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The journey begins near Chicago’s iconic Buckingham Fountain, with an early breakfast of salmon Benedict or an apple and cheese omelet at Lou Mitchell’s Restaurant and Bakery.
Stop in at Joliet’s Route 66 Welcome Center to plan your trip. Visits to the grand Rialto Square Theatre reveal its signature Greek, Roman and Byzantine architecture.
Thousands of artifacts and memorabilia stand out at Pontiac’s Route 66 Association Hall of Fame. Pork chop sandwiches and other comfort foods await at the Old Log Cabin, a longtime Pontiac favorite.
Restored 1930s service stations filled with vintage tools remain at Ambler Becker Texaco Gas Station in Dwight and at Odell’s Standard Oil Gas Station.
Atlanta’s J.W. Hawes Grain Elevator offers self-guided tours of the vintage building, and you’ll love the pie at Palms Grill Cafe.
The decor at themed Route 66 Hotel and Conference Center in Springfield consists of miniature cars, gas pumps and motorcycles (from $66).
The collectibles and antiques at Becky’s Barn are worth the turn down a small brick road in Auburn.
The Million Dollar Courthouse proves interesting for its architecture and stories of corruption.
In Collinsville, check out the World’s Largest Catsup Bottle.
Ask to see the scrapbook of Route 66 travelers and sample the fried artichoke hearts and tenderloin at The Ariston Cafe in Litchfield.
In Livingston, a 1940s gymnasium houses The Pink Elephant Antique Mall, where you’ll find bargain booths of vintage clothing, furniture and books.
Thick pork chops and berry cobbler satisfy diners in the relaxed atmosphere of Weezy’s Route 66 Bar and Grill in Hamel.
Add a day
At Livingston County War Museum in Pontiac, stories of wartime and military weaponry pay tribute to soldiers. An often-changing lineup of autos reveals vintage Pontiac station wagons, Oakland cars and Pontiac race cars at Pontiac-Oakland Museum and Resource Center. The town’s 24 outdoor murals showcase the local cultural scene, and three swinging bridges cross the Vermilion River from Chautauqua Park to Play Park.
One big party!
Each fall, hundreds of hot rods and vintage motorcycles pour into Springfield for the Route 66 Mother Road Festival. Live music, vendors and outdoor concerts fuel the fun (September 26–28, 2014). Don’t miss out on the free car show. (800) 545-7300; visit-springfieldillinois.com 
More information: Route 66 (815) 844-4566; il66assoc.org