Illinois holds a unique place in Route 66 historyâit's where the legendary highway began. On April 30, 1926, the federal highway system officially designated U.S. Route 66, and the very first shield marking the road was placed in Springfield, Illinois. For the next 60 years, Route 66 carried millions of travelers from Chicago to Los Angeles, creating an iconic American roadway culture of diners, motels, gas stations, and roadside attractions. Though the interstate system bypassed most of the original route by 1977, Illinois has preserved more of its Route 66 heritage than perhaps any other state.
This guide traces the 301-mile journey of Route 66 through Illinois, from its eastern terminus at Grant Park in Chicago to the Chain of Rocks Bridge crossing into Missouri. Along the way, you'll discover which classic diners still serve travelers, which vintage motels welcome guests, and which roadside giants still stand sentinel over America's Main Street.
The Birth of Route 66
The story of Route 66 begins not on the road, but in Springfield, Illinois. Cyrus Avery, known as the "Father of Route 66," worked with Illinois businessman John Woodruff and the Bureau of Public Roads to create a continuous paved highway connecting Chicago and Los Angeles. When the federal highway system was formalized in 1926, Illinois Route 4 became the eastern portion of U.S. Route 66.
The highway's impact was immediate and transformative. Small towns along the routeâplaces like Atlanta, Dwight, and Pontiacâsuddenly found themselves on America's most traveled road. Gas stations, tourist cabins, restaurants, and attractions sprang up to serve the constant flow of travelers. During the Dust Bowl era, Route 66 became the "Mother Road" for families fleeing drought-stricken farmland, seeking opportunity in California. John Steinbeck immortalized this migration in The Grapes of Wrath, cementing Route 66 in American consciousness.
After World War II, Route 66 entered its golden age. Postwar prosperity, suburban growth, and America's love affair with the automobile turned Route 66 into the nation's premier vacation route. Families packed station wagons and headed west, stopping at themed restaurants, motor courts with neon signs, and roadside curiosities advertised on painted billboards. This era created the nostalgic Americana that Route 66 represents todayâa time when the journey itself was the destination.
Chicago: The Eastern Terminus
Lou Mitchell's Restaurant (1923)
Location: 565 W Jackson Blvd, Chicago, IL 60661
Status: â
Still operating
Since 1923, Lou Mitchell's has served as the unofficial starting point for Route 66 travelers departing Chicago. Located just blocks from the original eastern terminus at Jackson Boulevard and Michigan Avenue (now Grant Park), Lou Mitchell's became a Route 66 institution by treating customers like family. The restaurant's traditionsâfree Milk Duds for women, donut holes for everyone while waiting, and enormous portions of breakfast served all dayâmade it a beloved first stop on westward journeys.
The restaurant's longevity reflects both quality and savvy ownership. Lou Mitchell bought the restaurant in 1949 and ran it for decades, maintaining the same menu, the same orange-roofed booths, and the same friendly service. Today, under third-generation ownership, Lou Mitchell's still packs travelers, locals, and Route 66 enthusiasts into its iconic dining room. Arrive early on weekendsâthe line extends down the block, just as it has for 75 years.
Route 66 "Begin" Sign (Grant Park)
Location: Adams Street & Michigan Avenue, Chicago, IL 60604
Status: â
Accessible landmark
The official starting point of Route 66 has shifted over the years due to route realignments, but today the "Begin Route 66" sign stands at the corner of Adams Street and Michigan Avenue, overlooking Grant Park and Lake Michigan. This brown highway sign, installed by the city, marks where modern Route 66 enthusiasts ceremonially start their journeys westward.
The original 1926 route actually began at Jackson Boulevard and Michigan Avenue (now within Grant Park), running west on Jackson to Ogden Avenue. Later alignments shifted the start to Adams Street or Jackson Street, then to Lake Shore Drive. Regardless of the technical routing, Adams and Michigan has become the accepted "Mile 0" for modern travelers, with the sign serving as a popular photo opportunity.
Joliet: The City of Steel and Stone
Joliet Area Historical Museum
Location: 204 N Ottawa St, Joliet, IL 60432
Status: â
Open to visitors
Joliet's Route 66 history is deeply intertwined with its industrial heritage. As a major steel and limestone center, Joliet thrived during Route 66's heyday, with the highway bringing both workers and travelers through the city. The Joliet Area Historical Museum preserves this history, including exhibits on Route 66's impact on local commerce and tourism. The museum occupies a beautiful limestone buildingâfitting for a city built on quarrying.
