Route 66 Travel Itinerary

Updated September 2026 · Vacation Checklists

A full Route 66 travel itinerary runs about 2,448 miles from Chicago to Santa Monica through eight states, and two weeks is the length that works. Ten days is doable but rushed, and three weeks lets you take the detours. Drive it east to west, budget roughly 175 to 200 miles a day, and accept from the start that the road is no longer one continuous highway.

Get your gear sorted first with our free packing list generator, then use the day-by-day plan below to shape the drive.

Updated September 2026. Route 66 businesses are mostly small and independent, and hours, seasonal closures, and even entire stops change from year to year. Check current hours before you build a day around any single place, and check state DOT sites for road conditions in winter.

A note on numbers. No dollar figures on this page. Fuel, motel rates and one-way rental drop fees move by state, by season and by the week you book, and an amount printed here would be wrong for most readers. What you get instead is the mileage, the night count, the shape of the budget, and which lines you actually control.

The Basics Before You Plan Anything

It is not one road anymore. Route 66 was decommissioned as a US highway in 1985. What exists today is a patchwork of state-signed Historic Route 66 alignments, county roads, business loops, frontage roads, and a few stretches that are simply gone under the interstates that replaced them: I-55, I-44, I-40, I-15, and I-10.

That has one practical consequence: your phone's default navigation will not follow it. Ask a mapping app for Chicago to Santa Monica and it will put you on interstates and save you two days you did not want to save. You need a Route 66 specific guide or app that gives turn-by-turn directions for the old alignments. The long-running EZ66 Guide is the one most drivers carry, and there are several dedicated apps.

Drive east to west. Chicago to Santa Monica. The sun is behind you in the morning, the classic narrative runs that direction, and the finish at the Santa Monica Pier is a real ending. West to east works fine logistically, but you finish in a Chicago parking garage.

Eight states, wildly uneven. The mileage split matters for planning.

Kansas gets 13 miles, and they are excellent 13 miles. Oklahoma has the most drivable original pavement of any state. Arizona has the longest uninterrupted surviving stretch, roughly 160 miles from Seligman to Topock.

How to Build Your Route 66 Travel Itinerary

Work in this order, and the plan builds itself.

1. Pick your total days first. Everything else is downstream of this. Ten days means you skip detours. Fourteen is the comfortable version. Twenty-one lets you add the Grand Canyon, Santa Fe, and slow mornings.
2. Divide the 2,448 miles by your driving days, not your total days. You want at least two days with almost no driving. On a 14-day trip that leaves 12 driving days, or about 200 miles per day. That sounds easy until you remember the old alignments run at 45 mph with stops every 20 minutes.
3. Fix the ends. Book your first night in Chicago and your last night near Santa Monica. Those two are the hardest and most expensive.
4. Fix three or four anchor nights. Tulsa, Amarillo, Tucumcari, Flagstaff. These are the towns with real lodging options and they space the trip well.
5. Leave the rest loose. Small-town motels rarely sell out outside peak weekends, and the freedom to stop when a place looks good is most of the point.
6. Plan the one-way car problem. A one-way rental from Chicago to Los Angeles carries a drop fee that can be substantial, so price it early. Flying into Chicago and out of LAX is normal for this trip.

The 14-Day Route 66 Itinerary

This is the version most people should drive. Mileage is approximate and reflects the historic alignments, not the interstate shortcuts.

Total driving: roughly 2,345 miles across 14 days, which is an average under 170 miles a day. That is deliberate. The mistake first-timers make is planning 300-mile days and then arriving everywhere after the good places have closed.

State by State: What Actually Earns the Stop

Illinois. The most polished stretch, with the best signage and a genuine museum culture. Start at the Begin Route 66 sign at Adams Street and Michigan Avenue in Chicago. Lou Mitchell's has been feeding drivers breakfast since long before the road was decommissioned. Pontiac's Route 66 Hall of Fame and Museum is worth an hour. Funks Grove sells maple sirup, spelled that way on purpose. Springfield gives you the Cozy Dog Drive In, where the corn dog on a stick has its origin story.

