Route 66 itinerary for 2 weeks: Chicago to Santa Monica in the centennial year

Route Chicago, Illinois → Santa Monica, California

Distance 2,400 miles

Estimated fuel $353

A 14-day Route 66 itinerary from Chicago to Santa Monica for the 2026-27 centennial, with nightly stops by state, a cost estimate and what recent drivers report.

Two weeks is the right amount of time for a Route 66 itinerary from Chicago to Santa Monica. Fourteen days lets you follow the old road through all eight states, keep most driving days to three or four hours, and still stop for the diners, motels and roadside oddities that make the trip. Plan on 2,300 to 2,450 miles, depending on which alignments you follow. The official Route 66 Centennial marks the highway's 100th birthday on November 11, 2026, so expect more events, more travelers and fuller historic motels through the centennial season. Below is a day-by-day plan with overnight stops, a cost estimate and what recent drivers say about doing it.

Route 66 at a glance

Item	Detail
Start and end	Adams Street, Chicago, to the "End of the Trail" sign on Santa Monica Pier
Distance	About 2,400 miles (the 1926-era road was about 2,448 miles; today's drivable route is shorter)
States	Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona, California
Recommended time	14 days minimum, 3 weeks if you can
Best seasons	Late April to June and September to October
Navigation	A dedicated turn-by-turn guide such as the EZ66 Guide for Travelers, plus offline maps

Route 66 was decommissioned as a federal highway in 1985, according to the National Park Service Route 66 Corridor Preservation Program. It survives as a patchwork of state roads, frontage roads, city streets and interstate, and it is not signed consistently. That is why almost every experienced driver recommends a printed mile-by-mile guide.

How long does it take to drive Route 66?

You could cover the distance on the interstates in four or five long days, but you would see very little of Route 66. Across 14 days you average roughly 170 miles a day, which on two-lane roads at 45 to 55 mph works out to three to four hours behind the wheel, before stops. With 10 days or fewer, pick one or two sections (Illinois and Missouri, or New Mexico and Arizona) and use I-44 and I-40 to cover the rest.

2-week Route 66 itinerary, day by day

Day 1: Chicago to Springfield, Illinois (about 200 miles)

Start at the "Begin Historic Route 66" sign on Adams Street, then head southwest through Joliet to the Gemini Giant in Wilmington, the Route 66 museum and murals in Pontiac, and the small towns of Atlanta and Lincoln. Sleep in Springfield, the state capital, where Lincoln sites sit alongside Route 66 diners.

Day 2: Springfield to Cuba or Rolla, Missouri (about 210 miles)

Cross the Mississippi near the old Chain of Rocks Bridge (now pedestrian only), pass through St. Louis, and pick up the road west on old alignments beside I-44. Cuba's murals and the Wagon Wheel Motel make a good overnight stop.

Day 3: Rolla to Carthage, Missouri (about 200 miles)

Drive the Devil's Elbow section through the Ozarks, then pass through Springfield, Missouri, often called the birthplace of Route 66. Overnight at Carthage, home of the restored Boots Court motel.

Day 4: Carthage to Tulsa, Oklahoma (about 150 miles)

Kansas has only about 13 miles of the route, but Galena and Baxter Springs pack a lot in. Cross into Oklahoma through Commerce and Miami, then stop at the Blue Whale of Catoosa before Tulsa. If you are on the road on November 11, Tulsa is one of the cities planning birthday events; check the official Oklahoma events calendar.

Day 5: Tulsa to Clinton, Oklahoma (about 190 miles)

Take the old road through Sapulpa, Stroud and Chandler to the Round Barn and Pops in Arcadia, then cross Oklahoma City. The Oklahoma Route 66 Museum in Clinton is one of the best on the route.

Day 6: Clinton to Amarillo, Texas (about 180 miles)

Cross into the Texas Panhandle at Texola, stop at the art deco U-Drop Inn in Shamrock and the leaning water tower near Groom, and finish with Cadillac Ranch on the west side of Amarillo.

Day 7: Amarillo to Tucumcari, New Mexico (about 115 miles)

A short day. Stop at the Midpoint Cafe in Adrian, roughly halfway between Chicago and Los Angeles, and the ghost town of Glenrio on the state line. Tucumcari's neon is the reason to arrive before dark; the Blue Swallow Motel is the classic stay.

Day 8: Tucumcari to Albuquerque (about 175 miles, more via Santa Fe)

Swim or look into the Blue Hole in Santa Rosa, then choose between the direct post-1937 road to Albuquerque or the older loop north through Santa Fe, which adds roughly 60 miles and a lot of climbing. Albuquerque's Central Avenue is the longest urban stretch of Route 66 still lined with motor courts.

Day 9: Albuquerque to Gallup (about 140 miles)

Head west past Laguna Pueblo and Grants. Acoma Pueblo's Sky City is a worthwhile detour. In Gallup, the El Rancho Hotel trades on its Hollywood past.

Day 10: Gallup to Holbrook, Arizona (about 95 miles)

Petrified Forest National Park is the only national park that preserves a section of the Route 66 alignment, and it is worth half a day. Check the park's fees page before you go. Sleep in a concrete teepee at the Wigwam Motel in Holbrook.