Rialto Square Theatre (1926)
Location: 102 N Chicago St, Joliet, IL 60432
Status: â
Still operating as venue
Opening the same year Route 66 was designated, the Rialto Square Theatre represents the opulence of the Roaring Twenties. This "Jewel of Joliet" features a stunning rotunda with a 60-foot ceiling adorned with Greek goddesses, crystal chandeliers, and marble staircases. As Route 66 brought travelers through Joliet, the Rialto served as a cultural beaconâa reminder that even highway towns aspired to sophistication. Today, the fully restored theater hosts concerts, plays, and comedy shows.
Rich & Creamy Ice Cream (Historic Location)
Location: 701 N Broadway St, Joliet, IL 60435 (closed)
Status: â Building remains but business closed
For decades, Rich & Creamy was a Joliet institution where Route 66 travelers stopped for soft-serve cones. The distinctive sign and vintage architecture made it a photo favorite. Though the business has closed, the building still stands as a reminder of Route 66's roadside food culture.
Wilmington: Home of the Gemini Giant
Gemini Giant (1965)
Location: 810 E Baltimore St, Wilmington, IL 60481
Status: â
Still standing (Launching Pad Drive-In closed)
Standing 28 feet tall with a rocket ship in his arms, the Gemini Giant is Illinois' most photographed Route 66 landmark. Built in 1965 to advertise the Launching Pad Drive-In restaurant, the fiberglass spaceman capitalized on America's space race excitement. The Gemini program was sending astronauts into orbit, and roadside America responded with space-themed attractions.
The Gemini Giant belongs to a family of "Muffler Men"âoversized fiberglass figures mass-produced in the 1960s to advertise businesses. While most were destroyed or removed, the Gemini Giant survived because Route 66 preservationists recognized its cultural value. Though the Launching Pad Drive-In closed in 2019, the Gemini Giant remains, carefully maintained by the property owner. Visitors pull into the lot daily to photograph this green giantâa symbol of Route 66's playful, optimistic era.
Braidwood: Coal Mining Heritage Meets Route 66
Polk-a-Dot Drive In (1956-Present)
Location: 222 N Front St, Braidwood, IL 60408
Status: â
Still operating (seasonal)
The Polk-a-Dot Drive In has served hot dogs, burgers, and ice cream to Route 66 travelers since 1956. Its name comes from the distinctive polka-dot pattern painted on the buildingâa cheerful design meant to catch drivers' eyes. During Route 66's peak years, the Polk-a-Dot was one of hundreds of small family-run drive-ins feeding travelers. Now it's one of the few survivors, operating seasonally from March through October.
What makes the Polk-a-Dot special isn't just longevityâit's authenticity. The menu hasn't changed much in 70 years: Chicago-style hot dogs, hamburgers, hand-dipped ice cream cones, and root beer floats. The staff still serves walk-up customers through outdoor windows, just as they did when Route 66 traffic was heavy. On summer evenings, classic car clubs gather in the parking lot, recreating the scene that played out here in 1965, 1975, and 1985.
Dwight: A Perfectly Preserved Route 66 Town
If you visit only one town on Illinois Route 66, make it Dwight. This small community (population 4,000) has preserved its Route 66 heritage better than anywhere else in the state, maintaining multiple historic buildings and landmarks from the highway's golden age.
Ambler's Texaco Station (1933)
Location: 101 W Waupansie St, Dwight, IL 60420
Status: â
Restored as visitor center
Ambler's Texaco Station is architectural perfectionâa textbook example of 1930s gas station design. Built in 1933 by Standard Oil, the station features the distinctive "domestic style" architecture that oil companies promoted to make service stations blend into residential neighborhoods. The building's cottage-like appearance, with its red tile roof and white stucco walls, represented a deliberate move away from industrial-looking gas stations.
The station operated continuously until 1999, pumping gas for 66 years. When it closed, preservationists recognized its rarityâmost gas stations from this era were demolished decades ago. The village of Dwight purchased the building, restored it to 1930s condition, and now operates it as a Route 66 visitor center. You can walk inside and see the restored office, examine vintage gas pumps, and pick up maps for Route 66 attractions throughout Illinois.
