Chicago to St. Louis in One Day: Historic Route 66

Route 66 begins, officially, on a Chicago street corner: a small brown sign on Adams Street that reads Begin Historic Route 66. From there the Mother Road once ran southwest across Illinois to St. Louis, and a day is enough to taste it. This trip does not try to drive every mile of the original pavement; it stitches the best stops together with the interstate, and holds the old road through Wilmington and Litchfield where it is worth it.

The morning is the drive south on I-55, dipping into Wilmington to roll past the Gemini Giant, a green-suited fiberglass astronaut with a rocket that became one of the best-known roadside figures on the route (it now stands in a Wilmington park; a photo stop is listed as an option). Then Pontiac, a small town that has turned its Route 66 heritage into a museum and a street of murals. The Route 66 Hall of Fame & Museum, run on donations, is the first stop.

Springfield is the middle of the trip and the second stop, with two parts a short drive apart: a Cozy Dog, the fried hot dog on a stick that its makers say they invented, at a diner on old Route 66 (S 6th Street), then a free ticket and a 30-minute guided walk through the only house Abraham Lincoln ever owned, in a neighborhood restored to its 1860s look.

Afternoon brings the run to St. Louis, with a pass through Litchfield where the old road still runs by the Ariston Cafe, and a walk on the Old Chain of Rocks Bridge, the 1929 Mississippi River crossing whose 22-degree bend in the middle made it famous. The finish is the Gateway Arch grounds for a look up at the 630-foot curve. Ted Drewes Frozen Custard, a Route 66 landmark on Chippewa Street, is an optional dessert detour of about 23 extra minutes.

The numbers: 325.7 miles and 5 h 49 min of pure driving across five legs, no tolls, and four stops (Pontiac, Springfield, Chain of Rocks, and the Arch finale) with Springfield split into lunch and Lincoln Home. It is one long day of about 11.5 hours from the Begin sign to the Arch, so the museum, Lincoln Home and Chain of Rocks closing times shape the schedule. Anyone who wants to linger has two suggested overnights, in Springfield and in downtown St. Louis.

Assumptions. This plan assumes a Monday-to-Saturday departure (Cozy Dog is closed Sundays and the Ariston Cafe (an option) is closed Mondays) leaving the Begin sign at 6:45 am and Chicago at 7:00 am; times are typical drive times without live traffic, so add slack for the Chicago morning and St. Louis evening rush hours.

Driving demand: easy. Paved interstate and city streets, no mountains or remote stretches, 325.7 miles and 5 h 49 min of driving in one long day (about 11.5 hours with stops). The demand is length and city traffic, not the road. Fuel in Pontiac or Springfield.

Route. Leg 1 uses I-55 with an old-alignment detour through Wilmington (via waypoint at the Gemini Giant); leg 2 is interstate; leg 3 is city streets on old Route 66; leg 4 is interstate (with the Missouri-side Chain of Rocks Park as the endpoint) with a via-waypoint at Litchfield on Old Route 66; leg 5 is surface streets along the St. Louis riverfront. Each leg's route note records the waypoints used.

Tolls. None: the routed roads (I-55, Lake Shore Drive, Missouri surface streets) are not Illinois Tollway roads, and no leg uses a toll road (as of 2026-10-01). Same on cash/toll-by-plate and on a transponder.

Reservations and tickets. Lincoln Home tour tickets are free but issued in person, same day only. Gateway Arch tram and film need tickets; the Arch grounds are free. Pre-purchase Arch parking through the preferred-parking page.

Best months. April-June and September-October: museum and park hours are longest, weather is mild, and daylight covers Chain of Rocks. Summer is hot; winter has short days (Pontiac hours shorten November to March, and the Chain of Rocks park closes 30 minutes after sunset).