Day 11: Holbrook to Flagstaff (about 90 miles)

Stand on the corner in Winslow, then visit Meteor Crater before climbing to Flagstaff at about 7,000 feet. If the Grand Canyon is on your list, add a day here; it is a long detour north from Flagstaff or Williams.

Day 12: Flagstaff to Kingman (about 150 miles)

Williams is the last town I-40 bypassed. West of Ash Fork, leave the interstate for the longest unbroken stretch of old Route 66, through Seligman, Peach Springs and Hackberry to Kingman.

Day 13: Kingman to Barstow, California (about 210 miles)

Climb the switchbacks over Sitgreaves Pass to Oatman and its wandering burros, then drop to the Colorado River at Topock and Needles. The Mojave stretch past Amboy and Roy's is remote, and parts of the National Trails Highway have had bridge-repair closures in recent years, so check San Bernardino County road status and carry water. Sleep in Barstow.

Day 14: Barstow to Santa Monica (about 140 miles)

Drive through Victorville and over Cajon Pass to San Bernardino, then along Foothill Boulevard and through Pasadena, finishing on Santa Monica Boulevard at the pier. From there, the Pacific Coast Highway road trip is the obvious next chapter.

Route 66 road trip cost (estimate for two people)

Item	Estimate	Notes
Fuel	About $353	2,400 miles at 28 MPG and the AAA national average of $4.12 a gallon (Nov 4, 2026). Illinois was averaging $4.64 the same day, and California usually runs higher.
Lodging (13 nights)	$1,400-2,600	Historic motels and mid-range chains; centennial-season weekends cost more
Food	$1,000-1,700	Roughly $70-120 a day for two
Attractions and parks	$150-300	Museums, Meteor Crater, Petrified Forest
One-way rental drop fee	Varies widely	Get quotes from several companies; Chicago to Los Angeles one-way fees can be significant

All figures are estimates; prices change, especially fuel. Driving electric instead? See the Route 66 EV charging guide, which maps fast chargers state by state and compares the cost with gas.

Centennial-year planning tips

Book the icons early. The Blue Swallow, Boots Court, the Wigwam and El Rancho have limited rooms, and centennial events are filling them.
Check the official calendar. The Route 66 Centennial events calendar lists events by state. Time a night around one if you can, and avoid being surprised by road closures for parades.
Collect stamps. The National Park Service has a Route 66 Centennial passport stamp and rack card at sites along the road.
Avoid winter for the full drive. From November to March, snow and ice are possible from Chicago to Flagstaff, and many small museums and businesses cut hours or close.

What people who've done it say

Time is everything. A Wisconsin driver in an August 2026 Tripadvisor thread took three weeks and stopped wherever they liked. Their summary of faster trips: "Some people do it in three days which means they drove it but didn't see it."
The road keeps changing. The same driver reported that the Rabbit Ranch in Illinois no longer operates as an attraction, though much of it is still standing, while newer stops such as Route 66 Motorheads in Springfield, Illinois, have opened. Both they and another forum regular recommended the EZ66 Guide for Travelers for staying on the route. Another regular pointed out that many people who say they are "doing Route 66" are really driving only part of it.
Cap your driving hours. The travel couple behind Independent Travel Cats' 2-week Route 66 itinerary suggest no more than four to five hours of driving a day. They call two weeks a sensible minimum and say that with under 10 days you should drive sections, not the whole thing. They also warn against a winter drive because of snow around Flagstaff and seasonal closures.
Some original alignments are still gravel. A New Zealand motoring writer who drove the full route in an EV in September and October 2024 reported that some original segments are still dirt or gravel. These are optional, but the sports cars on their tour came back feeling rattled. Their hardest day was the final run from Laughlin to Pasadena, which ended three hours behind schedule because of a faulty charger, traffic and sun glare.

Common mistakes

Trusting your phone's default route. Navigation apps will put you on I-44 and I-40. Use a turn-by-turn Route 66 guide and download offline maps for New Mexico, Arizona and the Mojave, where signal drops.
Underestimating the West. The days look short on paper, but heat, altitude and long gaps between services add up. Fill up in Kingman and Needles before the Mojave, and carry water.
Skipping the rental fine print. One-way drop fees and mileage caps vary a lot between companies. Confirm unlimited mileage, and take photos of the car at pickup. A dash cam is also handy for capturing the road itself.
Arriving after dark everywhere. Tucumcari, Albuquerque and Kingman are at their best when the neon is lit, but rural two-lane stretches with wildlife are not where you want to be at night.
Trying to see everything. There are hundreds of stops. Choose the ones that matter to you and leave slack for detours.

Bottom line

A two-week Route 66 itinerary is the minimum that does the road justice: about 2,400 miles, eight states and 13 nights, at three to four hours of driving a day. Book the famous motels early, carry a mile-by-mile guide, plan the western days around fuel and heat, and check the centennial calendar for events near your dates. If you can stretch to three weeks, take the extra time; nobody who did the trip slowly says they wish they had rushed.