{"id":1677,"date":"2026-09-18T10:27:17","date_gmt":"2026-09-18T10:27:17","guid":{"rendered":"https:\/\/travellogs.co.uk\/wordpress\/?page_id=1677"},"modified":"2026-09-18T12:51:12","modified_gmt":"2026-09-18T12:51:12","slug":"14-day-route-66-road-trip-chicago-to-santa-monica","status":"publish","type":"page","link":"https:\/\/travellogs.co.uk\/wordpress\/?page_id=1677","title":{"rendered":"14 day Route 66 Road Trip: Chicago to Santa Monica"},"content":{"rendered":"\n<p class=\"wp-block-paragraph\">If you want to experience <strong>as much of the original Route 66 as possible<\/strong>, I&#8217;d recommend a <strong>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&#8217;s most iconic small towns.<\/p>\n\n\n\n<h4 class=\"wp-block-heading\">Day 1: Chicago, Illinois to Springfield, Illinois<\/h4>\n\n\n\n<p class=\"wp-block-paragraph\"><strong>Mileage:<\/strong> ~200 miles<\/p>\n\n\n\n<p class=\"wp-block-paragraph\">Highlights:<\/p>\n\n\n\n<ul class=\"wp-block-list\">\n<li>Begin at the historic Route 66 Begin Sign in downtown Chicago<\/li>\n\n\n\n<li>Joliet Area Historical Museum<\/li>\n\n\n\n<li>Gemini Giant in Wilmington<\/li>\n\n\n\n<li>Launching Pad Drive-In<\/li>\n\n\n\n<li>Route 66 Hall of Fame &amp; Museum in Pontiac<\/li>\n\n\n\n<li>Lincoln sites in Springfield<\/li>\n<\/ul>\n\n\n\n<p class=\"wp-block-paragraph\">Overnight: Springfield<\/p>\n\n\n\n<h4 class=\"wp-block-heading\">Day 2: Springfield to St. Louis, Missouri<\/h4>\n\n\n\n<p class=\"wp-block-paragraph\"><strong>Mileage:<\/strong> ~115 miles<\/p>\n\n\n\n<p class=\"wp-block-paragraph\">Highlights:<\/p>\n\n\n\n<ul class=\"wp-block-list\">\n<li>Cozy Dog Drive-In (claims birthplace of the corn dog on a stick)<\/li>\n\n\n\n<li>Chain of Rocks Bridge over the Mississippi<\/li>\n\n\n\n<li>Explore St. Louis<\/li>\n\n\n\n<li>Gateway Arch<\/li>\n<\/ul>\n\n\n\n<p class=\"wp-block-paragraph\">Overnight: St. Louis<\/p>\n\n\n\n<h4 class=\"wp-block-heading\">Day 3: St. Louis to Springfield, Missouri<\/h4>\n\n\n\n<p class=\"wp-block-paragraph\"><strong>Mileage:<\/strong> ~220 miles<\/p>\n\n\n\n<p class=\"wp-block-paragraph\">Highlights:<\/p>\n\n\n\n<ul class=\"wp-block-list\">\n<li>Meramec Caverns<\/li>\n\n\n\n<li>Cuba&#8217;s Route 66 murals<\/li>\n\n\n\n<li>Devil&#8217;s Elbow historic bridge<\/li>\n\n\n\n<li>Red Oak II ghost town<\/li>\n\n\n\n<li>Downtown Springfield, MO<\/li>\n<\/ul>\n\n\n\n<p class=\"wp-block-paragraph\">Overnight: Springfield, MO<\/p>\n\n\n\n<h4 class=\"wp-block-heading\">Day 4: Springfield, Missouri to Tulsa, Oklahoma<\/h4>\n\n\n\n<p class=\"wp-block-paragraph\"><strong>Mileage:<\/strong> ~180 miles<\/p>\n\n\n\n<p class=\"wp-block-paragraph\">Highlights:<\/p>\n\n\n\n<ul