Explore the Best Stops on Illinois Route 66 Adventure

Route 66 spans an impressive 2,448 miles, winding from the iconic Chicago Pier to the picturesque Santa Monica Pier. That’s quite a distance to cover! Therefore, I’ve chosen to divide my articles on this remarkable journey into smaller, digestible segments—highlighting the “best, most fun, quirkiest, and most accessible” attractions along the way. Additionally, I plan to include some intriguing fun facts and trivia to enrich (I hope) your reading experience!

First up – Illinois. To plan your trip through Illinois, you may wish to check out the list of events here.

So let’s begin! Since we embarked on our journey in Chicago, I will begin by detailing our experience with Illinois ( an impressive 301 miles of Route 66). I will only include the locations where my travel companion, Marji, and I made our stops.

Here’s my first tip for this blog: If you have the time and energy, feel free to venture beyond our itinerary. We wish we could have stopped at every suggested town and venue. Sadly, it was impossible. You, however, can do what you wish- so enjoy creating your own adventure!

CHICAGO

Chicago’s Navy Pier is where it all begins if you are traveling east to west. Marji and I had visited the Pier in preparation for our trip during the Summer of 2024. Highlights of the Pier included hopping aboard the tall ship, The Windy. I was even allowed to become “crew” – what a blast!

And, don’t forget to take a photo of the starting point for Route 66. You will find it here >> 600 E Grand Ave, Chicago (Google Maps locator).

A view of the Chicago skyline from the water, featuring the Cloud Gate sculpture, several tall skyscrapers, and vibrant flags on a historic building in the foreground. — Chicago’s Nave Pier – photographed from the tall ship- THE WINDY

Joliet, Illinois

We “officially” began our Route 66 tour in Joliet by searching for the Blues Brothers sculpture that was purportedly to be found outside the Old Joliet Prison. We came up empty at that location! If you are curious, you can watch a clip of the scene from the movie here to understand the relevance.

And, despite being too late for the tour of the prison, we were able to scour the area for much Blues Brothers-related memorabilia. We found the dynamic duo atop an ice cream shop and a mural of them on a nearby street. (Trivia: The Blues Brothers were played by NBC TV Saturday Night alumni – John Belushi and Dan Akroyd).

Historic prison building with stone architecture, featuring tall towers and security fences against a blue sky.

A Route 66 sign with a classic design featuring bold colors, positioned atop a roof, accompanied by a statue of a man in a suit and hat, against a clear blue sky.

A mural featuring two characters in sunglasses, with a police car and a distant figure in the background, under the text 'WE'RE ON A MISSION FROM GOD'.

The Illinois Rock and Roll Museum on Route 66

A colorful, oversized guitar sculpture with vibrant patterns, including a pink and yellow neck and a striped body featuring various artistic designs. It stands on a decorative base in a music-themed exhibition setting.

A vintage jukebox in a Route 66 themed soda bar, featuring retro decor, a bar with chrome stools, and framed music memorabilia on the walls.

This is a small museum located downtown in Joliet. It is a good place to pop in, learn about Illinois music artists (such as Burl Ives, Nat King Cole, Alison Krauss, among many others). You will find options to listen on the road via their podcast, and music education opportunities are available.

TIP: There is a passport stamp book available to enhance your Route 66 experience. You can find more about the book and other support materials here. In addition, Illinois has its own Route 66 Centennial passport book. We got ours free. Ask for one at any of the official stops.

The Joliet Historical Museum

Sadly, this highly touted museum was closed when we arrived in Joliet. Not to worry – the outside sculptures were worth a few minutes of our time. To be sure you don’t make our mistake and miss the opportunity to visit and check out their website before heading over.

Large white 3D numerals '66' next to a black and white Route 66 sign, set against a brick wall and modern window.

Welcome sign for Route 66 in Joliet, Illinois, featuring a map of the historic route along with informational texts about attractions and landmarks.

Other great Route 66 attractions in Joliet:

A large, colorful postcard-style sign that reads 'Greetings from JOLIET, ILL.' featuring images of various landmarks and scenery from Joliet, Illinois.

