{"id":198,"date":"2026-09-18T12:20:25","date_gmt":"2026-09-18T12:20:25","guid":{"rendered":"https:\/\/grippedbytravel.com\/?page_id=198"},"modified":"2026-09-18T12:49:54","modified_gmt":"2026-09-18T12:49:54","slug":"14-day-route-66-road-trip-chicago-to-santa-monica","status":"publish","type":"page","link":"https:\/\/grippedbytravel.com\/index.php\/14-day-route-66-road-trip-chicago-to-santa-monica\/","title":{"rendered":"14 day Route 66 Road Trip: Chicago to Santa Monica"},"content":{"rendered":"\n

If you want to experience as much of the original Route 66 as possible<\/strong>, I’d recommend a 14-day road trip<\/strong>. This pace gives you time to drive surviving sections of the historic road, visit classic roadside attractions, and enjoy some of America’s most iconic small towns.<\/p>\n\n\n\n

Day 1: Chicago, Illinois to Springfield, Illinois<\/h4>\n\n\n\n

Mileage:<\/strong> ~200 miles<\/p>\n\n\n\n

Highlights:<\/p>\n\n\n\n

    \n
  • Begin at the historic Route 66 Begin Sign in downtown Chicago<\/li>\n<\/ul>\n\n\n\n
      \n
    • Joliet Area Historical Museum<\/li>\n\n\n\n
    • Gemini Giant in Wilmington<\/li>\n\n\n\n
    • Launching Pad Drive-In<\/li>\n\n\n\n
    • Route 66 Hall of Fame & Museum in Pontiac<\/li>\n\n\n\n
    • Lincoln sites in Springfield<\/li>\n<\/ul>\n\n\n\n

      Overnight: Springfield<\/p>\n\n\n\n

      Day 2: Springfield to St. Louis, Missouri<\/h4>\n\n\n\n

      Mileage:<\/strong> ~115 miles<\/p>\n\n\n\n

      Highlights:<\/p>\n\n\n\n

        \n
      • Cozy Dog Drive-In (claims birthplace of the corn dog on a stick)<\/li>\n\n\n\n
      • Chain of Rocks Bridge over the Mississippi<\/li>\n\n\n\n
      • Explore St. Louis<\/li>\n\n\n\n
      • Gateway Arch<\/li>\n<\/ul>\n\n\n\n

        Overnight: St. Louis<\/p>\n\n\n\n

        Day 3: St. Louis to Springfield, Missouri<\/h4>\n\n\n\n

        Mileage:<\/strong> ~220 miles<\/p>\n\n\n\n

        Highlights:<\/p>\n\n\n\n

          \n
        • Meramec Caverns<\/li>\n\n\n\n
        • Cuba’s Route 66 murals<\/li>\n\n\n\n
        • Devil’s Elbow historic bridge<\/li>\n\n\n\n
        • Red Oak II ghost town<\/li>\n\n\n\n
        • Downtown Springfield, MO<\/li>\n<\/ul>\n\n\n\n

          Overnight: Springfield, MO<\/p>\n\n\n\n

          Day 4: Springfield, Missouri to Tulsa, Oklahoma<\/h4>\n\n\n\n

          Mileage:<\/strong> ~180 miles<\/p>\n\n\n\n

          Highlights:<\/p>\n\n\n\n

            \n
          • Route 66 Car Museum in Carthage<\/li>\n\n\n\n
          • Rainbow Bridge in Kansas<\/li>\n\n\n\n
          • Historic Route 66 through Miami, Oklahoma<\/li>\n\n\n\n
          • Blue Whale of Catoosa<\/li>\n\n\n\n
          • Tulsa’s Art Deco downtown<\/li>\n<\/ul>\n\n\n\n

            Overnight: Tulsa<\/p>\n\n\n\n

            Day 5: Tulsa to Oklahoma City<\/h4>\n\n\n\n

            Mileage:<\/strong> ~110 miles<\/p>\n\n\n\n

            Highlights:<\/p>\n\n\n\n

              \n
            • Route 66 Museum in Clinton<\/li>\n\n\n\n
            • Arcadia Round Barn<\/li>\n\n\n\n
            • Pops 66 Soda Ranch<\/li>\n\n\n\n
            • Historic Bricktown district<\/li>\n<\/ul>\n\n\n\n

