East to West or West to East? The Route 66 Direction Decision, Settled

It is the second question every Route 66 planner asks, right after “how long does it take?”: which direction should I drive it? The traditional answer — east to west, Chicago to Santa Monica, following the Okies and the Dust Bowl migrants and a generation of postwar Americans heading toward California — carries the weight of history. The contrarian answer — west to east, starting at the End of the Trail on the Santa Monica Pier and driving toward Chicago — has its own logic, its own advocates, and its own genuine pleasures. Both directions cover the same 2,448 miles of American road. Both pass the same landmarks, the same neon signs, the same two-lane curves through the Ozarks and the desert. But they are meaningfully different experiences, and the direction you choose shapes the story you tell when you get home.

The short answer: east to west is better for most drivers, especially first-timers. The longer answer — which is the one worth reading before you book your flights — is that the right direction depends on where you live, what you’re trying to photograph, how you want to feel at the end, and whether the logistics of a one-way road trip across the country work in your favor. This guide covers every factor, honestly, so you can make the choice that fits your trip.

East to West vs. West to East: Head-to-Head Comparison

Every major factor in the direction decision, compared side by side. The Edge column indicates which direction has the advantage — or whether the factor is a genuine tie.

Factor	East → West  (Chicago to Santa Monica)	West → East  (Santa Monica to Chicago)	Edge
Classic direction	✔ The traditional, historically correct direction — how the Okies traveled, how the guidebooks read	Reverse of the traditional narrative; you build toward Chicago rather than the sea	E→W
Iconic finish	✔ Santa Monica Pier — the End of the Trail sign, the Pacific Ocean, a payoff that earns its emotion	Chicago’s Begin sign — thrilling as a start, anticlimactic as a finish for many	E→W
Iconic start	Chicago Begin sign — strong, urban energy to launch the trip	✔ Santa Monica Pier — beginning at the End of the Trail is a genuinely moving and photogenic launch	Tie
Photography light (morning)	✔ Morning sun behind you for most westbound driving — front-lit landscapes across the Great Plains and desert	Morning sun in your eyes heading east; landscapes often backlit in AM hours	E→W
Photography light (golden hour)	Sunsets over the desert and mountains — spectacular	✔ Sunrises over the desert and mountains heading east — equally spectacular and less photographed	Tie
Logistics (flights)	Fly into Chicago O’Hare or Midway; fly home from LAX or Burbank	✔ Fly into LAX, fly home from Chicago — for West Coast residents, this eliminates the cross-country positioning flight	Depends
Narrative arc	✔ Builds from Midwest urban (Chicago) through small towns to desert to the Pacific — matches the American westward mythology Route 66 embodies	Begins at the sea and moves toward the interior — a different story, but the arc feels less resolved to most drivers	E→W
Desert heat strategy	You arrive in the Arizona/California desert late in the trip — plan season carefully	✔ You hit the desert first — useful if traveling in shoulder season and want to clear Arizona before summer heat peaks	W→E
Crowd experience	Same crowd levels either direction — no meaningful difference	Same crowd levels either direction — no meaningful difference	Tie
Guidebook / GPS support	✔ Virtually all Route 66 guidebooks, apps, and mile marker systems run west — designed for E→W travel	Requires reversing all guidebook mileages and directions; some apps support it, most do not natively	E→W
Wind (Great Plains)	Prevailing westerly winds are often a headwind through Kansas, Oklahoma, and Texas	✔ Prevailing westerly winds often become a tailwind through the Great Plains states heading east	W→E
The emotional experience	✔ The majority of travelers report E→W as the more emotionally satisfying direction — the Pacific as a destination carries weight that Chicago as a destination, while wonderful, does not quite match	A genuinely different and valid experience — but the surveys, the forums, and the veterans consistently favor E→W for first-timers	E→W

The Case for East to West: Chicago to Santa Monica

The argument for driving east to west is essentially the argument for Route 66 itself. The highway was built to carry people westward — from the Midwest toward California, toward opportunity, toward the Pacific. John Steinbeck’s “The Grapes of Wrath” travels west. The Dust Bowl migrants traveled west. The postwar Americans who drove it for vacation traveled west. The mythology of Route 66 is a westward mythology, and driving east to west means you are traveling inside that story rather than against it.