class=\"wp-block-list\">\n<li>Route 66 Car Museum in Carthage<\/li>\n\n\n\n<li>Rainbow Bridge in Kansas<\/li>\n\n\n\n<li>Historic Route 66 through Miami, Oklahoma<\/li>\n\n\n\n<li>Blue Whale of Catoosa<\/li>\n\n\n\n<li>Tulsa&#8217;s Art Deco downtown<\/li>\n<\/ul>\n\n\n\n<p class=\"wp-block-paragraph\">Overnight: Tulsa<\/p>\n\n\n\n<h4 class=\"wp-block-heading\">Day 5: Tulsa to Oklahoma City<\/h4>\n\n\n\n<p class=\"wp-block-paragraph\"><strong>Mileage:<\/strong> ~110 miles<\/p>\n\n\n\n<p class=\"wp-block-paragraph\">Highlights:<\/p>\n\n\n\n<ul class=\"wp-block-list\">\n<li>Route 66 Museum in Clinton<\/li>\n\n\n\n<li>Arcadia Round Barn<\/li>\n\n\n\n<li>Pops 66 Soda Ranch<\/li>\n\n\n\n<li>Historic Bricktown district<\/li>\n<\/ul>\n\n\n\n<p class=\"wp-block-paragraph\">Overnight: Oklahoma City<\/p>\n\n\n\n<h4 class=\"wp-block-heading\">Day 6: Oklahoma City to Amarillo, Texas<\/h4>\n\n\n\n<p class=\"wp-block-paragraph\"><strong>Mileage:<\/strong> ~260 miles<\/p>\n\n\n\n<p class=\"wp-block-paragraph\">Highlights:<\/p>\n\n\n\n<ul class=\"wp-block-list\">\n<li>Historic Route 66 through Weatherford<\/li>\n\n\n\n<li>Shamrock&#8217;s restored Conoco Tower Station<\/li>\n\n\n\n<li>U-Drop Inn Caf\u00e9<\/li>\n\n\n\n<li>Cadillac Ranch at sunset<\/li>\n<\/ul>\n\n\n\n<p class=\"wp-block-paragraph\">Overnight: Amarillo<\/p>\n\n\n\n<h4 class=\"wp-block-heading\">Day 7: Amarillo to Santa Fe, New Mexico<\/h4>\n\n\n\n<p class=\"wp-block-paragraph\"><strong>Mileage:<\/strong> ~290 miles<\/p>\n\n\n\n<p class=\"wp-block-paragraph\">Highlights:<\/p>\n\n\n\n<ul class=\"wp-block-list\">\n<li>MidPoint Caf\u00e9 in Adrian (halfway point of Route 66)<\/li>\n\n\n\n<li>Tucumcari&#8217;s neon motel district<\/li>\n\n\n\n<li>Optional original Route 66 alignment to Santa Fe<\/li>\n\n\n\n<li>Plaza and galleries in Santa Fe<\/li>\n<\/ul>\n\n\n\n<p class=\"wp-block-paragraph\">Overnight: Santa Fe<\/p>\n\n\n\n<h4 class=\"wp-block-heading\">Day 8: Santa Fe to Albuquerque<\/h4>\n\n\n\n<p class=\"wp-block-paragraph\"><strong>Mileage:<\/strong> ~65 miles<\/p>\n\n\n\n<p class=\"wp-block-paragraph\">Take a shorter day.<\/p>\n\n\n\n<p class=\"wp-block-paragraph\">Highlights:<\/p>\n\n\n\n<ul class=\"wp-block-list\">\n<li>Turquoise Trail scenic route<\/li>\n\n\n\n<li>Old Town Albuquerque<\/li>\n\n\n\n<li>Route 66 neon signs<\/li>\n\n\n\n<li>Indian Pueblo Cultural Center<\/li>\n<\/ul>\n\n\n\n<p class=\"wp-block-paragraph\">Overnight: Albuquerque<\/p>\n\n\n\n<h4 class=\"wp-block-heading\">Day 9: Albuquerque to Gallup<\/h4>\n\n\n\n<p class=\"wp-block-paragraph\"><strong>Mileage:<\/strong> ~140 miles<\/p>\n\n\n\n<p class=\"wp-block-paragraph\">Highlights:<\/p>\n\n\n\n<ul