploring the world in many ways – from quick city getaways to month-long road trips, and even living and working in Australia, Canada, and the U.S. I’m all about nature and adventure: hiking, skiing, off-roading, swimming, and discovering new places with great people. As your TripLeader, I handle the planning, logistics, and organization so you can simply enjoy the experience. My trips are “everything included” (except flights and maybe a few drinks at night), because I know how stressful travel planning can be – especially if it’s your first time traveling solo. Safety, comfort, and good vibes are my top priorities. I make sure everything runs smoothly and that everyone feels welcome and included from day one. You can expect a relaxed atmosphere, good conversations, and plenty of laughs along the way. Can’t wait to share some of my favorite spots and create amazing memories together. Lets Discover the World Off-the-beaten-Path together! See you on our next adventure! 🌍

Get your kicks on Route 66! Join me for the ultimate American road trip — two weeks, eight states, and nearly 4 000 km of open road from Chicago’s skyline to the beaches of Santa Monica. We’ll cruise through historic towns, stay in retro motels, eat at classic diners, and explore incredible nature along the way. On top of that, we will be visiting some truly American Dive Bars where we will be enjoying some local drinks and listen to live music. Expect neon signs, desert drives, and hikes in national parks like the Grand Canyon, Petrified Forest, Palo Duro Canyon, and Mojave Desert.

What's included?
Full Size Rental Car including Gas
Accommodation
Breakfast
National Park & Attractions Entry Fees
Your Booking includes free protection from Trip cancellations.
Learn More
TripLeaders Personal Message
Meet Your TripLeader
Phone Verified
Identity Verified
38 Countries

Travel and nature lover with a soft spot for good food, great music, and guiding awesome trips

You can chat with Linus once you reserve your spot.
Trip Itinerary
1

Chicago

Day 1-2
Kick off your adventure where Route 66 was born! From Chicago’s skyscrapers to the open Illinois countryside, this day captures the transition from city life to small-town America. Enjoy diners, murals, and a taste of Americana on your first stretch. Stops on the way: • 📍 Route 66 “Begin” Sign & Lou Mitchell’s Diner • 🎨 Pontiac Route 66 Hall of Fame Museum • 🏡 Lincoln Home National Historic Site (short walk)
2

Springfield

Day 2-3
Cruise through rural Illinois into the lively heart of St Louis, crossing the mighty Mississippi River. Historic bridges, blues music, and the famous Gateway Arch await on the other side. Stops on the way: • 🌉 Chain of Rocks Bridge walk • 🏛️ Gateway Arch National Park • 🍦 Ted Drewes Frozen Custard
3

St. Louis

Day 3-4
Today brings caves, springs, and classic roadside attractions. You’ll travel scenic stretches of old Route 66 through forested Missouri hills and hidden natural wonders. Stops on the way: • 🧭 Meramec Caverns tour & trail • 💧 Maramec Spring Park walk • 🎨 Cuba MO murals & Route 66 Rocking Chair
4

Springfield

Day 4-5
Cross from the Ozarks into Oklahoma, with wide skies and rolling plains. Expect colorful small towns, retro movie theaters, and a giant smiling whale. Stops on the way: • 🎞️ 66 Drive-In Cinema (Carthage) • 🌿 Wildcat Park Trail (Joplin) • 🐋 Blue Whale of Catoosa
5

Tulsa

Day 5-6
The Sooner State offers classic Route 66 nostalgia mixed with red-rock canyons and quirky roadside icons. Enjoy a slower pace and true Midwestern charm. Stops on the way: • 🏜️ Red Rock Canyon State Park (hike) • 🛢️ Round Barn of Arcadia • 🥤 POPS 66 Soda Ranch
6

Oklahoma City

Day 6-7
Head into cowboy country! Today’s drive takes you through wide-open prairie, western heritage sites, and vibrant sunsets. Stops on the way: • 🏚️ Lucille’s Historic Gas Station • 🏞️ Washita Battlefield Trail • 🎨 Cadillac Ranch
7