Missouri. Where the road was born, in the sense that the Springfield, Missouri chamber sent the telegram that settled the number 66. The Chain of Rocks Bridge crosses the Mississippi with a 22-degree bend in the middle, and it is now pedestrian and bicycle only, which makes it a walk rather than a drive. Meramec Caverns is the classic barn-advertised tourist cave. Carthage packs three good stops into one town: the 66 Drive-In, the Boots Court Motel, and Red Oak II.

Kansas. Thirteen miles and worth every one. Galena's Cars on the Route sits in an old Kan-O-Tex station with the tow truck that inspired a certain animated character. Riverton has a 1923 Marsh Arch bridge, one of the last of its kind on the route. You can drive the whole state in 20 minutes or spend a very pleasant three hours.

Oklahoma. The most original pavement of any state, including brick and concrete sections you can still drive. The Blue Whale of Catoosa is the most photographed roadside attraction on the route. Tulsa treats Route 66 as civic identity, with restored neon along 11th Street. Arcadia gives you the 1898 Round Barn and POPS with its wall of several hundred soda flavors.

Texas. Short and dense. The U-Drop Inn in Shamrock is an art deco Conoco station restored to full glory. Amarillo has Cadillac Ranch, where you bring a can of spray paint and add a layer to ten half-buried cars. Adrian marks the geographic midpoint: 1,139 miles to Chicago, 1,139 miles to Los Angeles, with a cafe built around that fact.

New Mexico. The neon state. Tucumcari's main drag at dusk is the single best neon experience on the route, and the Blue Swallow Motel is the one people book a year out. There is a genuine routing choice here: the pre-1937 alignment loops north through Santa Fe, adding roughly 100 miles and a day, while the post-1937 alignment runs straight from Santa Rosa to Albuquerque. Both are historically correct. Take the Santa Fe loop if you have the day.

Arizona. The most dramatic scenery. Petrified Forest National Park is the only national park that Route 66 ran directly through, and there is a rusted 1932 Studebaker marking the old roadbed. Holbrook's Wigwam Motel lets you sleep in a concrete tepee. Winslow has the corner. Seligman is the town that started the Historic Route 66 preservation movement, and the 160 miles west from there to Topock is the longest continuous original stretch left. Oatman has wild burros that will absolutely stick their heads in your car window, reached over the tight switchbacks of Sitgreaves Pass.

California. The Mojave crossing is the most demanding driving of the trip and the emptiest. Amboy's Roy's Motel and Cafe sits alone with its enormous sign. Then Barstow, the climb through Cajon Pass, San Bernardino, and a long urban run through the Los Angeles basin to the End of the Trail sign on Santa Monica Pier.

Our how to plan a road trip guide covers the general planning math, and the road trip packing list covers what lives in the front seat versus the trunk.

Best Time to Drive Route 66

Spring and fall are the answer for most people. If you drive in summer, do the Mojave and Arizona legs in the early morning and treat afternoon heat as a real hazard rather than a discomfort.

Worked Example: Budgeting a 14-Day Drive for Two

Five lines, in the order they matter. Work out the quantities here, then price them yourself the week you book.

Fuel. 2,345 miles driven on the historic alignments, plus roughly 200 miles of detours, backtracking, and town driving. Call it 2,550 miles. At 28 miles per gallon that is about 91 gallons, and a large SUV at 18 mpg turns the same drive into about 142 gallons. Fuel is the one line you can calculate to the gallon before you leave, so do that first, then multiply by whatever the pump is asking. Expect the pump to be kindest in Oklahoma and Texas and least kind in California, and budget the final leg high on purpose.

Lodging. 13 nights, and this is the line you actually control. Vintage motels along the route are consistently cheaper than the chains out by the interstate exits, and city nights in Chicago, St. Louis, and Santa Monica cost multiples of a small-town motel. Plan roughly ten route nights and three city nights, and book the three city nights early, because those are the ones that move most with demand.

Food. Diner breakfasts and lunches are the cheap part of this trip and one of the better parts of it. Two people eating diner food twice a day and a sit-down dinner most evenings will spend less per day than they would at home in a large city, and considerably less than a resort vacation. Pack a cooler and the number drops again.

Attractions. Most Route 66 stops are free, or charge a nominal admission collected in a coffee can by the door. The exceptions are the museums, the caverns, and the national park entries, and they are worth planning for as a group. If you will hit three or more federal sites, an annual America the Beautiful pass usually pays for itself on this route.

