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Illinois: The ultimate introduction to Route 66

The Mother Road in a nutshell

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1 May 2019 by Simon Langley

At over 2,200 miles in length, Route 66 can be a daunting proposition, taking up to 18 days to complete properly. That’s a lot of driving, and why many choose to enjoy a sample of it. And, there’s no better place to start than at the beginning of it all – Illinois. In fact, it features the most amount of Route 66 national historic sites of any state, alongside everything from oh-so-kitschy 50s diners and classic car museums to city greats and giant Native American burial grounds. With a map below, here’s our guide.


  1. Chicago
  2. Pontiac
  3. Springfield
  4. Collinsville
  5. Alton and Grafton
  6. Litchfield

Read our full Route 66 itinerary


For many, Chicago has a chip on its shoulder. America’s third-largest city has long been compared to the likes of New York and Los Angeles, its skyscrapers measured, its restaurants graded and exhibitions ranked. In all categories, it comes out fighting. Having been almost entirely rebuilt after the Great Fire of 1871, a cruise along the river is an architectural education, from Art-Deco skyscrapers and neoclassical icons to the erstwhile tallest building – the Willis Tower. And, when you’ve finished marvelling at the world-class Shedd Aquarium and Field Museum of Natural History, there’s a fine-dining scene that’s made Chicago Condé Nast Traveler’s “best restaurant city in America”.

Chicago might have a chip on its shoulder, but it’s a Michelin-starred chip and a shoulder that towers 100 storeys above Lake Michigan. But, the city has plenty of charm all of its own. Don’t miss out on a deep-dish pizza at Giordano's and a Chicago hot dog at Portillo’s before heading to Navy Pier for spectacular views across the skyline, either from a sunset dinner cruise or the Centennial Wheel. Then, end the night in a blues bar, with the genre’s infectious rhythms having migrated upstream along the Mississippi, picking up a certain foot-tapping electric twang.

That’s perhaps what makes the city so appealing. Whether it’s a walking bass line or an architectural riff, Chicago has a knack for taking something and making it its own, often transforming it into something truly world leading. The pizza really is that delicious.

Find out about our Chicago and the Great Lakes itinerary

Deep dish pizza at Giordano's restaurant
Chicago deep dish pizza at Giordano's


Setting off along Route 66 from Chicago, make the Old Joliet Prison your first stop. Built in the 1850s, its limestone, castle-like fortifications have starred in Prison Break and housed the infamous Blue’s Brothers. The 30-foot-tall Gemini Giant spaceman will then introduce you to the Mother Road at its kitsch best before you roll into Pontiac. Home to the Illinois Route 66 Hall of Fame Museum and Pontiac-Oakland Museum, you’ll be treated to literally thousands of artefacts and memorabilia from the road, including the largest shield mural, the ultimate hippy bus and a fantastic array of gleaming classic cars.

Route 66 mural
Route 66 mural, Pontiac


With Abraham Lincoln having practiced law here for 24 years, Springfield offers the chance to learn about the president that abolished slavery and preserved the United States as we know it. The multimedia museum comes with holographic effects, his grand tomb is a monument to sobering grandeur and Lincoln’s original house has been immaculately restored to its 1860 origins, both inside and out.

There’s also the small matter of the state capitol buildings both old and new – respectively lessons in Greek-Revival severity and Neo-Renaissance excess. However, it’s perhaps the Dana Thomas House that lingers longest in the memory. Built at the turn of the 20th century, it represents a coming of age in American architecture, with Frank Lloyd Wright moving away from European influence to usher in a new homegrown school. It’s the chance to see the very genesis of the Art Deco and Modernist movements. Of course, there’s also plenty of Route 66 charm, including an original hand-laid stretch of brick road and Motorheads – part lovable dive bar, part vintage automotive museum.

Glass roof of the Illinois State Capitol
The Illinois State Capitol


On your way through the prairies to Collinsville, you’ll be treated to a trio of Route 66 gems. There’s one of the last original soda fountains in Girard, the world’s largest Catsup ketchup bottle on Route 159, and the Pink Elephant Antique Mall near Livingston. It’s home to everything from a retro diner to countless Americana memorabilia and, yes, a giant pink elephant statue.

Then, rolling into Collinsville, there’s something of the unique. UNESCO-listed Cahokia Mounds is the largest pre-Columbian settlement north of Mexico, and comprised 1,600 hectares of hamlets and villages in its 11th-century heyday. Many of its fortified mounds survive to this day, including what is the largest prehistoric earthwork in the Americas. Be sure to round things off with a craft beer or gin-and-tonic at the award-winning Old Herald Brewery and Distillery.

Exterior of Doc's Soda Fountain
Doc's Soda Fountain, Girard

Alton and Grafton

Alton is small-town America at its best, complete with foot-tapping dive bars and redbrick tea rooms that serve up simply the finest sweet pies. You can even meet its favourite son, with a nine-foot statue of Robert Wadlow – the world’s tallest man. Then, just outside of town on the way to Grafton, there’s a giant Indian painting of a legendary dragon-bird, along with a fantastic winery at Aerie’s Resort. Its deck offers sweeping views over the confluence of the Mississippi and Illinois rivers. Don’t also miss out on spotting that great American icon, with bald eagles common around the National Great Rivers Museum and the Pere Marquette State Park.

The Piasa Bird
The Piasa Bird mural, outside Alton


As you turn back towards Chicago, Litchfield makes the perfect final stop. Its museum is superb, with a whole host of Route 66 memorabilia housed in a charming retro building. Then, finish up with brunch at Jubelt’s Bakery and Restaurant. With a history spanning over 90 years, you can expect everything from oh-so-fluffy pancakes and cinnamon French toast to ribeye sandwiches and the ultimate in country hash browns.

While Litchfield is a fitting end to your trip, remember that you can choose to see as much or as little of Route 66 as you want. And, if you’re flying in and out of Chicago, you can create your own perfect loop. To start organising your tailor-made trip, get in contact with one of our experts today: 

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