The Route 66 Park – This is a beautifully designed park featuring numerous sculptures and inviting spaces to relax or enjoy a leisurely walk. It appeared to be wheelchair accessible.

The Rialto Square Theater was closed the day we found ourselves in Joliet. However, I was able to snap a few photos of the lobby through the main front doors. I could tell this was a very handsome theater and one I wished I could have explored more closely. (Trivia: For those of you from San Pedro, California- this theater had a similar vibe to the distinguished Warner Grand Theater.)

Facade of a theater featuring ornate architecture and a marquee announcing 'The Perondi's Stunt Dog Experience' on April 9 at 6:30 PM.

Interior view of a grand hall with polished marble floors, ornate ceiling decorations, and chandeliers, featuring empty tables and a volunteers' table in the background.

Interior view of an ornate theater entrance featuring a vintage box office kiosk with a wooden and black marble design, surrounded by decorative ceiling details and double doors leading outside.

Facade of a historic theater building featuring ornate architectural details and a marquee displaying upcoming events.

A plaque describing the 'Mother Nature' sculpture in Joliet, featuring a life-size bronze figure of a female surrounded by a colorful mosaic. The plaque highlights the sculpture's significance in representing the history of farming and its cultural context.

View of historical signage overlooking a landscape with trees and a water tower in the background, under a clear blue sky.

A bronze statue of a female figure seated in a contemplative pose on a colorful mosaic pedestal against a clear blue sky.

WILMINGTON

Wilmington, Illinois, is the home of 1964 created GEMINI GIANT. He was also one of the first GIANTS that we encountered on Route 66. Found in a “random” park in Wilmington, it looked far above the people who came to view it! Marji and I met the nicest couple who were out for their morning walk. They stopped to tell us about the historical society’s plans for the Route 66 centennial celebration and how excited they were to be participating with this group. They were simply lovely, and honestly, I felt that we were making a “Best of Americana” commercial. Read more about this 30-foot-tall Gemini Giant here.

DWIGHT

Dwight is a charming little town. We stopped at a local supermarket and were impressed with the eclectic selection of ethnic foods. Dwight’s visitor bureau has put together a list of their Route 66 attractions, and without a doubt, my favorite was the gas pumps found at the Ambler’s Texaco Gas Station.

PONTIAC

Pontiac was jam-packed with activities intended to keep Route 66 visitors busy for hours! They are family-friendly, interesting, mostly accessible, educational, and fun!

First, take a walk through the town following the blue footprints on the sidewalk. You will find many murals created along the path. The majority was painted by the Route 66-renowned artist, Bob Waldmire.

The video below is of one of the murals painted by Bob Waldmire. It is located in Pontiac just steps from their main Route 66 Museum.

ROUTE 66 ASSOCIATION of ILLINOIS

Signage for Historic Downtown Pontiac, indicating directions to the War Museum and highlighting Route 66 and Titanic exhibits.

Meet Rose. She was the docent who greeted us at the Route 66 Association of Illinois museum. She could have regaled us with stories about Route 66 for hours! At 88 years young, she was sharp as a tack!

An elderly woman in a pink shirt holds an aerial view poster of the District State Police Headquarters, standing in front of a glass display case filled with historical photographs and artifacts. — Rose showed us the diagram of the local police station

A shop window display featuring a vintage theme, with various memorabilia related to Route 66, including signs, badges, and old newspapers. The window shows an 'OPEN RT 66' sign and items like a cooler and a drawing of two characters on a motorcycle. — Rose showed us the diagram of the local police station

The building that houses this museum also offers an inside look into the Illinois military and a local connection to the Titanic. The displays are positioned in close quarters, making maneuvering a bit tricky. An elevator and captioned videos are available.

ATLANTA, ILLINOIS, LOVES GIANTS!

These GIANTS are a lot of fun! I’d rate the FUN FACTOR at 7/10. But why are they iconic along Route 66? I learned that they were made in the 1960s and 70s from fiberglass and called “Muffler Men.” Atlanta, Illinois, has a notable collection of these GIANTS. The Route 66 American Giants Museum features one of the largest collections. The museum is easily accessible, well-signposted, and offers various photo opportunities. Entry is free; however, donations are appreciated.