class=\"wp-block-list\">\n<li>Laguna Pueblo<\/li>\n\n\n\n<li>Grants mining history<\/li>\n\n\n\n<li>Continental Divide crossing<\/li>\n\n\n\n<li>Historic El Rancho Hotel in Gallup<\/li>\n<\/ul>\n\n\n\n<p class=\"wp-block-paragraph\">Overnight: Gallup<\/p>\n\n\n\n<h4 class=\"wp-block-heading\">Day 10: Gallup to Holbrook, Arizona<\/h4>\n\n\n\n<p class=\"wp-block-paragraph\"><strong>Mileage:<\/strong> ~95 miles<\/p>\n\n\n\n<p class=\"wp-block-paragraph\">Highlights:<\/p>\n\n\n\n<ul class=\"wp-block-list\">\n<li>Petrified Forest National Park<\/li>\n\n\n\n<li>Painted Desert<\/li>\n\n\n\n<li>Route 66 alignment through the park<\/li>\n\n\n\n<li>Wigwam Motel<\/li>\n<\/ul>\n\n\n\n<p class=\"wp-block-paragraph\">Overnight: Holbrook<\/p>\n\n\n\n<h4 class=\"wp-block-heading\">Day 11: Holbrook to Williams, Arizona<\/h4>\n\n\n\n<p class=\"wp-block-paragraph\"><strong>Mileage:<\/strong> ~190 miles<\/p>\n\n\n\n<p class=\"wp-block-paragraph\">Highlights:<\/p>\n\n\n\n<ul class=\"wp-block-list\">\n<li>Winslow\n<ul class=\"wp-block-list\">\n<li>&#8220;Standin&#8217; on the Corner&#8221; Park<\/li>\n<\/ul>\n<\/li>\n\n\n\n<li>Meteor Crater<\/li>\n\n\n\n<li>Flagstaff&#8217;s preserved Route 66 district<\/li>\n\n\n\n<li>Historic Williams<\/li>\n<\/ul>\n\n\n\n<p class=\"wp-block-paragraph\">Overnight: Williams<\/p>\n\n\n\n<h4 class=\"wp-block-heading\">Day 12: Grand Canyon Excursion<\/h4>\n\n\n\n<p class=\"wp-block-paragraph\"><strong>Mileage:<\/strong> ~120 miles round trip<\/p>\n\n\n\n<p class=\"wp-block-paragraph\">Highlights:<\/p>\n\n\n\n<ul class=\"wp-block-list\">\n<li>Full day at Grand Canyon National Park<\/li>\n\n\n\n<li>Return to Williams<\/li>\n<\/ul>\n\n\n\n<p class=\"wp-block-paragraph\">Overnight: Williams<\/p>\n\n\n\n<h4 class=\"wp-block-heading\">Day 13: Williams to Barstow, California<\/h4>\n\n\n\n<p class=\"wp-block-paragraph\"><strong>Mileage:<\/strong> ~360 miles<\/p>\n\n\n\n<p class=\"wp-block-paragraph\">Highlights:<\/p>\n\n\n\n<ul class=\"wp-block-list\">\n<li>Seligman (birthplace of Route 66 preservation)<\/li>\n\n\n\n<li>Hackberry General Store<\/li>\n\n\n\n<li>Kingman<\/li>\n\n\n\n<li>Oatman wild burros<\/li>\n\n\n\n<li>Mojave Desert crossing<\/li>\n\n\n\n<li>Barstow Route 66 Museum<\/li>\n<\/ul>\n\n\n\n<p class=\"wp-block-paragraph\">Overnight: Barstow<\/p>\n\n\n\n<h4 class=\"wp-block-heading\">Day 14: Barstow to Santa Monica<\/h4>\n\n\n\n<p class=\"wp-block-paragraph\"><strong>Mileage:<\/strong> ~130 miles<\/p>\n\n\n\n<p class=\"wp-block-paragraph\">Highlights:<\/p>\n\n\n\n<ul class=\"wp-block-list\">\n<li>Elmer&#8217;s Bottle Tree Ranch<\/li>\n\n\n\n<li>San Bernardino&#8217;s McDonald&#8217;s Museum site<\/li>\n\n\n\n<li>Pasadena sections of historic Route 66<\/li>\n\n\n\n<li>End at the famous Santa Monica Pier &#8220;End of the Trail&#8221; sign<\/li>\n<\/ul>\n\n\n\n<p class=\"wp-block-paragraph\">Celebrate with sunset on the Pacific Ocean.