The Ultimate Route 66 2-Week Itinerary: Chicago to Santa Monica, Day by Day

Somewhere between a neon lit motel in New Mexico and a giant blue whale in Oklahoma, Route 66 stops being a road and becomes a story. It’s the original American road trip: eight states, three time zones, and roughly 2,400 miles of diners, drive-ins, desert, and kitsch. And with the highway’s 100th anniversary arriving in November 2026, there has never been a better moment to drive it.

This Route 66 2 week itinerary takes you from Lake Michigan to the Pacific, one realistic driving day at a time. It leaves room for the detours, roadside photo stops, and slow pie breaks that make the trip worth taking.Flying in for the trip? Book a multi-city flight (Fly into Chicago O’Hare and out of Los Angeles LAX) for a seamless road trip experience.

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Route 66 2-Week Itinerary at a Glance

• Start: Chicago, Illinois (Adams Street and Michigan Avenue)
• End: Santa Monica Pier, California
• Total distance: about 2,400 miles of driving along the historic route, plus local driving in cities
• States: Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona, California
• Average driving day: 150-250 miles, or 3-5 hours of actual driving
• Best for: first-time road trippers, couples, friends, and families with older kids

Route 66 2-Week Itinerary: Map, Mileage & Main Stops

Day	Route	Approx. miles	Highlight
1	Chicago (explore)	local	Start-of-route sign, Millennium Park
2	Chicago → Springfield, IL	200	Gemini Giant, Pontiac murals, Cozy Dog
3	Springfield, IL → St. Louis, MO	100	Chain of Rocks Bridge, Gateway Arch
4	St. Louis → Springfield, MO	210	Meramec Caverns, Cuba murals
5	Springfield, MO → Tulsa, OK	185	Galena, KS; Blue Whale of Catoosa
6	Tulsa → Oklahoma City	105	Round Barn, POPS, OKC Memorial
7	Oklahoma City → Amarillo, TX	260	Route 66 Museums, Cadillac Ranch
8	Amarillo → Tucumcari, NM	110	Midpoint Café, Blue Swallow Motel
9	Tucumcari → Albuquerque	175	Blue Hole, Nob Hill neon
10	Albuquerque → Gallup	140	Acoma Pueblo, El Rancho Hotel
11	Gallup → Flagstaff, AZ	190	Petrified Forest, Winslow, Wigwam Motel
12	Flagstaff → Kingman	150	Williams, Seligman, Hackberry
13	Kingman → Barstow, CA	220	Oatman burros, Amboy Crater, Mojave
14	Barstow → Santa Monica	150	Cajon Pass, Pasadena, the Pier

Mileages are approximate and vary with the alignments you choose.

What to Know Before Driving Route 66

Route 66 isn’t one road you can follow in a straight line. It was officially decommissioned in 1985, and much of it was absorbed into interstates (I-55, I-44, I-40, and I-15 among them). What remains is a patchwork of frontage roads, state highways, and city streets. That’s part of the fun, and also the reason a little planning pays off.

How Long Does It Take to Drive Route 66?

You could technically drive it in 7-10 days, but you’d spend most of it behind the wheel. Two weeks is the sweet spot: enough time for 3-4 hours of driving a day, a full day to enjoy Chicago, and time for the museums, motels, and detours that define the trip. Three weeks is lovely if you have it.

When Is the Best Time to Drive Route 66?

• Spring (April-May): mild temperatures and blooming desert, with fewer crowds before summer.
• Fall (September-October): warm days, golden light, and comfortable desert driving.
• Summer: peak season, but the Mojave and Arizona can be punishingly hot, and some outdoor stops become uncomfortable by midday.
• Winter: snow and ice are real risks in Flagstaff, Albuquerque, and the Texas Panhandle, and some small businesses close seasonally.

How to Navigate Historic Route 66

• Look for brown “Historic Route 66” signs, but don’t rely on them. They disappear without warning.
• Use a dedicated turn-by-turn guide, such as Jerry McClanahan’s EZ66 Guide, or state Route 66 association maps.
• Download offline maps before you leave. Cell service is spotty in the Mojave and across northern Arizona.Get a USA Unlimited eSIM for GPS → Buy USA Travel eSIM Online
• Mark your lodging and gas stops in advance, since some desert stretches have 50+ miles between services.
  

The Complete 14-Day Route 66 Road Trip Itinerary

Day 1: Explore Chicago, Illinois

Start the way every Route 66 traveler does: at the “Begin Route 66” sign on Adams Street, near Michigan Avenue. Fuel up with a classic breakfast at Lou Mitchell’s, a Route 66 institution near Union Station. Spend the day on Millennium Park‘s Cloud Gate (“the Bean”), the Art Institute of Chicago, and the riverfront. Pick up your rental car now if you haven’t already, and get an early night.Check Rental Car Prices from Chicago to LA

Day 2: Chicago to Springfield, Illinois (about 200 miles)

Head southwest through small town Illinois. Highlights:

• Joliet: Route 66 Park and the old prison.
• Wilmington: the towering Gemini Giant “Muffler Man.”
• Pontiac: a Route 66 museum and cheerful murals.
• Funks Grove: local maple sirup, made on-site.
• Litchfield: the Ariston Café, a Route 66 dining landmark since the 1930s.