Dwight Windmill (1896)
Location: E Chippewa St, Dwight, IL 60420
Status: â
Still standing
Long before Route 66, this Dutch-style windmill served Dwight's agricultural community, pumping water for livestock. When Route 66 came through town in 1926, the windmill became a landmark that travelers used for navigation. While not built for Route 66, the windmill represents the agricultural heritage that the highway intersected with across rural Illinois.
Pontiac: The Route 66 Hall of Fame
Illinois Route 66 Hall of Fame & Museum
Location: 110 W Howard St, Pontiac, IL 61764
Status: â
Open to visitors
Housed in Pontiac's former fire station, the Illinois Route 66 Hall of Fame & Museum is the most comprehensive collection of Route 66 artifacts in the state. Founded by Route 66 historian Bob Waldmire (himself a Route 66 legend), the museum displays vintage signs, photographs, postcards, and memorabilia documenting the highway's history through Illinois.
The museum's collection includes original neon signs rescued from demolished motels, hand-painted billboards from roadside attractions, and extensive photographic documentation of Route 66 businesses before they closed. Interactive exhibits explain how Route 66 was built, why the interstate system replaced it, and how preservation efforts have saved what remains. The Hall of Fame honors individuals who contributed to Route 66's legacy, from highway engineers to diner owners who served travelers for decades.
Pontiac-Oakland Automobile Museum
Location: 205 N Mill St, Pontiac, IL 61764
Status: â
Open to visitors
Appropriately located in a town named Pontiac, this museum showcases the automobiles that traveled Route 66âspecifically Pontiac and Oakland cars manufactured from 1907 to 2010. The collection includes beautifully restored vehicles from every decade of Route 66's existence, providing a rolling timeline of American automotive history. Seeing these cars helps visitors understand what Route 66 travelers actually droveâfrom 1930s sedans to 1960s muscle cars to 1970s station wagons.
Walldogs Murals
Location: Throughout downtown Pontiac
Status: â
Visible year-round
Pontiac has embraced Route 66 tourism by commissioning over 30 large-scale murals throughout downtown, many depicting Route 66 themes. These vibrant "ghost sign" style murals are painted by the Walldogs, a group of artists who specialize in traditional hand-painted advertising. The murals reference vintage Route 66 imagery, local history, and mid-century Americana, turning Pontiac into an open-air gallery.
Bloomington-Normal: Lincoln's Territory
Steak 'n Shake (1934 - Original Concept Location)
Location: Multiple locations (original at Normal)
Status: â
Chain still operating
Gus Belt founded Steak 'n Shake in Normal, Illinois, in 1934, just as Route 66 traffic was increasing. Belt's innovation was simple: grind the steak in front of customers to prove freshness, then hand-form burgers and cook them to order. The "steakburger" concept, combined with hand-dipped milkshakes, made Steak 'n Shake an instant hit with Route 66 travelers.
The chain expanded along Route 66 and beyond, becoming a Midwestern institution. While the original Normal location no longer exists, Steak 'n Shake restaurants still serve the same steakburgers that 1930s Route 66 travelers enjoyed. The chain's classic black-and-white tile design and table-side service evoke the era when Route 66 was America's Main Street.
Funks Grove: Pure Maple "Sirup"
Funks Grove Pure Maple Sirup
Location: 5257 Old Route 66, Shirley, IL 61772
Status: â
Still producing (seasonal)
Funks Grove has been tapping maple trees and making syrup since 1824âa full century before Route 66. When the highway came through in 1926, the Funk family began selling their maple "sirup" (they spell it the old way) to travelers from a small roadside stand. This became a Route 66 tradition: stop at Funks Grove, buy a bottle of pure maple sirup, and taste Illinois history.
The operation remains family-owned and decidedly old-fashioned. The Funks still tap trees by hand each February and March, boil sap using traditional methods, and bottle the syrup in glass containers. The stand operates only during sapping season and sells out quickly. This is Route 66 at its most authenticâa genuine family business that predates the highway and has survived its decline.
