# Route 66, part one: Chicago to Oklahoma City

> 4-day road trip of about 1,405 km (873 mi) with 12 stops, from Chicago to Oklahoma City. About 15 h 35 min of driving in total.

Source: https://camping-spirit.com/guides/route66-east/

**At a glance:** 4-day road trip of about 1,405 km (873 mi) with 12 stops, from Chicago to Oklahoma City. About 15 h 35 min of driving in total. From the Begin sign on Adams Street, through cornfields and Ozark caves, to the neon of Oklahoma.

| | |
|---|---|
| Distance | 1,405 km (873 mi) |
| Driving | 15 h 35 min |
| Suggested days | 4 |
| Stops | 12 |
| Route | Chicago → Oklahoma City |
| States | IL, MO, OK |
| Updated | August 2, 2026 |

## Route description

Start in downtown Chicago at the Route 66 Begin sign on Adams Street, mile zero of the old highway, and follow the brown historic-route signs southwest out of the city. Traffic eases beyond Joliet, and at Wilmington the Gemini Giant, a 30-foot fiberglass spaceman holding a rocket, stands beside the road. From there the route crosses flat Illinois farmland, mostly alongside I-55, to the state capital, Springfield.

At St. Louis the Old Chain of Rocks Bridge crosses the Mississippi with a 22-degree bend in the middle; it is open only to walkers and cyclists, so park and walk out onto it. In the city, Ted Drewes on Chippewa Street has served frozen custard since 1941, and a “concrete” is the thing to order. Southwest of St. Louis the land starts to roll into the Ozarks, and Meramec Caverns at Stanton runs guided tours through multi-level limestone caves.

The old road follows I-44 across Missouri to Joplin, clips the corner of Kansas for a few miles and enters Oklahoma. Near Tulsa, the Blue Whale of Catoosa sits in a spring-fed pond beside Route 66, a good place to stretch your legs. West of Tulsa the two-lane alignment runs through small towns roughly parallel to the Turner Turnpike, a toll road you can use if you are short of time.

At Arcadia, the restored 1898 Round Barn and the 66-foot neon soda bottle of Pops 66 Soda Ranch are a short drive apart, and Pops is at its best lit up at dusk. Oklahoma City is less than an hour further on. In towns the historic alignment changes often, so a turn-by-turn Route 66 guide or app saves a lot of backtracking; spring and fall are the most comfortable seasons, and large motorhomes will find parking easier outside central Chicago and St. Louis.

## Stop-by-stop itinerary

1. **Chicago** (IL)
2. **Route 66 Begin Sign** (Chicago, IL): The brown sign on Adams Street marks mile zero of the Mother Road. Grab the photo, then point the car southwest.
3. **Gemini Giant** (Wilmington, IL): A 30-foot fiberglass spaceman holding a rocket, one of the best-loved "muffler men" on the old highway.
4. **Springfield** (IL)
5. **Old Chain of Rocks Bridge** (St. Louis, MO): A mile-long former Route 66 bridge over the Mississippi with a 22-degree bend in the middle. Now open to walkers and cyclists only.
6. **Ted Drewes Frozen Custard** (St. Louis, MO): A walk-up custard stand on Chippewa Street since 1941. Order a "concrete", thick enough to serve upside down.
7. **Meramec Caverns** (Stanton, MO): Guided tours through multi-level limestone caves, advertised on barn roofs up and down the old highway for generations.
8. **Joplin** (MO)
9. **Blue Whale of Catoosa** (Catoosa, OK): A grinning concrete whale built in the early 1970s as an anniversary gift. It sits in a spring-fed pond beside Route 66.
10. **Arcadia Round Barn** (Arcadia, OK): A true round barn from 1898, restored by local volunteers. The loft hosts dances and a small museum.
11. **Pops 66 Soda Ranch** (Arcadia, OK): Look for the 66-foot neon soda bottle. Inside, coolers hold hundreds of soda flavors from around the world.
12. **Oklahoma City** (OK)