Route 66 stretches 2,400 miles from Chicago's Lake Shore Drive to Santa Monica Pier. This guide cuts through the myth to give you what you actually need: the best stops by state, realistic time estimates, where to sleep in historic motels, and the practical details that make the difference between a great trip and a stressful one.
The Route: Chicago to Santa Monica
Route 66 officially begins at the intersection of Michigan Avenue and Adams Street in Chicago, though most road trippers mark the true start at Lake Shore Drive, where a bronze shield marks the pavement. From there, the Mother Road runs southwest through eight states before ending at Santa Monica Pier, where the “End of the Trail” sign stands above the Pacific.
The historic alignment covers roughly 2,400 miles, but you won’t drive the same road from 1926 for the entire route. Decades of bypasses, realignments, and Interstate construction broke the old highway into segments. That’s part of the experience: hunting down surviving old alignments, sometimes narrowing to a cracked two-lane strip between ranch fences, while I-40 runs a quarter mile away carrying semis at 80 mph.
The eight states you’ll cross, in order:
- Illinois: 300 miles, from Chicago south to the Missouri border near St. Louis
- Missouri: 317 miles through the Ozarks to Joplin
- Kansas: Just 13 miles through Galena and Baxter Springs (easily skipped, but worth it)
- Oklahoma: 392 miles, the longest stretch of original alignment
- Texas: 178 miles through Amarillo and the Panhandle
- New Mexico: 487 miles from Tucumcari to Gallup
- Arizona: 401 miles including the best-preserved old alignment
- California: 315 miles from Needles across the Mojave to the Pacific
Best Time to Drive Route 66
The Route 66 driving season runs April through October, but the sweet spots are April–May and September–October, when temperatures are manageable across all eight states. Summer is peak season: expect crowds at major landmarks, higher motel rates, and brutal heat in the desert stretches of New Mexico, Arizona, and California (easily 110°F in the Mojave in July).
Winter is the wildcard. Mountain sections in New Mexico and Arizona can close with snow, and many smaller roadside attractions shut November through March. That said, winter offers empty roads, cheap rooms, and a melancholy quality to the old towns that’s hard to find in August.
- April–May: Wildflowers in the Southwest, mild temps everywhere, moderate crowds
- June–August: Peak season, with all attractions open, but desert heat is serious; start driving by 7 AM
- September–October: Best overall; crowds thin, temps drop, fall colors in the Ozarks
- November–March: Cheap and quiet, but plan for some closures and possible mountain road issues
How Long Does Route 66 Take?
Ten days is the absolute minimum if you’re driving without detours and skipping whole states. Two weeks gives you enough time to do it properly without rushing every morning. Three weeks lets you breathe: take the Petrified Forest side trip, spend two nights in Albuquerque, explore the Grand Canyon from Williams.
Most people regret going too fast. The towns that look like nothing on a map (Pontiac, Illinois; Miami, Oklahoma; Tucumcari, New Mexico) turn out to be the best part. Budget at most 300 miles of driving per day if you want to stop at anything.
Sample itinerary by day count:
- 10 days: Fast drive, highlights only (Cadillac Ranch, Petrified Forest, Santa Monica)
- 14 days: Comfortable pace, includes most major stops, some flexibility
- 21 days: Full experience with Grand Canyon detour, Santa Fe side trip, and time to wander
Illinois & Missouri: Starting Strong
Chicago’s starting point at Michigan and Adams is underwhelming: just a plaque on the sidewalk downtown. Get the photo, then head south through the city’s South Side neighborhoods before breaking into the flatlands of central Illinois. The drive through here is honest about what Route 66 is: a state road through small American towns, not a scenic highway through dramatic landscape.
The stops that matter in Illinois: the Gemini Giant in Wilmington (a fiberglass muffler man holding a rocket, one of the classic roadside giants), the Route 66 Hall of Fame in Pontiac (with a well-curated collection of road artifacts), and in Springfield, Cozy Dog Drive In, which has claimed to have invented the corn dog since 1946.
Missouri’s Route 66 runs through the Ozark Plateau, and the stretch through the hills between St. Louis and Springfield is genuinely beautiful, winding two-lane through forested ridges, old bridges, and river valleys. Don’t skip Meramec Caverns near Stanton (Jesse James supposedly hid here; the barn advertising still covers every fence post for miles). In the Ozarks, Carthage and Joplin have good stretches of original alignment through downtowns that look largely unchanged from the 1950s.