Springfield: The Heart of Route 66
Springfield holds sacred status for Route 66 enthusiasts. As Illinois' capital and Abraham Lincoln's hometown, Springfield was already a significant city when Route 66 was designated in 1926. In fact, Springfield businessman John Woodruff worked with Cyrus Avery to plan the route, and the first Route 66 shield was planted in Springfield. The city embraced its Route 66 identity, and today maintains more original Route 66 sites than any other Illinois city.
Cozy Dog Drive In (1949)
Location: 2935 S 6th St, Springfield, IL 62703
Status: â
Still operating
Ed Waldmire invented the "Cozy Dog" in 1949âa hot dog on a stick, dipped in batter and deep-fried. The concept wasn't entirely new (corn dogs existed), but Waldmire perfected the recipe and coined the name "Cozy Dog." He opened the first Cozy Dog Drive In on Route 66 in Springfield, and it became an instant Route 66 institution.
The Cozy Dog represents Route 66 roadside food culture at its finest: a unique menu item, quick service, affordable prices, and a family-run business. Ed's son Buz ran the restaurant for decades, becoming a Route 66 ambassador who mentored preservationists and welcomed travelers. Today, the third generation operates the Cozy Dog, serving the same recipe Ed perfected in 1949. The walls display Route 66 memorabilia, vintage photographs, and tributes to the Waldmire family's contributions to Route 66 preservation.
Route 66 Drive-In Theater
Location: 1700 Recreation Dr, Springfield, IL 62702
Status: â
Still operating (seasonal)
Drive-in theaters and Route 66 go hand-in-handâboth represent postwar American car culture. The Route 66 Drive-In Theater opened in 1949 and has operated continuously since, making it one of America's oldest surviving drive-ins. During Route 66's heyday, families traveling the highway would stop in Springfield, check into a motor court, grab Cozy Dogs for dinner, and catch a double feature at the drive-in.
The theater has been lovingly maintained and upgraded with digital projection while preserving its vintage character. The giant screen, the playground beneath it, and the art deco marquee remain from the original 1949 construction. Operating from April through October, the drive-in shows current movies but maintains its mid-century atmosphereâa perfect example of Route 66 heritage adapting to modern times.
Shea's Gas Station Museum (1934)
Location: 2075 Peoria Rd, Springfield, IL 62702
Status: â
Restored as museum
Bill Shea built this Marathon gas station in 1934 and operated it for 60 years, serving generations of Route 66 travelers. When Bill retired in the 1990s, Route 66 preservationists convinced him to donate the station for preservation rather than demolition. Today, it operates as a museum showcasing 1930s gas station architecture, complete with vintage pumps, oil company signage, and period automobiles.
Maldaner's Restaurant (1884)
Location: 222 S 6th St, Springfield, IL 62701
Status: â
Still operating
Maldaner's predates Route 66 by 42 years but became a favorite dining spot for travelers seeking a sit-down meal rather than roadside fare. Opened in 1884, Maldaner's is Illinois' oldest restaurant, serving Continental cuisine in an elegant downtown setting. During Route 66's golden age, travelers who wanted to escape hamburger joints and diners would dress up and dine at Maldaner's, enjoying white tablecloth service in Springfield's historic downtown.
Auburn: Brick Road Perfection
Brick Section of Original Route 66
Location: Auburn, IL 62615
Status: â
Preserved and drivable
Between Auburn and Virden, a 1.4-mile section of original Route 66 remains paved with bricksâone of the few surviving brick stretches of the entire 2,448-mile highway. Laid in 1932, these bricks represent the transition from dirt roads to paved highways. Driving this section provides a visceral connection to Route 66's past: the rhythmic bump-bump-bump of tires on brick, the narrow two-lane width, and the absence of modern highway features like shoulders or guardrails.
This section survives because it was bypassed early (in 1940) by a new alignment, and the town of Auburn refused to pave over it. Today, it's a pilgrimage site for Route 66 enthusiasts who want to experience original pavement from the highway's early days.
Litchfield: Route 66 Museum & Café
Ariston Café (1935)
Location: 413 Old Route 66, Litchfield, IL 62056
Status: â
Still operating
The Ariston Café has fed Route 66 travelers since 1935, making it one of the oldest continuously operating restaurants on the entire route. Pete Adam built the original Ariston in Carlinville in 1924, but when Route 66 was realigned away from Carlinville in 1935, Pete dismantled the entire building, moved it to Litchfield, and reopened on the new alignment. This move exemplifies the economic reality of Route 66: being "on the highway" meant survival; being bypassed meant bankruptcy.
