Chicago to St. Louis

Chicago is where Route 66 begins, and the drive to St. Louis is the first real test of whether this kind of trip suits you. It's roughly 300 miles of small Illinois towns strung southwest along old two-lane pavement that parallels I-55, each one built around a single reason to pull over — a mural, a diner, a fiberglass giant holding a hot dog. None of it is dramatic scenery. All of it is the point.

This guide covers the Illinois stretch of our Route 66 planning guide, from the "Begin Route 66" sign downtown to the Gateway Arch on the Missouri side of the Mississippi. If you're starting from Chicago itself and the full road trip isn't in the cards yet, our weekend trips from Chicago guide covers shorter options closer to home. And if you're timing this for 2026, you're driving it in a fitting year — Route 66 turns 100, the same year the country marks 250 years since independence, a coincidence our America 250 guide covers in more detail.

The drive at a glance

Here's every stop worth knowing about on this leg, in order, with the rough distance from downtown Chicago and the one-line reason to get off the highway.

Suggested drive time & pacing

Point a GPS straight at St. Louis and I-55 gets you there in five to six hours of pure driving. Nobody who cares about Route 66 actually does that. The reason to drive this leg at all is the two-lane frontage roads and business loops that peel off the interstate through each small town, and those add real time — not because the roads are slow, but because you'll keep stopping.

Treat this as a one- or two-day drive rather than a highway sprint. One day works if you leave Chicago by mid-morning and limit yourself to three or four stops — Joliet, Wilmington, Pontiac, and a late lunch in Springfield before pushing on to St. Louis by evening. Two days is the more comfortable version: Chicago to Springfield on day one, with time to actually walk Pontiac's mural-covered blocks and eat a Cozy Dog without rushing, then Springfield to St. Louis on day two with stops in Litchfield and Staunton along the way.

The historic alignment isn't marked consistently once you're south of Pontiac — download an offline map of the Route 66 business loops before you lose cell coverage in the smaller counties.

Best overnight stops

If you're only stopping once, make it Springfield. It sits a little under two-thirds of the way to St. Louis, which breaks the drive into two sane days instead of one long one, and it's the only town on this leg with enough restaurants, gas stations, and lodging to feel like a real overnight rather than a truck-stop pause. It's also worth a half-day on its own — between the Lincoln sites and the Route 66 history downtown, Springfield rewards slowing down more than anywhere else on this stretch.

Litchfield is the fallback if you want to push further south before stopping, or if Springfield lodging is tight on a busy weekend. It's smaller and quieter, with fewer restaurant options, but it sets up an easy final push into St. Louis the next morning.

Attractions

Joliet's contribution is the old Route 66 visitor center — worth a quick stop for maps and context — plus the restored Rialto Square Theatre downtown, a grand historic movie palace worth a look from the sidewalk even if you don't catch a show. From there, Wilmington delivers the first of several giant roadside statues on this stretch: the Gemini Giant, a towering fiberglass spaceman that's stood roadside for generations of Route 66 travelers to photograph. These "Muffler Man" figures — oversized fiberglass statues originally built to advertise auto shops and other roadside businesses — turn up repeatedly on this drive, and Wilmington's is one of the most recognizable.

Pontiac is the most complete stop on the Illinois leg. The Route 66 Hall of Fame & Museum does a thorough job walking through the road's history state by state, and the town has leaned into its Route 66 identity with dozens of murals covering downtown building walls — enough that you could spend an hour just walking the grid and finding them. A little further south, Atlanta, IL keeps the Muffler Man theme going with "Bunyon's," a hot-dog-holding giant standing watch over the town's small downtown.

Springfield is where the trip becomes about more than Route 66. As the Illinois state capital and Abraham Lincoln's hometown, it has a genuine cluster of historical sites: his preserved home, his tomb, and the Old State Capitol, where he served in the state legislature. None of that is Route 66 history specifically, but it's directly on the way and worth the half-day.

South of Springfield, the stops get smaller and quirkier. Staunton's Henry's Rabbit Ranch is the kind of roadside oddity Route 66 specializes in — a low-key, car-culture-themed collection — and it's a quick, easy stop rather than a destination in itself. As you approach St. Louis, the old alignment runs near the historic Chain of Rocks Bridge, a former auto crossing over the Mississippi now used mainly by pedestrians and cyclists, before the drive delivers you into downtown St. Louis under the Gateway Arch — the clean end point for this leg.