One-way rental. If you are not driving your own car, a two-week one-way rental with the drop fee is almost always the largest single line on the trip, larger than fuel and sometimes larger than lodging. Price it before you commit to the trip shape. A round trip from a single city can occasionally come in cheaper even after you add the extra flight, and that comparison is worth twenty minutes of your time.

Where it lands. Lodging and the one-way rental are the two lines that decide whether this is an inexpensive trip or an expensive one. Fuel and food barely move by comparison, and attractions are close to a rounding error. Attack the rental drop fee and the city nights, and the rest takes care of itself.

The Practical Stuff Nobody Tells You

Carry cash. A meaningful number of the small stops, especially in Kansas, Oklahoma, and rural Arizona, are cash only or have unreliable card readers.

Fill up when you are at half a tank. The stretch across the Mojave has very long gaps between working stations, and Amboy's fuel availability has come and gone over the years. Half a tank is the trigger, not a quarter.

Cell service disappears. Download offline maps for Arizona and the California desert before you leave Flagstaff.

Check hours the morning of, not the week before. Independent businesses on the route close for family events, weather, and slow seasons. A phone call the same morning saves a 40-mile detour.

Many places close Sunday and Monday. Build your rest days around that rather than fighting it.

Bring a paper map as backup. Not for navigation exactly, but because the route splits and rejoins constantly and a paper overview is faster than pinching a screen.

Watch for the burros in Oatman and drive the switchbacks of Sitgreaves Pass slowly. It is a narrow road with no shoulder and drivers who are looking at the view instead of the lane.

If your trip includes national parks along the way, our national park packing list covers entry passes and what to keep in the car, and the driving vacation planner helps sequence multi-stop routes.

Frequently Asked Questions

How long does it take to drive Route 66?

Two weeks is the standard answer for driving the historic alignments with time to stop. Ten days is possible if you skip detours and accept some interstate. Three weeks lets you add the Santa Fe loop, the Grand Canyon, and unhurried mornings. Driving it purely on interstates takes about four days and misses the point entirely.

Can you still drive the entire original Route 66?

Not as one continuous road. Roughly 85 percent of the original alignments are drivable in some form, but sections have been demolished, absorbed into interstates, or closed. A dedicated Route 66 guidebook or app is what bridges the gaps, since general navigation apps will not follow the old road.

Should I drive Route 66 east to west or west to east?

East to west, Chicago to Santa Monica, for most travelers. The sun sits behind you during morning driving, the historical narrative runs that way, and the Santa Monica Pier is a much better finish line than a Chicago intersection. West to east is perfectly valid if it fits your flights better.

What is the best section if I only have a few days?

Arizona, if you want scenery: Seligman to Oatman is the longest original stretch and the most dramatic. Oklahoma, if you want the most authentic surviving road culture and original pavement. Illinois, if you want museums, easy signage, and the least logistical friction.

Do I need a special vehicle for Route 66?

No. The entire drivable route is paved and any standard car handles it. Comfort matters more than capability, since you will be in the seat for many hours. A car with good air conditioning is genuinely important for the desert legs.

Where should I stay along Route 66?

Mix vintage motels with a few chain nights. The Blue Swallow in Tucumcari, the Wigwam Motels in Holbrook and Rialto, the Boots Court in Carthage, and the Munger Moss in Lebanon are the classic bookings, and the well-known ones need reservations well ahead in peak season.

Is Route 66 worth it with kids?

Yes, with shorter driving days and more stops. The roadside attractions are built for exactly this: giant statues, painted cars you can spray, a whale you can climb, burros that come to the window. Cap driving at about 150 miles a day and the trip works well for younger kids.

The Short Version

Two weeks, east to west, about 175 miles a day, with a Route 66 specific guide because your phone will not find the road for you. Book the two ends and three anchor nights, leave the rest open, carry cash, and fill the tank at half empty once you are west of Albuquerque.

Then pack for eight states of weather in one car. Start your list with the packing list generator, work through the road trip packing list for the front-seat and trunk split, and use our how to plan a road trip guide to pin down the budget and driving-hours math before you book anything.