But, wait! Don’t stop at only the GIANTS. Discover more of Atlanta here.

A collection of large decorative statues in a display area, featuring characters like a chef, a girl, a cowboy, and a rooster, with one statue wearing checkered overalls and holding a weight aloft. — American Giants Museum in Atlanta, Illinois

View of a brick wall with a sign for 'Atlanta Park' on Route 66, featuring a clock tower and a building in the background against a blue sky. — American Giants Museum in Atlanta, Illinois

SPRINGFIELD

TIP: There is much history and Route 66 attractions to do and see in Springfield. I would start by reviewing their comprehensive online guide.

The capital of Illinois is Springfield. Within its city limits, you will discover many fascinating places to visit. Due to time constraints, we focused on the State Capitol building and the family home of Abraham and Mary Todd Lincoln. We also passed by several “66” commemorative signs that caught our attention. Once again, I wish we had spent more time exploring, and I recommend that serious travelers consider slowing down to visit the many attractions in Springfield with more appreciation.

Related: Museums of Springfield

The state capitol is beautiful. The grounds have a touching exhibit: a mosaic wall of names on ceramic pieces. This mural radiates warmth and captures the spirit of Route 66 – Community! The mosaic is easily accessible due to its outdoor location near the building. Braille is featured.

A colorful mosaic wall made of variously shaped and textured tiles in bright hues of yellow, red, green, and blue, with patterns resembling waves and circles.

Colorful mosaic wall featuring an array of textured stones and materials, showcasing various colors and patterns. — The rotunda of the Illinois Satte Cap;itol

A plaque with braille text mounted on a textured wall. — The rotunda of the Illinois Satte Cap;itol

ILLINOIS ROUTE 66 – THE LAND OF LINCOLN

A yellow Victorian-style house with green shutters and a front porch, surrounded by a white picket fence and a landscaped yard.

The homestead of our 16th president, stands in stark contrast to the contemporary buildings that line the streets. It’s a curious sight to see modern coffee shops alongside a place that provided comfort to a family so significant in American history. This beautiful old home is surprisingly unassuming. The tree-lined streets are shared with other visitors, and there is a parking lot adjacent to the main museum building, with a nominal parking fee. Arriving early is advisable, as I anticipate that school groups and vacationing families will flood the area during the peak visiting season.

Note: Although accessible, the road is rough and the sidewalks a bit uneven.

A two-story historical house with wooden siding, featuring green shutters and a brown door, surrounded by a decorative fence and steps leading to the entrance.

Sign about economic and ethnic diversity in Springfield, featuring historical maps and census data from the 1860s, discussing the demographics of residents including African Americans, Irish, German, Portuguese, and various occupations.

CHATHAM’S SUGAR CREEK COVERED BRIDGE

We ended our stay in Illinois with a special trip to the Sugar Creek Covered Bridge. Serene. Picturesque. Worth the visit. (click for the map location)

A scenic view of a paved path leading to a red covered bridge, surrounded by trees and greenery.

View from inside a covered bridge, showing wooden beams and an open space leading to a path flanked by trees.

View from inside a covered bridge, showing wooden flooring and an opening towards a path lined with trees.

Last thoughts about Illinois Route 66

Illinois is a big state. Consider allocating more than a day on your itinerary to explore.
Plan by checking out the event schedules for each location you wish to visit.
There are plenty of opportunities for family fun. Don’t forget to obtain the Illinois Route 66 passport book!
ACCESSIBLITY: Overall, signage is good, access for those with mobility challenges ranges from excellent to fair. Families with children with Autism may enjoy the various sensory activites and parks made available. Captioned videos were not always apparent.
Food recommendation: Joliet has a lovely Hispanic community and we found numerous restaurants with authentic Mexican cuisine.
ENJOY!

And, I know I missed some great Route 66 Illinois spots – let me know some of your favorites!