              Overnight: Oklahoma City<\/p>\n\n\n\n

              Day 6: Oklahoma City to Amarillo, Texas<\/h4>\n\n\n\n

              Mileage:<\/strong> ~260 miles<\/p>\n\n\n\n

              Highlights:<\/p>\n\n\n\n

                \n
              • Historic Route 66 through Weatherford<\/li>\n\n\n\n
              • Shamrock’s restored Conoco Tower Station<\/li>\n\n\n\n
              • U-Drop Inn Cafe<\/li>\n\n\n\n
              • Cadillac Ranch at Sunset<\/li>\n<\/ul>\n\n\n\n

                Overnight: Amarillo<\/p>\n\n\n\n

                Day 7: Amarillo to Santa Fe, New Mexico<\/h4>\n\n\n\n

                Mileage:<\/strong> ~290 miles<\/p>\n\n\n\n

                Highlights:<\/p>\n\n\n\n

                  \n
                • MidPoint Cafe in Adrian (halfway point of Route 66)<\/li>\n\n\n\n
                • Tucumcari’s neon motel district<\/li>\n\n\n\n
                • Optional original Route 66 alignment to Santa Fe<\/li>\n\n\n\n
                • Plaza and galleries in Santa Fe<\/li>\n<\/ul>\n\n\n\n

                  Overnight: Santa Fe<\/p>\n\n\n\n

                  Day 8: Santa Fe to Albuquerque<\/h4>\n\n\n\n

                  Mileage:<\/strong> ~65 miles<\/p>\n\n\n\n

                  Take a shorter day.<\/p>\n\n\n\n

                  Highlights:<\/p>\n\n\n\n

                    \n
                  • Turquoise Trail scenic route<\/li>\n\n\n\n
                  • Old Town Albuquerque<\/li>\n\n\n\n
                  • Route 66 neon signs<\/li>\n\n\n\n
                  • Indian Pueblo Cultural Center<\/li>\n<\/ul>\n\n\n\n

                    Overnight: Albuquerque<\/p>\n\n\n\n

                    Day 9: Albuquerque to Gallup<\/h4>\n\n\n\n

                    Mileage:<\/strong> ~140 miles<\/p>\n\n\n\n

                    Highlights:<\/p>\n\n\n\n

                      \n
                    • Laguna Pueblo<\/li>\n\n\n\n
                    • Grants mining history<\/li>\n\n\n\n
                    • Continental Divide crossing<\/li>\n\n\n\n
                    • Historic El Rancho Hotel in Gallup<\/li>\n<\/ul>\n\n\n\n

                      Overnight: Gallup<\/p>\n\n\n\n

                      Day 10: Gallup to Holbrook, Arizona<\/h4>\n\n\n\n

                      Mileage:<\/strong> ~95 miles<\/p>\n\n\n\n

                      Highlights:<\/p>\n\n\n\n

                        \n
                      • Petrified Forest National Park<\/li>\n\n\n\n
                      • Painted Desert<\/li>\n\n\n\n
                      • Route alignment through the park<\/li>\n\n\n\n
                      • Wigwam Motel<\/li>\n<\/ul>\n\n\n\n

                        Overnight: Holbrook<\/p>\n\n\n\n

                        Day 11: Holbrook to Williams, Arizona<\/h4>\n\n\n\n

                        Mileage:<\/strong> ~190 miles<\/p>\n\n\n\n

                        Highlights:<\/p>\n\n\n\n

                          \n
                        • Winslow \/ “Standin’ on the Corner” Park<\/li>\n\n\n\n
                        • Meteor Crater<\/li>\n\n\n\n
                        • Flagstaff’s preserved Route 66 district<\/li>\n\n\n\n
                        • Historic Williams<\/li>\n<\/ul>\n\n\n\n

                          Overnight: Williams<\/p>\n\n\n\n

                          Day 12: Grand Canyon Excursion<\/h4>\n\n\n\n

                          Mileage:<\/strong> ~120 miles round trip<\/p>\n\n\n\n

                          Highlights:<\/p>\n\n\n\n

                            \n
                          • Full day at Grand Canyon National Park<\/li>\n\n\n\n
                          • Return to Williams<\/li>\n<\/ul>\n\n\n\n

