Why this ride
A one-way ride of 354 km, Chicago Loop to Pontiac - roughly 4 h 51 in the saddle. A steady touring day rather than a sprint.
CURVESCOUT / MOTORCYCLE RIDE
Historic Route 66: Chicago to Pontiac
Plan this ride
- Recorded distance
- 354 km
- Riding-time estimate
- 4 h 51
- Journey
- One way; return travel is separate
Distance and timing basis
Ordered leg totals agree within rounding. Stop distances are approximate sums of rounded legs. Stops, delays, approach and any separate return travel add time. Basis: planning record, not independently verified geometry.
Reading history stays on this device. My road watch requires a separate selection; opening it does not subscribe this ride.
Distances and riding times are planning figures. Check local closures and conditions before you ride.
Waypoint introductions and full write-ups
1. Chicago
Route 66 begins in the middle of the Loop, a few steps from Lake Michigan, on a downtown street where a small brown sign marks the start of the road that once ran to Los Angeles. Chicago was the logical beginning. By 1926, when the highway was commissioned, the city was already the rail and trade hub of the Midwest, and farm families, migrants and travellers poured out of here along the road westward, the one that John Steinbeck later called the Mother Road.
Read the complete Chicago write-up.
Recorded stop-planning note
May refer to an earlier itinerary; verify against your selected route before riding.
Planning note
Chicago is where the day begins. Next is Joliet.
2. Joliet
Joliet is not pretty and does not pretend to be, which is exactly why it makes a good Route 66 stop. It is an industrial city on the Des Plaines River, southwest of Chicago, with limestone quarries, steel mills, railway yards and a long history of making things and moving them. The old highway came through here on its way out of the metropolitan area, and the town still wears the road lightly, with a few vintage signs and diners and a welcome centre that tells you where to look.
Read the complete Joliet write-up.
Recorded stop-planning note
May refer to an earlier itinerary; verify against your selected route before riding.
Planning note
Joliet comes up about 138 km into the recorded legs. Next is Pontiac.
3. Pontiac
Pontiac, Illinois, is a courthouse town of around twelve thousand people on the Vermilion River, and for anyone with a soft spot for Route 66 it is something close to a pilgrimage. The old highway slips through the middle of town on Old Route 66, and the people here have made a point of keeping its memory alive, with museums, murals and tidy brick storefronts that make a pleasant stop in the middle of the flat Illinois farmland.
Read the complete Pontiac write-up.
Recorded stop-planning note
May refer to an earlier itinerary; verify against your selected route before riding.
Planning note
The route ends here after 354 km.
Leg by leg
Chicago to Joliet
Chicago → Joliet is 138 km of getting across. Ride it tidily and keep the enthusiasm for what comes after.
Joliet to Pontiac
Joliet → Pontiac is 216 km of getting across. Ride it tidily and keep the enthusiasm for what comes after.