Best Road Trip Routes in Illinois

Illinois road trips range from the Route 66 heritage corridor to the Shawnee wine and canyon country to the Lincoln presidential sites.

Route 66 (Chicago to St. Louis)
Illinois contains the original starting stretch of Route 66 — from Chicago's Adams Street southwest through Joliet, Pontiac (the Route 66 Hall of Fame Museum), Bloomington, Springfield (Lincoln sites, the Cozy Dog Drive In — credited with inventing the corn dog), and into St. Louis via the Chain of Rocks Bridge. The 300-mile Illinois stretch is the most culturally rich and well-preserved of any state on Route 66. Allow 2–3 days.

Abraham Lincoln Presidential Trail
From Chicago to Springfield and Lincoln's New Salem — the Lincoln Presidential Library and Museum, the Old State Capitol, Lincoln's Home National Historic Site, and New Salem State Historic Site (the reconstructed 1830s village where Lincoln came of age) are connected by the Illinois presidential trail route. The Lincoln Memorial Garden on Lake Springfield adds natural beauty.

Shawnee Hills Wine Trail and Scenic Byway
In southern Illinois — Alto Pass, Alto Vineyards, Owl Creek Vineyard, and a dozen other wineries in the Shawnee Hills AVA alongside the Garden of the Gods and Giant City State Park. The Shawnee Hills Scenic Byway loops through the hills. Best in fall for foliage and harvest season. The southern tip around Cairo (confluence of Ohio and Mississippi) adds Mississippi River history.

Galena and the Driftless Area
From Chicago northwest on US-20 to Galena — the rolling Driftless landscape, the preserved 1850s lead mining town of Galena, Grant's home, and the Apple River Fort State Historic Site. Galena's Main Street restaurant and inn scene is excellent for a 2-day trip.