End in Springfield and grab a Cozy Dog at the Cozy Dog Drive In, famous for its corn dogs on a stick.

Day 3: Springfield, Illinois, to St. Louis, Missouri (about 100 miles)

A short driving day gives you time for Springfield’s Lincoln sites (his home, the museum, and his tomb) before crossing the Mississippi. In the St. Louis area, walk the Chain of Rocks Bridge, the old Route 66 river crossing with its famous bend, then head downtown to the Gateway Arch. Finish with frozen custard at Ted Drewes, a long time local favorite.

Day 4: St. Louis to Springfield, Missouri (about 210 miles)

The Missouri Ozarks bring rolling hills and some of the best preserved stretches of the old road:

• Meramec Caverns: a classic roadside cave attraction.
• Cuba: a town known for its large Route 66 murals.
• Devil’s Elbow: a scenic bend along the Big Piney River.

Springfield, Missouri, calls itself the “Birthplace of Route 66,” since the road was formally proposed here in 1926.

Day 5: Springfield, Missouri, to Tulsa, Oklahoma (about 185 miles)

• Carthage: the Boots Motel and neon lit streets.
• Kansas (about 13 miles): only a tiny slice of Route 66 crosses Kansas. Stop in Galena for Cars on the Route, the old gas station that inspired a character in Pixar’s Cars, and the Rainbow Bridge near Riverton.
• Catoosa, Oklahoma: the beloved Blue Whale of Catoosa, a quirky swimming-hole landmark.
• Tulsa: the Cyrus Avery Route 66 Memorial Bridge, the Golden Driller statue, and the Meadow Gold sign.

Day 6: Tulsa to Oklahoma City (about 105 miles)

Another short day, with plenty to see. Stop at the Round Barn in Arcadia and POPS 66 Soda Ranch, which has hundreds of soda flavors. In Oklahoma City, visit the Oklahoma City National Memorial & Museum for a sobering and well-designed stop. Then explore the Plaza District and Bricktown for dinner.

Day 7: Oklahoma City to Amarillo, Texas (about 260 miles)

This is your longest driving day, so start early.

• Clinton: the Oklahoma Route 66 Museum.
• Hydro: Lucille’s Service Station, a classic gas stop.
• Elk City: the National Route 66 & Transportation Museum.
• Amarillo: the graffiti-covered Cadillac Ranch at sunset and dinner at The Big Texan Steak Ranch, home of the 72-ounce steak challenge.

Day 8: Amarillo to Tucumcari, New Mexico (about 110 miles)

Roll through the Texas Panhandle to Adrian, home of the Midpoint Café, the halfway point of Route 66 between Chicago and Los Angeles. Cross into New Mexico and arrive in Tucumcari, a town built on neon. Check into the Blue Swallow Motel, one of the most photographed motels on the route, and walk the main drag after dark.

Day 9: Tucumcari to Albuquerque, New Mexico (about 175 miles)

Break up the drive at the Blue Hole in Santa Rosa, a clear artesian swimming spot popular with divers. In Albuquerque, cruise Central Avenue, which follows Route 66 through the city, and wander Nob Hill’s neon signs. Visit Old Town for adobe architecture and local green-chile cooking.

Day 10: Albuquerque to Gallup, New Mexico (about 140 miles)

Visit Petroglyph National Monument in the morning. If you want a cultural stop, Acoma Pueblo (“Sky City”) offers guided tours of one of the oldest continuously inhabited communities in the U.S. (check tour availability in advance). Then continue to Gallup and stay at the historic El Rancho Hotel, where Hollywood stars once slept.

Day 11: Gallup to Flagstaff, Arizona (about 190 miles)

This is one of the most scenic days. Drive through Petrified Forest National Park and the Painted Desert, then stop in Holbrook to sleep in a concrete teepee at the Wigwam Motel (or just photograph it). In Winslow, stand on the corner made famous by the Eagles at Standin’ on the Corner Park. If time allows, see Meteor Crater east of Flagstaff. End the day in Flagstaff, a cool mountain town with excellent food.

Day 12: Flagstaff to Kingman, Arizona (about 150 miles)

Here you get the longest uninterrupted stretch of old Route 66.

• Williams: a charming Route 66 town and gateway to the Grand Canyon.
• Seligman: home of the Delgadillo family’s Snow Cap Drive-In, full of cheerful gags and jokes.
• Hackberry General Store: a retro-Americana photo stop.
• Kingman: a small museum and a handy overnight base.

