14-day itinerary · Road-trip enthusiasts celebrating the Route 66 Centennial across 8 states from Lake Michigan to the Pacific Ocean

14 Days on Historic Route 66: Chicago, St. Louis, Oklahoma, Santa Fe, Grand Canyon & Santa Monica

Follow the historic neon diners, giant roadside murals, Pueblo adobe plazas, and desert canyons along America's most famous highway from Chicago to Santa Monica Pier.

Last reviewed: · Prices in US Dollars ($ USD) are approximate and for orientation only.

Route at a glance

Follow the historic neon diners, giant roadside murals, Pueblo adobe plazas, and desert canyons along America's most famous highway from Chicago to Santa Monica Pier.

Estimated per-person budget ($2,850 – $4,600) covers mid-range hotels, intercity transport, timed attraction or national park passes ($80 America the Beautiful Pass), and daily dining including state sales tax and tip.

Length14 days
Best forRoad-trip enthusiasts celebrating the Route 66 Centennial across 8 states from Lake Michigan to the Pacific Ocean
BasesChicago, St. Louis, Oklahoma, Santa Fe, Grand Canyon & Santa Monica
PaceThe Mother Road cross-country American odyssey (2,448 miles)

Day-by-day plan

Day 1

Chicago: Route 66 Begin Sign (Adams & Michigan), River Cruise & Millennium Park

Snap a photo at the official Route 66 Begin sign across from the Art Institute of Chicago and take an architecture river cruise.

Day 2

Chicago to Springfield, Illinois (200 mi): Pontiac Museum & Lincoln Sites

Stop at the Route 66 Hall of Fame in Pontiac, Cozy Dog Drive In, and Abraham Lincoln's home in Springfield.

Day 3

Springfield to St. Louis, Missouri (100 mi): Chain of Rocks Bridge & Gateway Arch

Walk across the historic 22-degree bend of the Old Chain of Rocks Bridge over the Mississippi River and ride the tram to the top of the 630-foot Gateway Arch.

Day 4

St. Louis through the Ozarks to Springfield, Missouri & Tulsa, Oklahoma

Follow scenic Meramec Caverns and rural Missouri alignments to Tulsa's Art Deco downtown and Buck Atom's Cosmic Curios.

Day 5

Tulsa & Oklahoma City to Clinton, Oklahoma (Route 66 Museum)

Visit Arcadia's Round Barn (1898), Pops 66 Soda Ranch, and the flagship Oklahoma Route 66 Museum in Clinton.

Day 6

Texas Panhandle (Amarillo & Cadillac Ranch) to Tucumcari, New Mexico

See the Conoco Tower Station in Shamrock, spray-paint the half-buried fins at Cadillac Ranch, and photograph the Blue Swallow Motel neon in Tucumcari.

Day 7

Santa Rosa Blue Hole to Santa Fe, New Mexico (Historic Pre-1937 Loop)

Follow the original 1926 alignment north into Santa Fe (7,199 ft) for the 1610 Palace of the Governors, Canyon Road galleries, and red-and-green-chile New Mexican dining.

Day 8

Santa Fe, Bandelier / Taos Pueblo & Albuquerque Central Avenue

Explore ancestral Pueblo cliff dwellings or Taos Pueblo (UNESCO) before cruising neon-lit Central Avenue in Albuquerque.

Day 9

Acoma Sky City, Gallup & Petrified Forest / Painted Desert to Holbrook, Arizona

Drive through Petrified Forest National Park—the only national park containing a preserved segment of Historic Route 66—and see the Wigwam Motel in Holbrook.

Day 10

Winslow ('Standin' on the Corner'), Meteor Crater & Flagstaff to Grand Canyon South Rim

Stop in Winslow and Lowell Observatory in Flagstaff before watching sunset over the Grand Canyon.

Day 11

Grand Canyon Full Day & Historic Williams

Hike along the South Rim, visit Desert View Watchtower, and spend the evening among neon signs in Williams.

Day 12

Seligman (Angel Delgadillo's Barber Shop), Hackberry General Store & Oatman to Kingman/Needles

Drive the longest continuous surviving stretch of original Route 66 (159 miles) past wild burros in the gold-mining town of Oatman.

Day 13

Mojave Desert (Roy's Motel & Café in Amboy, Elmer's Bottle Tree Ranch) to Pasadena

Cross the Mojave National Preserve and Cajon Pass onto Colorado Boulevard in Pasadena.

Day 14

Hollywood Boulevard & Santa Monica Boulevard to the 'End of the Trail' Sign on Santa Monica Pier

Follow Santa Monica Boulevard to the Pacific Ocean, take your finish-line photo on Santa Monica Pier, and celebrate at sunset.

Transport, driving & pass notes

Designed for the mother road cross-country american odyssey (2,448 miles) travel. Compare train, flight, and road-trip costs in USD ($) using our Amtrak & Rail Pass Calculator, $80 National Parks Pass Calculator, and US Trip Budget Calculator.

What to book ahead

  • Apply for your $21 ESTA at esta.cbp.dhs.gov at least 72 hours before departure (or verify visa validity).
  • Book Amtrak Acela / Northeast Regional tickets or rental cars 4–8 weeks ahead for the lowest USD ($) rates.
  • Reserve timed-entry slots for high-demand sights (Statue of Liberty Crown/Pedestal, Alcatraz, Capitol/White House tours, or Recreation.gov park entries) 30–90 days out.

Ways to adapt this route

  • Add 1–2 buffer days if traveling during summer peak or Thanksgiving/Christmas holiday weeks.
  • Use our interactive Itinerary Builder to customize stops and print your day-by-day plan.