Route 66 Illinois – Map, Attractions & Best Time to Drive
There’s something magical about starting your Route 66 adventure where it all began; right here in Illinois. For 301 miles, from the bustling streets of Chicago to the banks of the Mississippi River, this legendary highway takes you past neon-lit diners, nostalgic roadside stops, and wide-open Midwestern landscapes.
Whether you’re here for a weekend getaway or the first leg of the full Chicago-to-Los Angeles journey, Illinois offers a Route 66 experience that blends history, charm, and a dash of Americana.
Best Time to Drive Route 66 in Illinois
While you can drive Route 66 in Illinois any time of year, the experience changes with the seasons:
- Spring (April–June) – Wildflowers bloom along the roadside, small towns shake off winter, and the weather is comfortably mild.
- Summer (July–August) – It’s festival season, with lively events in many Route 66 towns, but expect warmer days and more travelers.
- Fall (September–October) – The road is framed by fiery foliage, crisp air, and golden sunsets — perfect for photographers.
- Winter (November–March) – Quiet roads and a serene landscape, but be prepared for cold snaps and icy conditions.
💡 Tip: Before you go, check our live weather feature to see conditions along the route. It’s the easiest way to avoid storms and make the most of sunny driving days.
Route 66 Illinois Attractions
Every curve of this road tells a story. Here are a few you won’t want to miss:
- Route 66 Begin Sign – Chicago
Stand at the official starting point and snap that all-important photo. - Joliet Route 66 Diner
Step inside a retro time capsule for a classic American breakfast or slice of pie. - Pontiac Route 66 Museum
Explore vintage cars, murals, and Route 66 memorabilia in a charming small-town setting. - Funk’s Grove Maple Sirup
A sweet pit stop steeped in tradition — and spelled “sirup” the old-fashioned way. - Cozy Dog Drive In – Springfield
Taste history at the birthplace of the corn dog, still family-run today. - Chain of Rocks Bridge
End your Illinois leg with a stroll over this mile-long bridge crossing the Mississippi.
3-Day Route 66 Illinois Itinerary
Day 1: Chicago → Pontiac
- Begin at the Route 66 start sign in downtown Chicago.
- Stop in Joliet and Wilmington for photo ops and coffee breaks.
Day 2: Pontiac → Springfield
- Spend the morning in Pontiac’s museum and mural district.
- Visit Funk’s Grove for maple sirup, then arrive in Springfield for an evening downtown.
Day 3: Springfield → East St. Louis
- Grab lunch at Cozy Dog Drive In.
- End with sunset views from the Chain of Rocks Bridge before crossing into Missouri.
Planning Tips
- Fuel & Facilities: Gas stations are frequent in cities and towns, but rural stretches can be sparse. Plan accordingly.
- Timing: Early departures give you more daylight for sightseeing.
- Events: Look for Route 66 festivals, car shows, and seasonal markets along the way.
Route 66 Illinois Weather
Illinois weather can be as unpredictable as the road itself. In spring and fall, a sunny morning can turn into a quick-moving storm by afternoon.
Our Forecast Slider tool lets you preview conditions along your exact route. From Chicago’s skyline to the rolling farmland. So you can stay ahead of any weather surprises.
FAQs
How long does it take to drive Route 66 in Illinois?
About 6–8 hours without stops. But with all the attractions, you’ll want to stretch it over 2–3 days.
When is the best time to drive Route 66 Illinois?
Late spring and early fall offer the best mix of scenery, weather, and comfortable driving conditions.
Plan Your Route 66 Illinois Trip
Bring your Route 66 Illinois journey to life with our app. Complete with live weather updates, route planning, and must-see stop recommendations.
Download the app now.
