The first time I drove Route 66, I was trying to do the whole thing — Chicago to Santa Monica — in eight days. That’s not a road trip, that’s a commute with better scenery. What I didn’t understand until I’d done the full stretch is that the Midwest section, Illinois into Missouri, is actually the most drivable part of the route. The roads are mostly intact, the towns are actual towns rather than ghost infrastructure, and you can do Chicago to St. Louis in two full days and feel like you’ve done something real.
Here’s how to drive it properly.
What Is the Illinois Stretch of Route 66 Actually Like?
The Illinois Route 66 corridor runs roughly 300 miles from Chicago to the Missouri state line near East St. Louis. Unlike the New Mexico or Texas sections where Route 66 has been bypassed and much of the original roadway has crumbled, the Illinois stretch is mostly intact and mostly signed. The Historic Route 66 markers (brown signs with the iconic shield) appear at most turns where the old alignment diverges from modern roads.
The character of the drive changes by section. From Chicago south through the suburbs, you’re moving through standard Midwestern development — strip malls, gas stations, the visual noise of any American edge city. Once you clear Joliet, the landscape opens into Illinois farmland and the driving settles into something actually pleasant: two-lane roads through corn and soybean fields, small cities spaced an hour apart, and a sense that the highway is talking to you about what this part of the country used to be.
Where Do You Start in Chicago?
The official start of Route 66 is at the corner of Michigan Avenue and Adams Street in the Loop — a commemorative sign marks the spot. If you want the spirit of the thing rather than the literal start, I’d begin at the Chicago lakefront (Lake Shore Drive, Grant Park) and work your way through the city before picking up the actual alignment heading south.
Allow most of a morning for leaving Chicago properly. Stop at the Lou Mitchell’s diner on W. Jackson Blvd — it opened in 1923 and has been feeding Route 66 travelers since the highway existed. The hash browns and coffee are exactly what they should be.
What Are the Actual Stops Worth Making?
Joliet (45 miles from Chicago): The Rialto Theatre is a restored 1926 movie palace — opulent Italian Baroque interior, one of the great American theaters. The city also has Route 66 murals and a solid diner scene around the historic commercial district.
Pontiac (100 miles from Chicago): The Illinois Route 66 Hall of Fame and Museum is here, and it’s better than you’d expect — well-curated artifacts and photographs documenting the highway’s history from the 1920s through the postwar car culture years. Free admission. The old town is genuinely intact and worth an hour.
Bloomington-Normal (135 miles from Chicago): The Cruisin’ with Lincoln on 66 Visitor Center is a good resource for the rest of the drive. The twin cities of Bloomington and Normal have decent overnight options if you’re breaking the drive into two days.
Atlanta, Illinois (160 miles from Chicago): A 19-foot fiberglass Paul Bunyan statue holding a hot dog instead of an axe. Route 66 has a specific and earnest relationship with giant roadside folk art, and this is a good early representative of the genre. The adjacent Palms Grill Café has been restored and serves pie worth stopping for.
Springfield (200 miles from Chicago): The state capital, and the single most substantive stop on the Illinois stretch. Abraham Lincoln’s Home National Historic Site (free, National Park Service-operated) is a genuinely moving visit to the only home Lincoln ever owned. The Abraham Lincoln Presidential Library and Museum is the best presidential museum I’ve been to — sophisticated design, serious scholarship, and exhibits that don’t condescend. Allow a half-day minimum.
For dinner in Springfield, the Cozy Dog Drive In is the Route 66 institution — allegedly the birthplace of the corn dog on a stick (the family calls it a “cozy dog”). The Original Route 66 Motor Inn has the period aesthetic if you want to sleep in something thematically appropriate.
Litchfield (240 miles from Chicago): The Ariston Café has been operating since 1924 — Art Deco interior, period stools at the counter, burgers and pie. Open for lunch and dinner. It’s one of the genuine surviving Route 66 restaurants rather than a restoration.
How Do You Cross Into Missouri and St. Louis?
From Litchfield south, the route moves through Staunton (the Henry’s Ra-Lin café is a local lunch institution) and Mitchell before crossing the Mississippi River into St. Louis.
The crossing itself is part of the experience. The Chain of Rocks Bridge — the original Route 66 crossing of the Mississippi — is now a pedestrian and bicycle bridge (closed to vehicles) and you can walk across it for free. The view upriver to the Arch and downtown St. Louis is excellent. The bridge has a mid-river bend — the unusual angle was required to align the span with a water intake structure below.
St. Louis is where the Midwest Route 66 stretch delivers its biggest payoff. The Gateway Arch National Park is the obvious landmark — take the tram ride to the top. Less expected: the City Museum, which is one of the strangest and most genuinely fun places in the Midwest, an enormous industrial building converted into a surrealist playground of slides, tunnels, and salvaged architecture. It’s legitimately hard to describe. Go.
What’s the Best Pace for This Drive?
Two days for the Chicago-to-St. Louis stretch is comfortable — one night in Springfield makes a natural midpoint. Three days if you want to linger at Lincoln sites, take detours into small towns, or visit the Illinois Route 66 Museum in earnest.
If you’re doing the full Route 66 to California, Illinois and Missouri are the easy part. The real logistical complexity starts in Oklahoma and Texas, where long empty stretches require more planning around fuel and lodging. The Midwest section you can wing.
One specific advice: drive south-to-north (St. Louis to Chicago) if you have a preference. The Arch as a starting point is a better visual launch than Michigan Avenue, and you finish with the Chicago lakefront, which is one of the genuinely great urban arrivals in the US.
What Should You Know About Logistics?
Gas is plentiful on this stretch — it’s Illinois, not Arizona. The towns are close enough together that you’re never more than 30 minutes from fuel or food.
Lodging is honest-budget to mid-range throughout. Springfield has the widest selection. Pontiac and Litchfield have period motels that are clean and inexpensive if you want the full Route 66 experience. St. Louis has full hotel infrastructure.
The Illinois Department of Commerce publishes a detailed Route 66 driving guide with the specific alignments (the historic routing deviates from US-66/I-55 at multiple points). It’s available at Illinois state welcome centers and worth picking up before you start.
Cell coverage is solid throughout Illinois and in St. Louis. The rural Missouri sections south of St. Louis (if you’re continuing) have more gaps.
Is This Route Worth It If You’re Not a Highway Nostalgia Person?
Yes, with one condition: you have to be willing to drive 60 mph on two-lane roads through flat farmland and find something interesting in it. If you need dramatic scenery every 20 minutes, the New Mexico section will suit you better.
What Illinois Route 66 offers is horizontal America at its most honest: the scale of the agricultural Midwest, towns that built themselves around the highway and then watched the interstate bypass them, and a specific kind of American ingenuity in figuring out what to do with what’s left. The pie at the Ariston Café is not ironic. The Paul Bunyan hot dog is not a comment on anything. They are exactly what they appear to be, and that’s the point.
For more Midwest road trip ideas, see our Great Lakes Road Trip guide or plan a summer weekend on Lake Michigan. Also check our Chicago destination guide and St. Louis destination guide.
Use the AI Trip Planner to map your overnight stops and timing for the full Illinois stretch.