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On the road for a mother‑and‑daughter getaway, travel writer Hannah Stephenson and her daughter Grace drove the opening leg of America’s most storied highway, tracing the original path of Route 66 from Chicago to St Louis. The short trip captures a slice of neon, classic diners and roadside oddities that still define the “Mother Road” a century after its creation.
Why Route 66 endures
Established in 1926, Route 66 was built to connect Midwestern industry with the agricultural Southwest and to boost commerce along a continuous highway. It also became an important corridor during the Great Migration, as African American families moved north in search of work and safety.
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Although the official designation was retired in 1985 in favour of faster interstates, much of the historic route remains driveable. In Illinois, for example, more than 90% of the original 301 miles can still be followed on the old road, complete with period brick sections and preserved signage.
Starting point: Chicago
Chicago remains the eastern gateway. This year the city added a new Route 66 start marker at Navy Pier, echoing a symbolic pier‑to‑pier link with Santa Monica on the Pacific coast, while the original “Begin” sign is still visible downtown at Jackson Boulevard and Michigan Avenue.
Visitors can see the city from high above at the Skydeck in the Willis Tower on the 103rd floor, and first‑time tourists often use the Chicago CityPASS (listed in US dollars) to bundle access to major sights. For a central base, the Fairmont Chicago, Millennium Park is within easy walking distance of the Bean and river cruises; the hotel is offering special Route 66‑themed packages this year.
Food stops along the city’s first miles include historic diners such as Lou Mitchell’s, operating since 1923 and famous for breakfast, and The Berghoff, which dates back to 1898. A colourful mural at Lulu’s has become a popular roadside photo stop, and locals will warn you against asking for ketchup on a classic Chicago hot dog.
Small towns and cinematic detours: Joliet and Pontiac
About an hour from Chicago, Joliet is a draw for film fans. The Joliet Area Historical Museum displays mannequins of Jake and Elwood from The Blues Brothers, and nearby the Old Joliet Prison—built in the 1850s—now operates as a museum. The site once held nearly 2,000 inmates; visitors can see the tiny original cells and learn about the prison’s history since it reopened to the public in 2018.
Pontiac offers a community feel, anchored by the 1875 Livingston County Courthouse. The downtown is a patchwork of restored storefronts, Route 66 murals and parked vintage cars. Museum complexes there include a trove of memorabilia and the Pontiac‑Oakland Museum’s collection of classic automobiles. During summer months, Cruise Night on the third Saturday of each month (through August) brings car enthusiasts into the streets.
Springfield: history and Route 66 memory
Two hundred miles southwest of Chicago, Springfield is where Abraham Lincoln’s legacy is most visible in Illinois. The city also figures in contemporary political history: it was the place Barack Obama launched his 2008 presidential campaign.
The Illinois State Museum recently opened an exhibit titled Miles Of Memories: Stories of Route 66, featuring neon signage, oral histories and other memorabilia documenting life along the highway. For a kitsch‑rich evening, the Route 66 Motorheads Bar & Grill combines museum pieces with a themed menu—items named after car parts sit alongside classic burgers and bar fare.
Reaching St Louis — end of the first leg
Crossing the Mississippi on the Martin Luther King bridge brings travellers into Missouri and marks the end of the Chicago‑to‑St Louis stretch. St Louis offers a variety of attractions: the 630‑foot Gateway Arch, craft breweries and the Missouri Botanical Garden all sit within easy reach.
For Route 66 enthusiasts, the mile‑long Old Chain Of Rocks Bridge is a highlight. Famous for its unusual 22‑degree bend, the bridge is now open only to pedestrians and cyclists and preserves a tangible link to the road’s past.
After days of diners and neon, many travellers choose to unwind. The Four Seasons Hotel St Louis, which recently completed a major spa refurbishment, provides riverside views and fine dining at Ramsay’s Kitchen; summer room rates are quoted in US dollars in the hotel’s information.
Practical information and bookings
For those who prefer organised travel, the UK operator America As You Like It advertises a seven‑night Illinois and Missouri Route 66 itinerary priced at £2,280 per person (based on two sharing). The package includes British Airways flights from Heathrow to Chicago with a return from St Louis, three nights at the Fairmont Chicago, one night in Pontiac, one night in Springfield, two nights at the Four Seasons in St Louis, five days of car hire and a one‑way drop fee.
For planning and further details, official tourism sites include visittheusa.com, choosechicago.com, enjoyillinois.com, explorestlouis.com, visitspringfieldillinois.com and hcdestinations.com.