                            Overnight: Williams<\/p>\n\n\n\n

                            Day 13: Williams to Barstow, California<\/h4>\n\n\n\n

                            Mileage:<\/strong> ~360 miles<\/p>\n\n\n\n

                            Highlights:<\/p>\n\n\n\n

                              \n
                            • Seligman (birthplace of Route 66 preservation)<\/li>\n\n\n\n
                            • Hackberry General Store<\/li>\n\n\n\n
                            • Kingman<\/li>\n\n\n\n
                            • Oatman wild burros<\/li>\n\n\n\n
                            • Mojave Desert crossing<\/li>\n\n\n\n
                            • Barstow Route 66 Museum<\/li>\n<\/ul>\n\n\n\n

                              Overnight: Barstow<\/p>\n\n\n\n

                              Day 14: Barstow to Santa Monica<\/h4>\n\n\n\n

                              Mileage:<\/strong> ~130 miles<\/p>\n\n\n\n

                              Highlights:<\/p>\n\n\n\n

                                \n
                              • Elmer’s Bottle Tree Ranch<\/li>\n\n\n\n
                              • San Bernardino’s McDonald’s Museum site<\/li>\n\n\n\n
                              • Pasadena sections of historic Route 66<\/li>\n\n\n\n
                              • End of the famous Santa Monica Piet “End of the Trail” sign<\/li>\n<\/ul>\n\n\n\n

                                Celebrate with sunset on the Pacific Ocean.<\/p>\n\n\n\n

                                Don’t Miss Top 10 Route 66 Stops<\/h4>\n\n\n\n
                                  \n
                                1. Route 66 Begin Sign, Chicago<\/li>\n\n\n\n
                                2. Chain of Rocks Bridge, Missouri<\/li>\n\n\n\n
                                3. Blue Whale of Catoosa, Oklahoma<\/li>\n\n\n\n
                                4. Cadillac Ranch, Texas<\/li>\n\n\n\n
                                5. MidPoint Cafe, Adrian, Texas<\/li>\n\n\n\n
                                6. Santa Fe Historic Plaza<\/li>\n\n\n\n
                                7. Petrified Forest National Park<\/li>\n\n\n\n
                                8. Wigwam Motel, Holbrook<\/li>\n\n\n\n
                                9. Oatman, Arizona<\/li>\n\n\n\n
                                10. Santa Monica Pier<\/li>\n<\/ol>\n\n\n\n

                                  Total distance:<\/strong> Approximately 2,700-3,000 miles depending on how many original alignments and side trips you include.<\/p>\n\n\n\n

                                  For a true Route 66 enthusiast, I’d also suggest adding a few extra nights in Tulsa, Santa Fe, Williams, and Oatman\/Kingman<\/strong>, as these areas contain some of the best-preserved and most scenic sections of the original road.<\/p>\n","protected":false},"excerpt":{"rendered":"

                                  If you want to experience as much of the original Route 66 as possible, I’d recommend a 14-day road trip. This pace gives you time to drive surviving sections of the historic road, visit classic roadside attractions, and enjoy some of America’s most iconic small towns. Day 1: Chicago, Illinois to Springfield, Illinois Mileage: ~200 […]<\/p>\n","protected":false},"author":1,"featured_media":0,"parent":0,"menu_order":0,"comment_status":"closed","ping_status":"closed","template":"","meta":{"footnotes":""},"class_list":["post-198","page","type-page","status-publish","hentry"],"_links":{"self":[{"href":"https:\/\/grippedbytravel.com\/index.php\/wp-json\/wp\/v2\/pages\/198","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/grippedbytravel.com\/index.php\/wp-json\/wp\/v2\/pages"}],"about":[{"href":"https:\/\/grippedbytravel.com\/index.php\/wp-json\/wp\/v2\/types\/page"}],"author":[{"embeddable":true,"href":"https:\/\/grippedbytravel.com\/index.php\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/grippedbytravel.com\/index.php\/wp-json\/wp\/v2\/comments?post=198"}],"version-history":[{"count":2,"href":"https:\/\/grippedbytravel.com\/index.php\/wp-json\/wp\/v2\/pages\/198\/revisions"}],"predecessor-version":[{"id":204,"href":"https:\/\/grippedbytravel.com\/index.php\/wp-json\/wp\/v2\/pages\/198\/revisions\/204"}],"wp:attachment":[{"href":"https:\/\/grippedbytravel.com\/index.php\/wp-json\/wp\/v2\/media?parent=198"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}