The Ariston's longevity stems from consistent quality and family dedication. Three generations of the Adam family have operated the restaurant, maintaining the same menu philosophy: homemade food, generous portions, fair prices. The dining room retains its 1930s character with wood paneling and vintage signage. The Ariston became so iconic that it appears in numerous Route 66 guidebooks and documentariesâyet it remains a working restaurant serving daily customers, not a museum piece.
Sky View Drive-In (1950)
Location: 1500 Old Route 66 N, Litchfield, IL 62056
Status: â
Still operating (seasonal)
The Sky View opened in 1950 and represents the second generation of drive-in theatersâlarger screens, better sound, and purpose-built for the postwar automobile boom. Like Springfield's Route 66 Drive-In, the Sky View provided entertainment for Route 66 travelers and became a community gathering place for Litchfield residents. The theater has been continuously operated by the same family since opening, recently upgraded to digital projection while maintaining its vintage atmosphere.
Staunton: Henry's Rabbit Ranch
Henry's Rabbit Ranch
Location: 1107 Historic Old Route 66, Staunton, IL 62088
Status: â
Open as roadside attraction
Henry's Rabbit Ranch is exactly what it sounds like: a rabbit ranch along Route 66, filled with vintage Volkswagen Rabbits and actual rabbits. Rich Henry created this quirky roadside attraction in the 1990s as a tribute to Route 66's tradition of unusual stops meant to entertain travelers and encourage them to pull over.
The site features dozens of old VW Rabbits in various states of decay, rabbit hutches with live rabbits, Route 66 memorabilia, and a small gift shop. It's intentionally kitschyâa modern version of the "see the world's largest ball of twine" attractions that dotted Route 66 in its heyday. Henry's represents Route 66's playful spirit and proves that the highway's culture of roadside oddities continues.
Collinsville: World's Largest Catsup Bottle
Brooks Catsup Bottle Water Tower (1949)
Location: 800 S Morrison Ave, Collinsville, IL 62234
Status: â
Still standing (no longer functional)
Standing 170 feet tall, the World's Largest Catsup Bottle is exactly what Route 66 roadside Americana is all about: big, bold, impossible to miss, and utterly unnecessary. Built in 1949 by the W.E. Caldwell Company to advertise Brooks Catsup, this water tower served the G.S. Suppiger catsup bottling plant. The design was meant to catch drivers' eyes on Route 66, which ran nearby.
When the bottling plant closed in 1960, the water tower was slated for demolition. Preservationists formed the Catsup Bottle Preservation Group and raised funds to restore and maintain it as a historic landmark. The tower was repainted to its original 1949 appearance and now serves as Collinsville's most recognizable landmark. It represents the intersection of advertising, architecture, and Route 66's visual cultureâa time when businesses competed for highway drivers' attention with increasingly spectacular roadside structures.
Chain of Rocks Bridge: The Illinois-Missouri Crossing
Old Chain of Rocks Bridge (1929)
Location: 10800 Riverview Dr, Madison, IL 62060
Status: â
Open to pedestrians/cyclists
The Chain of Rocks Bridge marked Illinois' western boundary on Route 66, carrying travelers across the Mississippi River into Missouri from 1929 to 1967. The bridge is famous for its unusual 22-degree bend at the middleâa design necessitated by the river's strong current and rocky bottom (the "chain of rocks" that give the bridge its name). This bend made the bridge memorable; travelers approaching from either direction suddenly turned sharply mid-span.
When the new Chain of Rocks Bridge opened in 1967, the old bridge closed to vehicular traffic and faced demolition. But in 1999, after decades of abandonment, the bridge was restored and reopened as a pedestrian and bicycle path. Today, you can walk across the Mississippi River on original Route 66 pavement, experiencing the same view that millions of travelers saw from 1929 to 1967. The restored bridge includes interpretive signs explaining its history and Route 66 significance.
