Route 66 in 14 Days: Chicago to Santa Monica by Car

Chicago to the Pacific in fourteen days, 2,450 miles across eight states, driven west so the sun is behind you and the road ends at the ocean. Start with the thing every other Route 66 plan glosses over: there is no Route 66. It was decommissioned on 27 June 1985 and no longer exists as a signed US highway. What survives is a patchwork of alignments — some original concrete you can still drive, some absorbed under I-55, I-44 and I-40, some gone entirely — so every driving day below names its sub-legs and says plainly which parts are the real road and which are interstate. The honest summary: Illinois, Kansas, Oklahoma and the Seligman–Topock arc in Arizona are largely drivable as the original thing; the Texas panhandle is mostly I-40 frontage road; and between Rolla and Lebanon, Holbrook and Flagstaff, and Barstow and San Bernardino you are on the interstate and this plan says so rather than pretending. On the Santa Fe question this build takes the pre-1937 alignment. Route 66 ran Santa Rosa–Las Vegas–Santa Fe–Albuquerque from 1926 to 1937 before the realignment straightened it through Albuquerque, and the older loop is the better choice here for one non-obvious reason: it is not a detour off Route 66, it is Route 66, and it still delivers you into Albuquerque's Central Avenue neon, so you get both cities on genuine alignment for about 150 extra miles and two extra hours spread across days 9–11. Budget about $1,825 per person excluding rooms, and the single biggest line is the car: roughly $780 each for two people sharing a 14-day mid-size hire, of which $350 is the one-way drop fee for leaving a Chicago car in Los Angeles — that fee is not optional on this route, it is quoted at booking, and it is in the day-1 stop cost rather than hidden in a footnote. Add roughly $780 per person for 13 nights of mid-range motels. 2026 is Route 66's centennial year, which means restored sites, more events and noticeably more traffic at the famous stops. The road ends at the Santa Monica Pier, which is exactly where the catalog's `los-angeles-4-days-first-timer` itinerary spends its day 4 — day 14 hands over to it deliberately, so the two files clone into one continuous trip.