<\/p>\n\n\n\n<h4 class=\"wp-block-heading\">Don&#8217;t Miss Top 10 Route 66 Stops<\/h4>\n\n\n\n<ol class=\"wp-block-list\">\n<li>Route 66 Begin Sign, Chicago<\/li>\n\n\n\n<li>Chain of Rocks Bridge, Missouri<\/li>\n\n\n\n<li>Blue Whale of Catoosa, Oklahoma<\/li>\n\n\n\n<li>Cadillac Ranch, Texas<\/li>\n\n\n\n<li>MidPoint Caf\u00e9, Adrian, Texas<\/li>\n\n\n\n<li>Santa Fe Historic Plaza<\/li>\n\n\n\n<li>Petrified Forest National Park<\/li>\n\n\n\n<li>Wigwam Motel, Holbrook<\/li>\n\n\n\n<li>Oatman, Arizona<\/li>\n\n\n\n<li>Santa Monica Pier<\/li>\n<\/ol>\n\n\n\n<p class=\"wp-block-paragraph\"><strong>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<p class=\"wp-block-paragraph\">For a true Route 66 enthusiast, I&#8217;d also suggest adding a few extra nights in <strong>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":"<p>If you want to experience as much of the original Route 66 as possible, I&#8217;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&#8217;s most iconic small towns. Day 1: Chicago, Illinois to Springfield, Illinois Mileage: ~200 &hellip; <\/p>\n<p class=\"link-more\"><a href=\"https:\/\/travellogs.co.uk\/wordpress\/?page_id=1677\" class=\"more-link\">Continue reading<span class=\"screen-reader-text\"> &#8220;14 day Route 66 Road Trip: Chicago to Santa Monica&#8221;<\/span><\/a><\/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-1677","page","type-page","status-publish","hentry","entry"],"_links":{"self":[{"href":"https:\/\/travellogs.co.uk\/wordpress\/index.php?rest_route=\/wp\/v2\/pages\/1677","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/travellogs.co.uk\/wordpress\/index.php?rest_route=\/wp\/v2\/pages"}],"about":[{"href":"https:\/\/travellogs.co.uk\/wordpress\/index.php?rest_route=\/wp\/v2\/types\/page"}],"author":[{"embeddable":true,"href":"https:\/\/travellogs.co.uk\/wordpress\/index.php?rest_route=\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/travellogs.co.uk\/wordpress\/index.php?rest_route=%2Fwp%2Fv2%2Fcomments&post=1677"}],"version-history":[{"count":5,"href":"https:\/\/travellogs.co.uk\/wordpress\/index.php?rest_route=\/wp\/v2\/pages\/1677\/revisions"}],"predecessor-version":[{"id":1690,"href":"https:\/\/travellogs.co.uk\/wordpress\/index.php?rest_route=\/wp\/v2\/pages\/1677\/revisions\/1690"}],"wp:attachment":[{"href":"https:\/\/travellogs.co.uk\/wordpress\/index.php?rest_route=%2Fwp%2Fv2%2Fmedia&parent=1677"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}