Fun Photo Spots Along the First Stretch of Route 66 in Illinois

Begin your journey with a day and night in Chicago to see the sights, including the historic starting point of Route 66 at Michigan Avenue and Adams Street. Get an early-morning start for the 60-minute drive to Joliet. For your first stop, head to the Joliet Area Historical Museum and The First Hundred Miles Welcome Center. Pose with statues of fictional musical duo the Blues Brothers and learn more about the city and its attractions.

Shop in downtown Joliet’s unique shops, then grab lunch at locally-owned coffee house Jitters before visiting the Old Joliet Prison. Pick up a tour ticket for a self-guided exploration of the towering limestone edifice, which has housed notorious real-life criminals – and some fictitious ones, including "Joliet" Jake Blues of the Blues Brothers and Michael Scofield from acclaimed television show “Prison Break.”

As you head out of town, grab an ice cream treat at Rich & Creamy, then follow Route 66 to the Route 66 Raceway to watch drivers of the National Hot Rod Association compete in exciting drag races.

Take a short jaunt west off Route 66 to several places in the I&M Canal Heritage Corridor. Towns such as Morris, Marseilles and Ottawa that are clustered along the I&M Canal offer trendy boutiques, antique shops and a range of dining options. Pose next to Starved Rock State Park’s amazing seasonal waterfalls and rocky cliffs in Oglesby. Head to LaSalle, St. Louis, French and Ottawa canyons for the best views in spring or winter, when the waterfalls freeze into icefalls, and check out the dramatic sandstone bluffs. After taking in the sights, head back to Route 66 and resume your drive south.

The stops between Joliet and Pontiac are truly entertaining. The town of Wilmington is home to the Gemini Giant, a 9-meter-tall fiberglass statue hearkening back to the unique advertising along Route 66. Thirsty for a craft beer? Rt. 66 Old School Brewing is a perfect stop to grab a pint.

You can also get some great shots at Braidwood’s Polk-a-Dot Drive In, home to several 2-meter-tall statues, including Elvis Presley, Marilyn Monroe and Betty Boop. Gardner’s Two-Cell Jail is also worth a quick stop; get locked up for a great selfie.

Main Street in downtown Pontiac is adorned with over 25 outdoor murals painted by the internationally known Walldogs. The most-snapped photo is behind the Route 66 Hall of Fame and Museum; the mural is the world’s largest outdoor Route 66 painted shield. Go inside the museum to learn more about top attractions and locations along Route 66 in Illinois. Don’t miss the chance to take a photo of famous artist Bob Waldmire’s van, which was the inspiration for the Fillmore character in the Walt Disney Pictures movie “Cars.”

Around the corner is the Pontiac-Oakland Automobile Museum, which pays homage to the Pontiac and Oakland automobile brands. Don’t miss touring the Museum of Guilding Arts or Livingston County War Museum as well. Great dining stops in Pontiac include Edinger’s Filling Station and the Old Log Cabin. Both locations serve food that is reminiscent of the mom-and-pop diners of the past. Save room for dessert.

Fly in to Chicago’s international airports O’Hare (ORD) or Midway (MDW), where you can rent a car and drive about 60 minutes to get to Joliet. Trains, buses and ride-share services also are available at the airports.