Oklahoma & Texas Panhandle: Neon and Open Sky
Oklahoma has the longest surviving section of original Route 66 alignment, and it shows. This state takes the highway seriously. Tulsa has genuine art deco architecture downtown, and the Cyrus Avery Centennial Plaza near the old 11th Street Bridge is one of the best photo spots on the entire route. The Blue Whale of Catoosa, a massive smiling whale sculpture in a pond, is genuinely delightful and worth the five-minute detour.
Oklahoma’s small towns have neon signs, working diners, and almost no tourists. Clanton’s Café in Vinita has been open since 1927. Ed Galloway’s Totem Pole Park in Foyil is eccentric and wonderful. This is Route 66 without the Instagram crowd.
Texas gives you 178 miles through the flat Panhandle, not particularly scenic, but home to one of the route’s most photographed stops. Cadillac Ranch outside Amarillo is ten half-buried Cadillacs nose-first in a wheat field, spray-painted by visitors continuously since 1974. Bring a can of spray paint. Amarillo’s walkable downtown strip along historic 6th Street has antiques, vintage shops, and good food, far better than the tourist corridor suggests.
New Mexico & Arizona: The Soul of Route 66
Tucumcari, New Mexico is where Route 66’s neon era is most intact. More than two dozen original motel and restaurant neon signs still light up the main drag at night, many restored, some original. Arrive close to dusk to see them properly. The Blue Swallow Motel is the most photographed, but the Palomino and Safari Motel signs are equally vivid. Plan to spend a night here.
Albuquerque’s Central Avenue follows the original Route 66 alignment through the city, past the Nob Hill neighborhood’s 1940s commercial strip. The Kimo Theatre (1927, Pueblo Deco style) is stunning. If you have time, the side trip to Santa Fe (58 miles north on I-25) adds a day but is worth it for the Plaza and Museum of International Folk Art.
Arizona has the best-preserved driving on the entire route. The Petrified Forest National Park and adjacent Painted Desert should not be skipped; allow half a day minimum. The stretch from Seligman to Kingman is the most iconic surviving piece of old Route 66: 90-plus miles of two-lane through scrubland and cattle country, virtually traffic-free, almost identical to 1955. Stop in Seligman at Delgadillo’s Snow Cap Drive-In; Angel Delgadillo is the man most responsible for saving Route 66 in Arizona. The Hackberry General Store, about 30 miles east of Kingman, is a perfectly preserved roadside relic.
California: Desert to the Pacific
After Arizona, the route drops into Kingman and then crosses into California at Needles, where the Mojave Desert takes over. This stretch from Needles to Barstow (about 150 miles) is one of the most desolate sections of the drive. Fill your tank in Needles. Summer temperatures regularly exceed 115°F, and services are sparse. Amboy is a near-ghost town with a restored Roy’s Motel & Café sign, one of the great neon photo stops on the western end.
From Barstow, the route climbs through the Cajon Pass into the Los Angeles Basin. San Bernardino has a Route 66 Museum worth an hour. The Wigwam Motel in Rialto (seven teepee-shaped concrete rooms built in 1949, individually landmarked, still operating) is one of the iconic sleeps on the western end.
The finish at Santa Monica Pier is earned. The “End of the Trail” sign is at the pier’s entrance, and the Pacific Ocean is right there. The drive from Chicago to this point, if you’ve done it properly, takes two to three weeks. You’ll have driven through eight states, eaten at diners open since 1927, slept in teepees and neon motels, and crossed three time zones.
Classic Motels Worth Booking Early
The best overnight experiences on Route 66 are the surviving historic motels. Book them well in advance during peak season, as many have only 10–20 rooms and fill months ahead:
- Blue Swallow Motel, Tucumcari NM: The most iconic surviving Route 66 motel, individually landmarked, restored neon. Book 2+ months ahead in summer.
- Wigwam Motel, Rialto CA: Teepee-shaped concrete rooms from 1949. Also has a sister property in Holbrook, AZ.
- El Rancho Hotel, Gallup NM: Full-service hotel where film stars stayed during 1940s–50s Westerns. Named rooms (John Wayne Suite, etc.). Still excellent.
- La Posada Hotel, Winslow AZ: Restored Fred Harvey hotel from 1929, designed by Mary Colter. The most elegant place to sleep on the entire route.
- Munger Moss Motel, Lebanon MO: A Route 66 institution in the Ozarks, owned by the same family since 1971, neon sign beautifully maintained.
