You can make Chicago to St. Louis in about 4.5 hours, but the people who love this drive never do it in one straight shot. At around 300 miles on I-55 (old Route 66), it is short enough to start after breakfast and long enough to earn a night somewhere memorable close to the park gates.
Open this route in XCRSNLeaving Chicago
Aim to clear Chicago before the morning rush, or after it, never in it. Fill the tank on the edge of town where prices usually drop, set the playlist, and settle in for the first 136 miles to Bloomington.
The headline stop on this route is Route 66 Hall of Fame in Pontiac. Leave real time for it; it sets the tone for the whole trip.
Bloomington
Bloomington sits about 136 miles in. It makes a good spot to stretch, eat something that is not from a gas station, and swap drivers.
Nearby, Lincoln Home in Springfield is worth the short detour if the day is going well.
Springfield, the last stretch
Springfield sits about 204 miles in. It is the natural place to stop for the night: hotels are plentiful, rates beat the big-city ends of the route, and you wake up with the hardest miles already behind you.
Rolling into St. Louis
The final 97 miles always go faster than you expect. Save a little energy for Gateway Arch; it is a fitting finish.
By the end you will have seen Route 66 Hall of Fame in Pontiac, Lincoln Home in Springfield and Gateway Arch, and you will understand why this corridor is a classic.
When to go and how to pace it
One night is the sweet spot. Springfield, IL is where most people stay, so book ahead on summer weekends.
Check live gas prices along I-55 (old Route 66) before you go; they can swing a lot from one state or county to the next. XCRSN prices every leg for your exact car.