The Chicago Beginning

Starting at the Begin Historic Route 66 sign at the intersection of Adams Street and Michigan Avenue in downtown Chicago is a genuinely thrilling way to launch a road trip. The city energy — the architecture, the lake, the noise and scale of one of America’s great urban centers — contrasts dramatically with the small-town Illinois corridor that begins almost immediately as you head southwest toward Joliet, Dwight, and Pontiac. That contrast — urban start, rural middle, desert finish, ocean end — is the Route 66 experience in miniature, and it unfolds naturally when you travel east to west.

The Santa Monica Finish

The emotional argument for east to west comes down to a single moment: standing at the End of the Trail sign on the Santa Monica Pier, with the Pacific Ocean behind you and 2,448 miles of American road in the rearview mirror. It is one of the most satisfying finish lines in road tripping — not because it is easy to reach, but because the accumulated weight of the journey makes it feel earned. The pier, the ocean, the carousel, the sunset: they are the payoff that the entire route builds toward, and most experienced Route 66 travelers agree that arriving at Santa Monica going west is more emotionally resonant than departing from it going east.

Photography: Front-Lit Landscapes

For photographers, east to west has a practical advantage that is easy to underestimate until you’re standing in it: the morning sun is generally behind you as you drive west. This means the landscapes in front of you — the Oklahoma plains, the Texas Panhandle, the New Mexico desert, the Arizona canyon country — are front-lit in the morning hours, which is when the best travel photography happens. Driving east to west, you spend your mornings watching the sun illuminate the road ahead. Driving west to east, you spend those same mornings driving into the sun with landscapes in silhouette.

The exception is sunsets: driving west, you end each day chasing the sun, which means your evening stops are often backlit. Driving east, you get the sunrise illuminating the landscapes behind you — which is its own beauty. But the morning front-light advantage of east to west is the more valuable photographic asset for most of the route’s great landscape sections.

Guidebooks and Navigation

Every major Route 66 guidebook is organized east to west. The EZ66 Guide by Jerry McClanahan — the definitive turn-by-turn navigation guide — runs Chicago to Santa Monica. The Route 66 Adventure Handbook runs east to west. Mile markers, exit references, and landmark descriptions in virtually every planning resource assume westbound travel. Driving east to west means all of your planning materials work with you rather than requiring constant mental reversal of directions and distances.

The Narrative Arc

Route 66 has a narrative structure. It begins in the urban Midwest, passes through the agricultural heartland, crosses the high plains, enters the desert, climbs and descends the mountains, and ends at the Pacific Ocean. That sequence — interior to coast, familiar to alien, landlocked to oceanic — is a story with a beginning, a middle, and an end. Driving east to west, you experience it in the order it was meant to be experienced. Driving west to east, you experience it backwards — which is interesting but is a different story, one that ends in Chicago rather than at the sea.

The Case for West to East: Santa Monica to Chicago

The case for driving west to east is real and deserves to be stated fairly. For specific travelers in specific circumstances, it is genuinely the better choice — not just an acceptable alternative but the superior approach. Here is the honest argument for it.

West Coast Residents: The Logistics Win

If you live in California, Oregon, or Washington, the logistics of east-to-west travel require a cross-country positioning flight to Chicago before the trip even begins. That flight costs money and time, and it means arriving at the start of a 2,448-mile drive already fatigued from air travel. Driving west to east solves this: you start at the Santa Monica Pier — which may be a short drive from your home — and drive to Chicago, where you can easily fly home from O’Hare or Midway. For West Coast residents, the logistics of west-to-east travel are simply more efficient, and the efficiency matters over a trip of two weeks or longer.

The Santa Monica Launch

Starting at the End of the Trail sign on the Santa Monica Pier is a genuinely moving experience in either direction. As a launch point, the pier has real power: the scale of the Pacific Ocean behind you, the knowledge that the road ahead runs 2,448 miles to Chicago, and the symbolism of beginning where so many journeys ended gives the west-to-east start its own emotional weight. Several devoted Route 66 travelers describe the west-to-east launch as more dramatic as a start than the Chicago Begin sign — the pier is a more visually spectacular location than a downtown Chicago street corner, even a storied one.

