Illinois’ Route 66: Touring Classic Stops on the USA’s Mother Road

Fly into Chicago O’Hare International Airport (ORD) or Midway International Airport (MDW) to pick up a rental car and begin your journey. But first, reserve a few days to explore Chicago – there’s just so much to do. In the heart of downtown, take a picture under the “Begin Route 66” historical marker on East Adams Street, between Wabash and Michigan Avenues, then cross Michigan Avenue to explore the Art Institute of Chicago – founded in 1879, it is one of the oldest museums in the USA and the second-largest.

The museum is on the perimeter of Grant and Millennium parks, both home to some of Chicago’s most popular attractions. Watch the spectacular water show (typically running early May through mid-October) at Buckingham Fountain, join the throngs of visitors taking selfies at the mirror-like “Cloud Gate” sculpture (often affectionately called the “bean”), and go rock climbing or let the kids play on the massive playground at Maggie Daley Park. Indulge in upscale shopping on the Magnificent Mile (Michigan Avenue north of the DuSable Bridge), and don’t miss a bird’s-eye view of the city from the Skydeck Chicago more than 400 meters above the street. On your way out to the next stop, grab breakfast or lunch at Lou Mitchell’s Restaurant, a legendary Route 66 eatery.

Historic Route 66 jogs along several highways and state roads to reach Joliet (consult a map for various options, as the road was re-routed over the years). You’ll soon notice an imposing – and perhaps familiar – building right in the middle of the city. The Old Joliet Prison, which operated from 1858 to 2002, was featured in the 1980 movie “Blues Brothers” and the hit TV show “Prison Break.” No tours are available, but it’s a can’t-miss photo op. Next, check out memorabilia and interactive exhibits on local history at the Joliet Area Historical Museum and Route 66 Welcome Center. Be sure to pick up a souvenir at the gift shop. With its Greek, Roman, French and Byzantine-inspired interior, the circa-1926 Rialto Square Theatre is a stand-out stop on Route 66. Take a guided tour and marvel at the architecture. Pause for a picture in front of the “Kicks on 66” sign at Route 66 Park before the one-hour drive to your next destination.

Take Highway 53 to stay on Historic Route 66. Continue on to Pontiac (named after an Ottawa Indian chief, not the American car company), a cozy town with several Route 66 landmarks. Edinger’s Filling Station is locally famous for its scratch-made pies and diner-style breakfast and lunch menu. Check out the small collection of classic cars at the Pontiac-Oakland Automobile Museum and take a tour of the Route 66 Association Hall of Fame & Museum. Housed in a century-old firehouse, the museum boasts a fantastic collection of memorabilia an awesome photo exhibit of landmarks along the entirety of Route 66. Take a picture of the huge Route 66 mural outside the museum and look for more than 20 other murals around downtown. American history buffs should stop at the 1875 courthouse to take a picture with a statue of young Abraham Lincoln; the town has nine historical sites on the Illinois “Looking for Lincoln” trail.

Take in the expansive farmland views and stop for a picture with the giant Paul Bunyon statue in Atlanta, Illinois. Your next stop is the capital city of Springfield, known as the Land of Lincoln for its connection to the much-revered 16th President of the United States. Tour the state-of-the-art Abraham Lincoln Presidential Museum, visit the Lincoln Home National Historic Site and see the Old State Capitol. About 20 minutes northwest of town, explore Lincoln's New Salem State Historic Site, a recreated 1830s village where Lincoln first settled after returning to Illinois as an adult. Lincoln, his wife Mary and three of their children are buried in the Lincoln Tomb at the city’s Oak Ridge Cemetery.

If you're visiting Springfield on the last full weekend of September, don’t miss the International Route 66 Mother Road Festival, when the downtown streets are filled with classic cars, live music and delicious food. Try the original hot dog on a stick at the Cozy Dog Drive In, an iconic Route 66 diner. When the sun goes down, park your car at the Route 66 Drive-In movie theater, grab a bucket of popcorn at the concession stand and enjoy a Hollywood hit under the stars. On your way south the next day, take a slight detour near Auburn to drive the 2.25-kilometer, hand-laid brick stretch of old Route 66 on the National Register of Historic Places.

On the final leg of your trip, there are some fantastic roadside stops you simply have to check out. An hour south of Springfield on historic Route 66, you can’t miss the Pink Elephant Antique Mall in Livingston – literally, you can’t miss it. Outside, there’s a giant statue of a man clad in beach attire, a house shaped like a UFO and, of course, a giant pink elephant statue. Stop to browse the dizzying array of antiques and trinkets, and enjoy a sweet treat at the old Twistee Treat ice cream shop that’s shaped like a giant ice cream cone. Continue south and take another short detour to Weezy’s Bar & Grill in Hamel, a classic dive bar (in all the best ways) with walls plastered in Route 66 memorabilia. Your next stop is quaint and family-friendly Edwardsville. The walkable downtown area has a couple of stops to check out: Dewey’s Pizza for some of the best pizza you’ll ever try, and the Wildey Theatre, a concert and movie house that dates back to 1909. In Glen Carbon just south of Edwardsville, stop for a pretty picture of the covered bridge and the Yanda Log Cabin, built by the town’s blacksmith in 1853. As you head to St. Louis International Airport for the flight home, you’ll want to check out the Old Chain of Rocks Bridge. It’s a portion of Historic Route 66 that connected Illinois to Missouri over the Mississippi River.