Amarillo

Day 7-8
🌵 Day 7 – Amarillo → Tucumcari → Santa Rosa (NM) Leave Texas for New Mexico’s desert landscapes and vintage neon towns. The Mother Road turns magical under the big Southwestern sky. Stops on the way: • 🍔 Midpoint Café (halfway marker) • 🌄 Tucumcari Neon Row & Murals • 🚗 Route 66 Auto Museum (Santa Rosa)
8

Santa Rosa

Day 8-9
🏜️ Day 8 – Santa Rosa → Santa Fe → Albuquerque A day of culture and color — adobe towns, mountain roads, and endless views. Enjoy a blend of Native American, Spanish, and cowboy heritage. Stops on the way: • 🏡 Santa Fe Plaza & Canyon Preserve trail • 🛣️ Turquoise Trail scenic drive • 🚠 Sandia Peak Tramway (viewpoint)
9

Albuquerque

Day 9-10
⛰️ Day 9 – Albuquerque → Gallup (NM) Travel through lava fields and mesas as Route 66 cuts through New Mexico’s volcanic landscapes. Rustic diners and legendary motels line your way west. Stops on the way: • 🥞 66 Diner breakfast spot • 🌋 El Malpais Lava Falls Trail • 🏨 El Rancho Hotel (Gallup)
10

Gallup

Day 10-11
TStep back in time — literally — among ancient petrified trees and painted deserts. Finish the day with a classic Arizona sunset. Stops on the way: • 🌈 Painted Desert Rim Trail • 🏺 Petrified Forest National Park • 🎸 “Standin’ on the Corner” (Winslow)
11

Winslow

Day 11-12
Today’s route mixes science, scenery, and mountain vibes. From a giant meteor impact site to pine forests and Route 66 bars, Flagstaff has it all. Stops on the way: • ☄️ Meteor Crater Rim Trail • 🏞️ Walnut Canyon Island Trail • 🍻 Historic Downtown Flagstaff
12

Flagstaff

Day 12-13
One of the trip’s highlights — the world-famous Grand Canyon! Marvel at epic viewpoints before returning to the desert highway. Stops on the way: • 🏜️ Grand Canyon • 🚗 Seligman Historic Route 66 Town • 🛢️ Hackberry General Store
13

Kingman

Day 13-14
Say hello to wild burros, sand dunes, and vintage motels. The desert unfolds in surreal colors as you cross into California. Stops on the way: • 🐴 Oatman Ghost Town & Burros • 🏜️ Sitgreaves Pass Scenic View • 🏖️ Kelso Dunes (Mojave Preserve)
14

San Bernardino

Day 14-15
Your grand finale — the Pacific Ocean! Cruise through Los Angeles’ historic Route 66 neighborhoods and finish with your feet in the sand. Stops on the way: • 🌲 Angeles National Forest lookouts • 🌴 Beverly Hills sign & Boulevard drive • 🏁 Route 66 End Sign at Santa Monica Pier
15

Santa Monica

Day 15-16
Your Route 66 journey ends where dreams begin — Los Angeles! Spend the final day soaking up California vibes: palm-lined boulevards, movie history, and ocean breezes. Whether you’re relaxing at the beach or catching a flight home, it’s the perfect wrap-up to an unforgettable adventure. Stops on the way: • 🎥 Hollywood Sign viewpoint & Walk of Fame • 🌴 Venice Beach & Santa Monica shopping time • ✈️ LAX airport drop-off (if needed)
Trip Summary
Accommodation
Bed & Breakfast & Hotel
16 days trip
Chicago, Springfield & 13 more
Transportation
Car
What's excluded?
Flights to Chicago and from LA
Lunch & Dinner
Why JoinMyTrip?
Trusted platform used by 150K+ TripMates
Have A Question?
Live Chat with our experts 24x7
Unique Trips hosted by Experienced Travellers
Secure Payments to ensure your money is always safe