The Desert First: A Weather Strategy

Driving west to east means you reach the Arizona and California desert sections first — within the first two to three days of your trip. For travelers driving in spring or early summer, this can be a deliberate weather strategy: you clear the desert (the most heat-dangerous section of Route 66) early in the trip, before the worst of the summer heat arrives, and arrive in the cooler and more forgiving Midwest states later in the journey. This strategy works particularly well for April and May departures, when the Arizona desert is warm but manageable in the first week and the Oklahoma and Illinois corridor may still be in comfortable spring temperatures by the time you arrive.

The Prevailing Wind Advantage

The Great Plains states of Kansas, Oklahoma, and Texas are dominated by prevailing westerly winds — winds that blow from west to east. Driving east to west through these states means driving into the prevailing wind for hundreds of miles, which increases fuel consumption and can be genuinely tiring on the flat, exposed Panhandle and Oklahoma sections. Driving west to east means the prevailing wind is behind you through these states — a tailwind that improves fuel efficiency slightly and makes the driving feel less effortful. The difference is modest and weather-dependent, but over hundreds of miles of exposed Great Plains driving, it is a real factor.

Seeing the Route Differently

Every experienced Route 66 driver who has traveled the route in both directions reports the same thing: it feels like a different road going the other way. The specific details you notice — the angle of light on a building facade, the view of an approaching landmark, the sequence of towns in a corridor — change completely when you reverse direction. Drivers who have traveled east to west multiple times consistently describe their first west-to-east trip as a genuine revelation: familiar landmarks that become new, sections that seemed uninteresting in one direction that reveal depth in the other. If you have already driven Route 66 east to west, driving it west to east is the right choice for your next trip

Which Direction Is Right for You? A Traveler Profile Guide

Use this table to match your specific situation to the direction that fits best. The recommendations are based on the full range of factors — logistics, photography, weather strategy, emotional experience, and practical planning resources.

Your Profile	Recommended Direction	Reason
First-time Route 66 traveler	East → West	The traditional direction, guidebooks written for it, and the Santa Monica payoff is the right way to experience the route the first time.
West Coast resident (CA, OR, WA)	Either works	Starting in Santa Monica eliminates a positioning flight to Chicago. Many West Coast regulars drive W→E specifically to arrive in Chicago for a city stay.
Midwest resident (IL, MO, OK)	East → West	You’re already at the start. Drive to the Pacific and fly home — no deadhead travel.
Passionate photographer	East → West	Front-lit landscapes across the Great Plains and desert for most of the drive. Morning light is behind you; desert and mountain sunsets in front.
Repeat Route 66 driver	West → East	Experiencing the route in reverse is genuinely revelatory — you see different things, notice different details, and it feels like a new road.
Driving in summer heat	East → West	You can time your desert crossing (AZ/CA) for the tail end of your trip in late fall, or plan to be in the desert early in the morning before heat peaks.
Driving in spring or fall	Either — lean E→W	Season matters more than direction in shoulder seasons. E→W for first-timers; W→E for those who want to finish in Chicago during peak fall foliage season.
Using Route 66 guidebooks	East → West	Every major guidebook — EZ66, Route 66 Adventure Handbook, Along the Mother Road — is organized west. Reversing mileages adds friction.
Budget traveler (fuel cost focus)	West → East	Prevailing westerly winds can provide a minor tailwind advantage across the Great Plains states, though the difference is modest.
Centennial 2026 travelers	East → West	Most Centennial events will run east to west following the traditional direction. Guidebooks, group tours, and organized Centennial rides default to E→W.

Practical Logistics: Planning a One-Way Route 66 Trip

Driving Route 66 end-to-end in one direction requires solving the one-way vehicle logistics problem: you start in one city and finish in another, roughly 2,100 air miles apart. There are four approaches, each with trade-offs.

