Route 66 - Day #1
Saturday, April 11, 2026
First stop is downtown Chicago before setting out on the route.
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From ChatGPT:
Cloud Gate, commonly called “The Bean,” is a reflective stainless steel sculpture in Millennium Park, Chicago. Designed by Anish Kapoor and unveiled in 2006, it mirrors the city skyline and visitors, creating interactive, distorted reflections. Its seamless surface and iconic form make it one of Chicago’s most photographed landmarks and a symbol of the city’s modern identity.
Panorama to include the Chicago skyline and Cloud Gate.
Cloud Gate is a fascinating art piece that interacts well with its surroundings. Here the city skyline is reflected on the surface.
The first of MANY Route 66 shields on this trip! This one is directly across from the Art Institute of Chicago.
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Of all the shields we will encounter, this one, and the one at the Santa Monica Pier, are probably the two most important. This sign is the “official” start of the route and we will drive past it headed west leaving downtown.
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The journey begins!
Just down the street is another sign claiming the start of Route 66. However, the previous one is the one everyone accepts as the beginning.
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From ChatGPT:
Buckingham Fountain in Grant Park is one of the largest fountains in the world. Dedicated in 1927 and inspired by Latona Fountain, it features elaborate water displays and evening light shows, symbolizing Lake Michigan and surrounding states, and remains a centerpiece of Chicago’s lakefront.
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Both ends of Route 66 start/end with a large body of water. Here is Lake Michigan and if all goes well, twenty days from now we will reach the other large body of water - the Pacific Ocean.
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Headed back to the car, we came across this arch from the front of the old Chicago Stock Exchange.
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Just outside of downtown, this mural is a tribute to the 100th anniversary of Route 66 this year.
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From ChatGPT:
“Castle Car Wash” is a castle-like structure on Chicago’s South Side long rumored to have been a hideout for Al Capone. Built in the early 20th century, its fortified design fueled speculation. Though colorful, historians find little evidence supporting the Capone connection, making it more legend than verified history.
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From ChatGPT:
Hofmann Tower, located in nearby Lyons, Illinois, was built in 1908 as part of a riverside recreation complex by George Hofmann. Overlooking the Des Plaines River, it once drew crowds for picnics and leisure, and today stands as a restored historic landmark reflecting early 20th century social life.
Fabulous McCook in the fashion of the iconic Las Vegas sign.
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From ChatGPT:
Dell Rhea's Chicken Basket is a historic roadside eatery along Route 66, famous for its fried chicken and nostalgic charm. Originating as a 1930s gas station lunch counter, it expanded into a full restaurant in 1946, becoming a beloved stop for travelers and a preserved symbol of classic American road culture.
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Inside Dell Rhea's Chicken Basket. Because Lisa doesn’t eat chicken, we ordered the giant pretzel. Well, like many things on Route 66, GIANT was an understatement!!
From ChatGPT:
Dick’s Towing Service, often called “Dick’s on 66,” is a longtime auto repair shop and towing company along historic Route 66 in Joliet. Known for reliable roadside assistance and mechanical service, it has served motorists for decades and remains a practical stop tied to the working heritage of the Mother Road.
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Standing on some original Route 66 bricks.
Illinois - and Joliet specifically - are very proud of Jake and Elwood. You MIGHT see them again in future photos. Here they are atop Rick & Creamy Ice Cream shop.
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Route 66 Park in Joliet, IL.
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Our next stop was the Joliet Area Historical Museum.
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This exhibit shows the entirety of our route. We still have a few miles to go!
Where have we seen these guys before? But wait, there may be more sightings to come….
Lisa added our names and date to the shield. Hint - look in the white circle of the first six.
From ChatGPT:
Rialto Square Theatre in Joliet opened in 1926 as an ornate vaudeville movie palace. Known as the “Jewel of Joliet,” its lavish Neo-Baroque design and grand interiors rival larger city theaters. Restored in the 1980s, it now hosts concerts, plays, and events, remaining a centerpiece of the city’s cultural and architectural heritage.
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From ChatGPT:
The Bluesmobile on a stick in Joliet is a quirky Route 66 landmark, referencing The Blues Brothers and celebrating the city’s cinematic connection.
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The movie quote associated with this vehicle.
Next stop, Wilmington, IL - home of the Gemini Giant!
For frame of reference, I stood next to him and my head comes to the level of his knee.
From ChatGPT:
The Gemini Giant is a 30-foot fiberglass “Muffler Man” in Wilmington along Route 66. Built in the 1960s, it features a space helmet and rocket, symbolizing the space age. Originally advertising a drive-in, it now stands as a beloved roadside icon and photo stop.
The Polk-A-Dot Drive Inn features several larger than life fiberglass characters to take your photo with.
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Not these characters again!!
This is known as The Shop on Route 66 and is a souvenir shop in Gardner, IL. Unfortunately, it had already closed by the time we got to town.
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This art work is located at The Shop on Route 66 and depicts the eight states on the route with a shield and license plate from each of them.
Also in Gardner is the two-cell jail. From the number of penal institutions we have seen on this trip, one would think Illinois has more than it’s share of criminals.
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From ChatGPT:
The Riviera Restaurant (often just called the Riviera site today) is now associated with the preserved streetcar diner exhibit next to the historic two-cell jail in Gardner. It is not a traditional standalone operating restaurant anymore.
Inside the diner.
The Ambler Texaco Gas Station in Dwight, IL.
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From ChatGPT:
Ambler’s Texaco Gas Station in Dwight is a restored 1933 “house-and-canopy” style service station along historic Route 66. Operated for decades by Basil “Tubby” Ambler, it fueled travelers until 1999. Today it serves as a visitor center and museum, showcasing 1940s-era restoration and the golden age of roadside automobile culture.
This is fascinating to consider; when Route 66 was in its prime, they had to install this tunnel system to get pedestrians safely between the school on one side of the street and the church on the other. Traffic was so heavy that simply crossing the road became dangerous enough to warrant this tunnel. The day I took this photo not a single car went by and I could have stood in the road for who knows how long before even a single vehicle passed. Read the plaque for details.
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From ChatGPT:
The Standard Oil Gas Station in Odell, Illinois is a restored 1932 “house-and-canopy” style service station along historic Route 66. Built by Patrick O’Donnell, it originally sold Standard Oil fuel and later other brands before becoming a repair shop. Closed in the 1970s, it was restored and now serves as a visitor center celebrating classic roadside travel culture in small-town Illinois.
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