How Many Days for Illinois?
Illinois Route 66 stretches 301 miles from downtown Chicago to the Chain of Rocks Bridge at the Mississippi River. It's the starting line of the Mother Road, packed with iconic stops, quirky roadside attractions, and one of America's greatest cities. Here's how to plan your time.
1The Express Run — 1 Day
If you're in a hurry, you can drive Chicago to the Chain of Rocks Bridge in about 4.5 hours on I-55. Add quick stops at the Route 66 Begin Sign, the Gemini Giant in Wilmington, and the Cozy Dog Drive In in Springfield, and you've got a packed 10-hour day. You'll miss most of what makes Illinois Route 66 special, but you'll hit the iconic photo ops.
2The Sweet Spot — 2–3 Days (Recommended)
Day 1: Chicago — Route 66 Begin Sign at Grant Park, Lou Mitchell's Restaurant for breakfast, Willis Tower Skydeck, deep-dish pizza. Drive to Joliet or Pontiac.
Day 2: Joliet to Springfield — Gemini Giant in Wilmington, Polk-a-Dot Drive In in Braidwood, Route 66 Hall of Fame in Pontiac, Funks Grove, Cozy Dog Drive In in Springfield, Lincoln's Tomb. Stay in Springfield.
Day 3: Springfield to Chain of Rocks Bridge — Lincoln Home National Historic Site, Cahokia Mounds (UNESCO World Heritage Site), Chain of Rocks Bridge walk. Cross into Missouri.
3The Deep Dive — 4–5 Days
This pace lets you explore Chicago properly (2 days minimum for the city alone), then spend 2–3 days on the downstate route. You'll have time for the Pontiac murals walking tour, the Atlanta Library smiley face water tower, Litchfield's Sky View Drive-In, and every quirky roadside stop. Add a detour to Starved Rock State Park for hiking, or spend an evening at one of Springfield's Lincoln-era sites.
4Overnight Recommendations
Night 1: Chicago — wide hotel selection, stay near Grant Park for Route 66 Begin Sign access. Night 2: Pontiac or Bloomington — Pontiac puts you near the murals and Route 66 Hall of Fame. Night 3: Springfield — the Route 66 capital of Illinois, with the most dining options downstate.
lightbulbPro Tips
2–3 days is ideal — one day for Chicago, one for the downstate drive, one for Springfield and the Mississippi crossing.
Don't underestimate Chicago — even a half-day there feels rushed. Budget at least a full day if it's your first visit.
The Pontiac to Springfield stretch has the densest concentration of Route 66 attractions in the state.
If you only have one day, prioritize the Begin Sign, Gemini Giant, Cozy Dog, and Chain of Rocks Bridge.