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Adam Alexander Photography

Route 66 and beyond

Whether you want to spend just a few hours exploring while you’re on a city break in Chicago or you have time for an all-out adventure, experiencing the Mother Road is a must

By Time Out in association with Illinois Tourist Board

Driving the Route

As the song goes, ‘It winds from Chicago to LA…’ However, you don’t have to do the whole 2448 miles to savour the Route 66 spirit. Book on a coach tour or, ideally, hire a car for a day or two and follow the 300 miles of Route 66 that spans Illinois. It starts downtown, on E Jackson Blvd, and takes you past iconic kitsch sights, famous diners, drive-in theaters and nostalgic Route 66 attractions on the way to the Old Chain of Rocks Bridge, just as it crosses the Mississippi.

Route 66 Association Hall of Fame & Museum

Free to visit and crammed with paraphernalia and memorabilia related in all kinds of ways to the Mother Road, this museum in Pontiac (a couple of hours’ drive from Chicago) is well worth dropping in on when you’re passing through. Hear stories of Route 66 and get a sense of its magic from the homegrown artwork and treasures collected by its devotees.


What to hire

You don’t need to hire an off-roader, a regular car will do. At the height of summer you might find a convertible a little too hot to handle, but as long as you’re armed with a hat and some sun block, going open-top definitely enhances the experience if it takes your fancy. Want to go further? Consider booking a one-way hire so you can fly back to Chicago.

What to see

On a long day’s drive (or an overnight adventure) you can get to Springfield, steeped in the history of President Abraham Lincoln, who made it his hometown. There are several sites to visit, including Abraham Lincoln Presidential Museum, Lincoln Home National Historic Site and Lincoln Tomb. Or just take to the road and explore. Route 66 seems to bring out the best and most quirky in Americana – swing by Doc’s Soda Fountain in Girard and Henry’s Rabbit Ranch in Staunton (it overflows with curious Route 66 ephemera). On your drive, keep a look out for a nine metre astronaut holding a rocket ship in Wilmington, a massive statue of the legendary lumberjack Paul Bunyon wielding a hot dog in Atlanta and the world’s largest  Catsup bottle – in Collinsville. Yes, really!


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