Day 13: Kingman to Barstow, California (about 220 miles)

Take the winding road to Oatman, where wild burros wander the main street (be sure to follow posted rules on feeding them), then cross the Colorado River into California. In the Mojave Desert, stop at Amboy for Roy’s Motel & Café sign and the nearby Amboy Crater. Roll into Barstow and visit the Route 66 Mother Road Museum. If you have time, Bagdad Café in Newberry Springs is a popular detour.

Day 14: Barstow to Santa Monica, California (about 150 miles)

The finish line. Cross Cajon Pass, drive through the San Bernardino Valley (look for the Wigwam Motel in Rialto), pass the Colorado Street Bridge in Pasadena, and then follow Santa Monica Boulevard toward the coast. Finish at the Santa Monica Pier and the “End of the Trail” sign. Take the photo, dip your feet in the Pacific, and toast the trip.

How Much Does a 2-Week Route 66 Road Trip Cost?

Costs vary widely with season, car, and how many people share them. These are rough planning ranges, so check current prices before you book.

Rental Car, Fuel, Accommodation & Food

• Rental car: a one-way rental from Chicago to Los Angeles often carries a one-way drop fee, so compare companies carefully. Book early, especially around the centennial.
• Fuel: at roughly 2,400 miles and about 25-30 mpg, plan on 80-100 gallons. Multiply by current gas prices for your estimate.
• Accommodation: budget roughly $90-$180 per night for mid-range motels and hotels. Iconic stays like the Blue Swallow can sell out months ahead.Find & Book Route 66 Motels → Check Motels in Tucumcari
• Food: about $50-$90 per person per day for diners, drive-ins, and the occasional splurge.
• Attractions: most roadside stops are free. Budget for a few museums, cave tours, and national park entry fees.
  Compare One-Way Car Rental Deals
• Check Rental Car Prices from Chicago to LA

Practical Ways to Save Money on Route 66

• Book lodging early and use free cancellation where possible.
• Split rooms and fuel costs with friends or family.
• Eat the big meal at lunch, since diners often have cheaper lunch menus.
• Pick up an America the Beautiful pass if you’ll visit several national parks.
• Fill up in larger towns, because rural gas can cost more.

Best Stops and Attractions Along Route 66

Historic Landmarks and Classic Roadside Attractions

• Gemini Giant (Wilmington, IL)
• Chain of Rocks Bridge (St. Louis, MO)
• Blue Whale of Catoosa (OK)
• Cadillac Ranch (Amarillo, TX)
• Midpoint Café (Adrian, TX)
• Blue Swallow Motel (Tucumcari, NM)
• Wigwam Motel (Holbrook, AZ)
• Hackberry General Store (AZ)
• Santa Monica Pier (CA)

Optional Detours Worth Considering

• Grand Canyon: about an hour from Williams, AZ. Worth the extra night if you can spare it.
• Santa Fe, NM: the pre-1937 alignment passed through Santa Fe, adding a scenic loop and great food.
• Meramec State Park and Ozark caves
• Joplin and Carthage, MO for extra Route 66 history.

What to Pack for a Route 66 Road Trip

• Layers: desert days can be hot, mountain nights can be cold.
• Sunscreen, sunglasses, and a hat.
• A reusable water bottle, a cooler, and snacks.
• Phone mount, car charger, and offline maps or a printed guide.
• Cash for small-town spots that don’t take cards.
• Comfortable shoes for roadside stops and museums.
• A small first-aid kit and emergency supplies for desert stretches.
• A notebook or camera, since you’ll want to remember it.

Frequently Asked Questions About Route 66

Is Two Weeks Enough to Drive Route 66?

Yes. Two weeks lets you drive the full route from Chicago to Santa Monica with time for the best stops and a day in Chicago. Fewer than 10 days works, but you’ll mostly be driving.

Can You Drive the Entire Historic Route 66?

Mostly. About 85% of the original road is still drivable, though some sections are gravel, closed, or replaced by interstates. Plan around a good guidebook or app, and be flexible.

Where Does Route 66 Start and End?

It officially starts in Chicago, Illinois, near Adams Street and Michigan Avenue, and ends in Santa Monica, California, at the Santa Monica Pier.

Final Tips for Planning Your Route 66 Adventure

• Book key lodging early, especially for the Blue Swallow and other classic motels.
• Leave margin in your schedule. The best Route 66 moments are unplanned.
• Check hours before you go, since many small businesses keep limited or seasonal schedules.
• Talk to locals. They know which diner has the best pie.
• Fill up on gas whenever you’re below half a tank in the desert.

Following this Route 66 2-week itinerary can help you experience the highlights of America’s Mother Road in 14 days. Plan your overnight stops in advance, allow time for roadside attractions, and keep your schedule flexible so you can enjoy the journey from Chicago to Santa Monica.