Route 66 — Chicago to Santa Monica
The Mother Road. ~3,940 km / ~40 hours of pure driving across eight states, typically driven over ~2 weeks. Diners, drive-ins and dust storms. Original alignments and quirky neon survive in pockets — Cadillac Ranch, the Painted Desert, the Santa Monica Pier.
The Route 66 — Chicago to Santa Monica is a 3940 km highway in 8 States, USA. It runs from Chicago, IL to Santa Monica, CA in about 40 hours of driving. Highlights include Springfield, IL, St. Louis Gateway Arch and Cadillac Ranch. Best driven April – October; rated moderate difficulty.
- Road length
- 3940 km
- Duration
- 2 days
- Vehicle
- Car
- Difficulty
- Moderate
- Best season
- April – October
- Likes
- 22,300
Road length is the scenic route itself — your actual door-to-door driving distance depends on where you start and which stops you take.
Best time to drive
April – October
Expect more visitors in July–August peak season; shoulder months (May–June, September) are usually quieter and often offer better light.
High mountain passes on this route can close in winter due to snow. Always check local road status and seasonal closures before setting off.
General guidance only — always confirm local road and weather conditions before departure.
How many days for Route 66 — Chicago to Santa Monica?
Plan around 8 days for this route.
At ~5 hours of driving a day, you'll want 7 overnight stops along the way. The route has 5 recommended stops to help you break it up.
Estimate based on total driving time — actual pace depends on stops, traffic, and breaks.
The route at a glance
Stops along the way
- ●
- 01Open in MapsSpringfield, IL
Lincoln country and original 66 diners.
- 02Open in MapsSt. Louis Gateway Arch
First major landmark.
- 03Open in MapsCadillac Ranch
Spray-paint half-buried Caddies.
- 04Open in MapsGrand Canyon detour
Skip it and you'll regret it.
- 05Open in MapsSanta Monica Pier
The official western terminus sign.
- ◆
Travel tips
- ★Plan ~2 weeks — the 40-hour figure is pure driving time, not trip length.
- ★Use the EZ66 guidebook for original alignments.
- ★Many stretches lack fuel — top up often.
Music for the road
AI-curated mood for this route — open in your favorite player.
Community comments
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Frequently asked
How long does it take to drive the Route 66 — Chicago to Santa Monica?
The Route 66 — Chicago to Santa Monica takes about 40 hours of driving non-stop to cover its 3940 km. Actual trip length depends on how often you stop at viewpoints and towns along the way.
How long is the Route 66 — Chicago to Santa Monica?
The Route 66 — Chicago to Santa Monica is 3940 km long, running from Chicago, IL to Santa Monica, CA.
When is the best time to drive the Route 66 — Chicago to Santa Monica?
Best driven April – October. Expect more visitors in July–August peak season; shoulder months (May–June, September) are usually quieter and often offer better light. High mountain passes on this route can close in winter due to snow. Always check local road status and seasonal closures before setting off.
Is the Route 66 — Chicago to Santa Monica hard to drive?
The Route 66 — Chicago to Santa Monica is rated moderate difficulty. It is classified as a highway.
What are the main stops on the Route 66 — Chicago to Santa Monica?
The route runs from Chicago, IL to Santa Monica, CA, with key stops including Springfield, IL, St. Louis Gateway Arch, Cadillac Ranch, Grand Canyon detour.
Where is the Route 66 — Chicago to Santa Monica?
The Route 66 — Chicago to Santa Monica is located in 8 States, USA. It runs between Chicago, IL and Santa Monica, CA.