- Wagon Wheel Motel, Cuba MO: Simple, clean, charming, and one of the most original-condition motels on the route.
Food, Gas, and Getting There
Navigation is the trickiest part for first-timers. Route 66 doesn’t run continuously; you’ll frequently jump on I-40 to bypass sections where the old road no longer exists. The EZ66 Guide book (a turn-by-turn strip guide, the standard reference for decades) and the Route 66 Road Ahead app (GPS-based historic alignment tracking) make this manageable. Bring both.
Gas is the practical concern most people underestimate. In the Texas Panhandle, New Mexico, and especially the California desert, stations can be 50–80 miles apart on the historic alignment. Keep the tank above half in these stretches.
Standout meals along the way:
- Lou Mitchell’s, Chicago IL: Traditional first breakfast before departure, open since 1923
- Rock Café, Stroud OK: Featured in the Pixar film Cars, rebuilt after a 2008 fire, genuinely good food
- Midpoint Café, Adrian TX: Exactly halfway between Chicago and Los Angeles (1,139 miles each way); serves “ugly crust” pie
- 66 Diner, Albuquerque NM: Classic diner in a 1940s Whiting Brothers gas station building
- Delgadillo’s Snow Cap, Seligman AZ: Eccentric roadside institution, go for the experience as much as the food
- Oatman Hotel, Oatman AZ: Wild burros wander the street outside; the chili is good
One decision every Route 66 driver faces: east to west or west to east? Driving west (Chicago to Santa Monica) is the traditional direction and has the psychological advantage of moving toward the ocean. The afternoon sun will be in your eyes in the desert, so bring polarized sunglasses. If you’re flying in and out, both Chicago O’Hare and LAX are major hubs with comparable fares.
Frequently Asked Questions About Historic Route 66: The Complete Road Trip Guide from Chicago to Santa Monica
How long does it take to drive Route 66?
Driving Route 66 from Chicago to Santa Monica takes a minimum of 10 days if you push hard and skip some states. Most travelers need 14 days to hit the major stops comfortably. Three weeks is ideal if you want side trips like the Grand Canyon from Williams, Arizona. Budget no more than 300 miles of driving per day if you plan to stop at any attractions.
Is Route 66 still drivable today?
Yes, the vast majority of Route 66 is still drivable, though not as a continuous highway. The old alignment exists in segments - some beautifully preserved, others interrupted by Interstate 40. Navigation apps like Route 66 Road Ahead and guidebooks like the EZ66 Guide help you stay on historic alignment when it exists and use I-40 when gaps appear. About 85% of the original alignment is accessible by car.
What is the best starting point for Route 66?
The traditional and most popular direction is west, from Chicago to Santa Monica. The official start is Michigan Avenue and Adams Street in Chicago, Illinois. Some travelers drive east to west for the psychological reward of reaching the Pacific Ocean at the end. Both directions work; driving west means the afternoon sun is in your eyes in the desert - polarized sunglasses help significantly.
Which states have the best Route 66 scenery?
Arizona and New Mexico offer the most dramatic scenery: the Painted Desert, Petrified Forest, red rock mesas, and pinyon-juniper hills. The Seligman-to-Kingman stretch in Arizona is the most scenic and best-preserved driving segment on the entire route. Missouri's Ozark hills offer beautiful river valley scenery. Illinois and Texas are largely flat, but Illinois has excellent roadside culture and Texas has Cadillac Ranch.
What are the must-see stops on Route 66?
The stops most drivers consider essential: Cadillac Ranch (Amarillo, TX), Blue Whale of Catoosa (OK), Blue Swallow Motel neon district (Tucumcari, NM), Petrified Forest National Park (AZ), the Seligman-to-Kingman old alignment (AZ), Hackberry General Store (AZ), Wigwam Motel (Rialto, CA or Holbrook, AZ), Roy's Motel and Cafe (Amboy, CA), and the Santa Monica Pier end sign. Add Gemini Giant (Wilmington, IL) and Meramec Caverns (MO) in the east.
How much does a Route 66 road trip cost?
For two people driving 14 days, expect roughly $350-500 for gas, $800-1,400 for accommodation ($55-100 per night at historic motels), $600-1,000 for food, and $200-400 for attraction entry fees including Petrified Forest National Park. Total budget runs $2,000-3,300 for two people, or $1,000-1,700 per person. Book historic motels well in advance for summer travel - many sell out months ahead.
