{"id":214,"date":"2026-09-18T12:20:13","date_gmt":"2026-09-18T12:20:13","guid":{"rendered":"https:\/\/grippedbytravel.co.uk\/?page_id=214"},"modified":"2026-09-18T12:41:51","modified_gmt":"2026-09-18T12:41:51","slug":"14-day-route-66-road-trip-chicago-to-santa-monica","status":"publish","type":"page","link":"https:\/\/grippedbytravel.co.uk\/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

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

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

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

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

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

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

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

                \"\"
                Cadillac Ranch<\/figcaption><\/figure>\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

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

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

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

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

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

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

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

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

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

                                \"End
                                End of the Trail – Santa Monica<\/figcaption><\/figure>\n\n\n\n

                                Don’t Miss Top 10 Route 66 Stops<\/h4>\n\n\n\n
                                1. Route 66 Begin Sign, Chicago<\/li>
                                2. Chain of Rocks Bridge, Missouri<\/li>
                                3. Blue Whale of Catoosa, Oklahoma<\/li>
                                4. Cadillac Ranch, Texas<\/li>
                                5. MidPoint Cafe, Adrian, Texas<\/li>
                                6. Santa Fe Historic Plaza<\/li>
                                7. Petrified Forest National Park<\/li>
                                8. Wigwam Motel, Holbrook<\/li>
                                9. Oatman, Arizona<\/li>
                                10. Santa Monica Pier<\/li><\/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":[],"_links":{"self":[{"href":"https:\/\/grippedbytravel.co.uk\/index.php\/wp-json\/wp\/v2\/pages\/214"}],"collection":[{"href":"https:\/\/grippedbytravel.co.uk\/index.php\/wp-json\/wp\/v2\/pages"}],"about":[{"href":"https:\/\/grippedbytravel.co.uk\/index.php\/wp-json\/wp\/v2\/types\/page"}],"author":[{"embeddable":true,"href":"https:\/\/grippedbytravel.co.uk\/index.php\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/grippedbytravel.co.uk\/index.php\/wp-json\/wp\/v2\/comments?post=214"}],"version-history":[{"count":3,"href":"https:\/\/grippedbytravel.co.uk\/index.php\/wp-json\/wp\/v2\/pages\/214\/revisions"}],"predecessor-version":[{"id":225,"href":"https:\/\/grippedbytravel.co.uk\/index.php\/wp-json\/wp\/v2\/pages\/214\/revisions\/225"}],"wp:attachment":[{"href":"https:\/\/grippedbytravel.co.uk\/index.php\/wp-json\/wp\/v2\/media?parent=214"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}