Food & photo stops

A few stops on this leg are worth building meals around rather than just driving past. Lou Mitchell's, near Union Station in Chicago, is the traditional way to start the drive — a diner breakfast before you hit the road for real. In Springfield, the Cozy Dog Drive In claims a piece of corn-dog-on-a-stick history and draws a steady stream of Route 66 travelers for exactly that reason; it's touristy, but touristy for a legitimate reason, and it photographs well.

Further south, Litchfield's Ariston Cafe is one of the oldest continuously operating restaurants on the whole route, which makes it worth a stop on food-history grounds alone, and the neighboring Sky View Drive-In — a classic movie screen still in operation — is worth a photo even if your schedule doesn't allow time for a film. Between the murals in Pontiac and the giant roadside statues in Wilmington and Atlanta, this leg keeps a camera busy without ever pulling you far from the car.

Where to stay

For an overnight in Springfield, downtown puts you closest to the Lincoln sites and an easy walk or short drive to the Cozy Dog and other Route 66 stops — expect a rough range of $90–$160 a night for a standard room outside major events, with chain hotels near the interstate exits typically running toward the lower end. If you're finishing the leg in St. Louis instead, staying near the Gateway Arch and downtown puts you within walking distance of the riverfront and the old Chain of Rocks approach, typically in a similar $100–$180 range depending on the night of the week.

Both towns have options well beyond those two areas, and prices swing with events and season, so it's worth comparing a few neighborhoods against each other rather than booking the first result you see — our hotel area comparison tool is built for exactly that. Wherever you book, see the affiliate disclosure page for how we handle booking partners on this site.

Renting a car & driving tips

If you're flying into Chicago to start the drive, both O'Hare and Midway have a full range of rental counters, and picking up downtown near Union Station is an option too if you'd rather start right at the "Begin Route 66" sign without a detour to the airport first. Either way, book ahead for weekend pickups — small-town Illinois isn't a rental hot spot, so Chicago is where you want the car sorted before you leave.

The driving itself is easy — flat, well-paved, low-traffic outside the Chicago metro — but the old Route 66 alignment isn't one continuous road. It shifts between frontage roads, business loops, and short stretches where the interstate is the only option, and signage for the historic route varies by county. A dedicated Route 66 map or app is worth carrying alongside regular GPS, since a phone mapping app will default you to I-55 and skip the small-town alignment entirely unless you route around it on purpose.

Fuel and food stops come frequently enough that range anxiety isn't a real concern, even in an EV, though charging infrastructure in the smaller towns is thinner than gas stations — worth checking ahead if you're not driving a standard gas rental.

Fill up before leaving Springfield if you're pushing straight through to St. Louis late in the day — gas stations get sparser, and hours less predictable, in the small towns south of Litchfield.

What this leg costs

Budget for this leg breaks into three pieces: gas, one night of lodging if you're splitting the drive into two days, and food. Gas for roughly 300 miles runs somewhere around $35–$55 depending on your vehicle and current prices, and museum admissions along the way — Pontiac's Hall of Fame, the Lincoln sites in Springfield — add another $10–$30 per person if you stop at all of them. Add a $90–$180 hotel night if you're overnighting, plus roughly $60–$100 per couple for two days of diner meals and roadside food, and a two-day version of this leg for two people lands somewhere around $250–$450 all in, before any souvenir shopping.

That's a rough starting point, not a quote. Run your actual numbers — your vehicle's real mileage, how many nights you're adding — through our road trip cost calculator, and if this leg is part of a longer Route 66 run, our trip budget calculator helps you see how it fits into the bigger picture.

Packing checklist

• Offline maps or a dedicated Route 66 app, since phone GPS defaults to the interstate
• Cash for small-town diners and roadside stops that don't take cards
• A camera or a phone with storage to spare — this leg is photo-heavy
• Snacks and water for the stretches between towns, even though none of them run long
• A phone charger and mount, since you'll be navigating on and off the old alignment all day
• Comfortable shoes for walking Pontiac's mural-covered blocks and Springfield's historic downtown
• A light jacket for spring or fall mornings, when this stretch of Illinois can run cool before the afternoon warms up

Continue the drive

This is the first leg of a longer series — the Route 66 overview lays out a mile-by-mile sense of the full route from Chicago to Los Angeles. Once you've crossed into Missouri and worked further down the road, we've also mapped the Oklahoma City to Amarillo leg and, much further on, the Flagstaff to Santa Monica leg that finishes the drive at the Pacific. For trip ideas beyond Route 66, browse the full destinations index.