Option 1: Fly One Way, Drive One Way (Most Popular)

The most common approach for full-route travelers: fly to your starting city, drive the full route, fly home from the finishing city. For east-to-west drivers, this means flying into Chicago (O’Hare or Midway) and flying home from Los Angeles (LAX, Burbank, Long Beach, or Ontario). For west-to-east drivers, it means flying into Los Angeles and flying home from Chicago. Both routes have abundant, competitively priced flights.

Key considerations for this approach:

• One-way car rental: Major national rental companies (Enterprise, Hertz, Avis, Budget) offer one-way rentals between Chicago and Los Angeles. Expect a one-way drop fee that can range from $100 to $400+ depending on the company, the vehicle, and the rental period. Book early and compare prices across companies.
• Your own vehicle: If you prefer to drive your own vehicle, you will need to return to your starting city after the trip — either by flying back to pick up the car (if you drove from your home city) or by arranging a return positioning trip.
• Shipping your vehicle: For travelers using their own vehicle who do not want to drive back, auto transport companies can ship your car from your ending city back to your home. This adds cost but eliminates the return trip.

Option 2: Round Trip — Drive Both Directions

Some Route 66 veterans drive the route in both directions as a single trip — east to west, turn around, and drive west to east home. This approach doubles the mileage and the time required but eliminates all one-way logistics. It also delivers the experience of seeing every section of Route 66 in both directions, which, as noted above, feels like two different roads. This approach is most common among retirees and full-time RVers who have the time and the motivation.

Option 3: Partial Route — Start and End in the Same Region

For travelers who do not want to manage cross-country one-way logistics, a partial route that begins and ends within the same city or region is a practical solution. Examples: drive Chicago to Oklahoma City and fly home from OKC; drive Los Angeles to Albuquerque and fly home from ABQ; drive Albuquerque to Chicago and fly home from ORD. These partial routes avoid the full cross-country one-way logistics while still delivering genuine Route 66 experiences. See the article on How Long Does It Take to Drive Route 66 for detailed partial-route itinerary options.

Option 4: The Driveaway / Relocation Vehicle

A lesser-known option for budget travelers: driveaway services connect people who need to relocate a vehicle from one city to another with drivers who need a free or low-cost vehicle for a long trip. Services like Auto Driveaway have historically offered vehicles that need to be moved from Chicago to Los Angeles or vice versa. The driver gets a free vehicle to use for the trip; the vehicle owner gets their car relocated without paying for transport. The trade-off is schedule inflexibility — you drive the route on the owner’s timeline, not your own — but for budget travelers, it is worth investigating.

Direction and the Route 66 Centennial (2026)

The Route 66 Centennial — the 100th anniversary of the highway’s commissioning on November 11, 2026 — will generate organized tours, events, and group drives across all eight states throughout the year. The overwhelming majority of organized Centennial events will follow the traditional east-to-west direction, mirroring the historic travel pattern. Group tours departing from Chicago and arriving in Santa Monica will dominate the Centennial calendar. If you are planning to participate in organized Centennial events or drive alongside other Route 66 travelers during the anniversary year, east to west is the direction to travel

For solo Centennial travelers who want to experience the anniversary without the crowds of organized group tours, west to east in October or November 2026 offers an interesting counter-programming option: you will encounter the organized Centennial convoys head-on (literally) rather than following in their wake, and you will arrive in Chicago precisely as the anniversary date approaches — a genuinely memorable finish to a Centennial road trip. Check the Route 66 Centennial 2026 page for the full event calendar as it develops.

Direction Notes: How Each State Feels Going Each Way

Beyond the broad arguments, each state has specific characteristics that make it meaningfully different depending on which direction you’re traveling.

Illinois — Better Eastbound as a Finish

Driving east to west through Illinois means the excitement of leaving Chicago anchors the start of your trip — exactly right. Driving west to east means arriving in Chicago at the end of 2,448 miles, which many travelers find anticlimactic compared to arriving at the Santa Monica Pier. The exception: travelers who love Chicago and want to end with several days in the city find west-to-east deeply satisfying as a finish.

Missouri — Better Westbound (Ozarks at Full Speed)

The Missouri Ozark two-lane alignments are equally spectacular in either direction — but driving them westbound, early in the trip, means you are still fresh, still stopping frequently, still exploring every side road. By the time most eastbound travelers reach Missouri late in a west-to-east trip, fatigue can lead to more interstate miles and fewer historic alignment miles through the hills.