Traveling Route 66 Today: Practical Information
Following the Route
Route 66 through Illinois is well-marked with brown "Historic Route 66" signs, making navigation relatively easy. However, multiple alignments exist because the highway was relocated several times between 1926 and 1977. The most commonly followed route is the 1940-1977 alignment, which provides the best preserved landmarks and businesses.
For detailed turn-by-turn navigation, consult the EZ66 Guide for Travelers by Jerry McClanahan, which provides mile-by-mile directions for all eight Route 66 states. The Illinois Route 66 Scenic Byway offers downloadable maps and GPS coordinates for major attractions.
How Long Does It Take?
Driving the entire 301 miles of Route 66 through Illinois takes approximately 6-8 hours without stops. However, to truly experience Route 66, plan for 2-3 days. This allows time to visit museums, eat at historic diners, photograph landmarks, and explore small towns. Many Route 66 enthusiasts break the journey into segments:
- Day 1: Chicago to Pontiac (90 miles) - Lou Mitchell's, Joliet, Wilmington, Dwight, Pontiac museums
- Day 2: Pontiac to Springfield (100 miles) - Funks Grove, Lincoln sites, Springfield attractions
- Day 3: Springfield to Chain of Rocks (111 miles) - Auburn bricks, Litchfield, Collinsville
Best Time to Visit
Spring through fall (April-October) is ideal for Route 66 travel in Illinois. Many seasonal businesses, including drive-ins and roadside stands like Funks Grove, operate only during warmer months. Summer weekends bring car shows and Route 66 festivals in towns like Pontiac and Springfield. Fall offers beautiful foliage and fewer crowds.
Avoid winter if possible. Illinois winters are harsh, some attractions close, and snow-covered Route 66 landmarks lose their visual appeal. However, hardcore Route 66 enthusiasts appreciate the solitude and off-season authenticity of winter travel.
Where to Stay
While most vintage Route 66 motor courts have closed, a few survive:
- Soulsby Service Station (Mount Olive) - Restored station with vintage ambiance
- Best Western Lincoln Inn (Lincoln) - Modern hotel with Route 66 theme
- Route 66 Hotel & Conference Center (Springfield) - Modern hotel celebrating local Route 66 heritage
For authenticity, consider staying in restored downtown hotels in Joliet, Pontiac, or Springfield. These historic properties existed during Route 66's heyday and have been renovated while maintaining period character.
The Future of Route 66 in Illinois
Illinois has embraced Route 66 preservation more enthusiastically than most states. The Illinois Route 66 Scenic Byway, established in 2005, provides state support for maintaining and promoting Route 66 sites. Local communities like Pontiac and Dwight have built their tourism economies around Route 66 heritage, ensuring ongoing maintenance and interpretation.
However, challenges remain. Original Route 66 businesses continue to close as owners retire and buildings deteriorate. Gas stations, motels, and diners that survived the interstate era now face 21st-century economic pressures. Preservationists work constantly to document endangered sites, raise funds for restoration, and convince communities that Route 66 heritage has economic value.
The good news: Route 66 tourism continues growing. Each year, thousands of domestic and international travelers drive the Mother Road, spending money in small towns that the interstate bypassed decades ago. This tourism provides economic incentive for preservation. As long as people want to experience Route 66's history, Illinois communities have reason to maintain their landmarks, restore their signs, and keep their diners open.
Conclusion: Why Route 66 Still Matters
Route 66 through Illinois tells the story of 20th-century America: economic expansion, automobile culture, small-town entrepreneurship, migration, and ultimately, obsolescence and preservation. The highway's rise and fall mirrors larger American trendsâthe optimism of the 1920s, the desperation of the 1930s Dust Bowl, the prosperity of postwar America, and the efficiency-focused interstate era that made Route 66 obsolete.
What survives in Illinoisâthe neon signs, the brick pavement, the family-run dinersârepresents more than nostalgia. These sites preserve a time when travel was slower, when the journey mattered as much as the destination, and when American communities were connected by a single ribbon of concrete stretching from Chicago to Los Angeles.
Driving Route 66 today requires deliberate effort. You must exit the interstate, follow two-lane roads through small towns, and seek out landmarks that don't advertise with interstate billboards. But that effort is rewarded with authentic encounters with American historyânot packaged or commercialized, but preserved by communities who remember when Route 66 was their Main Street.