Oklahoma — Equally Good in Both Directions

Oklahoma has more original Route 66 alignment than any other state, and its character — the small towns, the two-lane curves, the Route 66 commercial heritage — is equally rewarding in either direction. The specific sequence of stops changes (you approach the Blue Whale from a different direction, the National Route 66 Museum comes earlier or later), but Oklahoma is genuinely direction-neutral in its rewards.

Texas — Better Westbound (Cadillac Ranch Approach)

Driving east to west through the Texas Panhandle means approaching Cadillac Ranch from the east — the correct side for morning photography, with the sun behind you and the ten Caddies lit from the front. Driving west to east means approaching from the west, with morning light often directly in your face as you shoot toward the sunrise. For photographers, Texas is better westbound.

New Mexico — Better Westbound (Tucumcari Arrival at Dusk)

One of the iconic Route 66 experiences is arriving in Tucumcari, New Mexico after dark, with the surviving neon signs — the Blue Swallow Motel, the Pow Wow Inn, the Tepee Curios — blazing against the high desert night. Driving east to west, you approach Tucumcari from the east in the late afternoon or evening, which is precisely the right timing for neon. Driving west to east, you leave Tucumcari heading east — usually in the morning — and miss the neon hour entirely. New Mexico is better westbound.

Arizona — Equally Good, but Oatman is Better Westbound

Arizona is spectacular in either direction — the Painted Desert, Petrified Forest National Park, and the Flagstaff-to-Seligman corridor are equally rewarding going either way. The specific argument for westbound Arizona is the descent from Sitgreaves Pass into Oatman: driving west, you descend into Oatman from the high desert — a dramatic, winding mountain road that culminates in the Wild West character of the old gold-mining town. Driving east, you climb out of Oatman, which is the less cinematic direction of travel on this particular section.

California — Better Westbound (The Pacific Payoff)

The California section — from Needles through the Mojave, the Inland Empire, Pasadena, and the Los Angeles basin to Santa Monica — is the section that most clearly favors westbound travel. Arriving at the Santa Monica Pier from the east, with the Pacific Ocean suddenly appearing at the end of the road after 2,400 miles of landlocked American landscape, is one of the great road trip moments in the country. That moment is only available to east-to-west travelers. Arriving at Santa Monica going east and immediately turning inland toward Los Angeles is a fine experience — but it is not the same thing.

More Route 66 Trip Planning Resources

Route 66 — Complete Travel Guide — The full overview of all 2,448 miles: history, alignments, and state-by-state planning.

How Long Does It Take to Drive Route 66? — Realistic drive times for the full route and every partial-route option, with daily mileage guidance and state-by-state breakdowns.

Best Time of Year to Drive Route 66 — Season-by-season weather, crowd levels, and budget guide — because timing often matters more than direction.

Route 66 in Illinois — The first state eastbound: Chicago’s Begin sign, the Gemini Giant, Springfield, and the southern Illinois farmland corridor.

Route 66 in Missouri — The Chain of Rocks Bridge, Meramec Caverns, and the Ozark two-lane alignments.

Route 66 in Kansas — Just 13 miles, but the Rainbow Bridge and Galena are essential stops in either direction.

Route 66 in Oklahoma — More original Route 66 mileage than any other state. Direction-neutral in its rewards.

Route 66 in Texas — Cadillac Ranch, the midpoint at Adrian, and the Panhandle sky.

Route 66 in New Mexico — Tucumcari neon, Santa Rosa, Albuquerque’s Central Avenue, and Gallup.

Route 66 in Arizona — The Painted Desert, Petrified Forest, Flagstaff, Seligman, and the Oatman mountain descent.

Route 66 in California — Needles through the Mojave, the Inland Empire, and the End of the Trail at the Santa Monica Pier.

Route 66 Centennial 2026 — The 100th anniversary of Route 66 is November 11, 2026. Events, organized tours, and Centennial planning resources.

Route 66 State Associations — The eight state associations for local event calendars, membership, and preservation updates.