Nostalgic Journey: Chicago to Pontiac on Historic Route 66’s First 100 Miles

When we think of the glory of mid-century America, we often think of historic Route 66. The original route was 2,448 miles (3,940 Kilometers) from downtown Chicago, IL to the Santa Monica Pier in California. It is a road trip everyone should take – at least a portion of it is accessible to all. 

If you want to take a nostalgic journey, consider the First Hundred Miles of historic Route 66 from Chicago to Pontiac, Illinois. It is an easy drive and doable in a few days.

Filled with great museums on Route 66, along with little restaurants, national historic sites, and a giant green spaceman (more on that later), it may pique your interest enough to drive the rest of the historic route on the Mother Road. I bet you didn’t know this fun fact: In the classic novel The Grapes of Wrath, John Steinbeck christened Route 66 the Mother Road, and it has carried that moniker ever since.

Follow this road trip at the beginning of the midwest, stay a few nights in Chicago, then head down to Joliet and end your First Hundred Miles in Pontiac. 

Here is a detailed itinerary that motorists will enjoy of Route 66, covering all the highlights of the First Hundred Miles and the many Instagrammable locations in Illinois along the way.

Day 1 – Chicago

Millenium Park and Buckingham Fountain

Buckingham Fountain in chicago
Photo Credit: DownshiftingPRO.

There is no shortage of things to do in The Windy City. You can take a boat tour to view the beautiful architecture or walk down the Magnificant Mile and shop. I suggest a stop at the Art Institute of Chicago (AIC) to see some iconic art.

If that is not your jam, take a walk around Millenium Park, which is adjacent to the AIC. Take a selfie by ‘The Bean’ or watch the faces change on the tall fountains with images projected on the facade. 

Stroll through the park and check out some of the beautiful gardens, then stop at Buckingham Fountain. You will recognize the fountain from the opening credits if you watched Married with Children in the 1990s.

Museum Campus

Downtown Chicago is full of great museums, and it seems a shame to only talk about one, so we will narrow it down to an area called Museum Campus. You will find the Field Museum of Natural History, The Shedd Aquarium, and The Alder Planetarium here. 

The Field Museum opened in 1921 and is a central hub for research, educational and cultural programming, and environmental work. 

Want to come face-to-face with the world’s largest tyrannosaurus rex? Plan a visit to the Field Museum, where you can see the legendary dinosaur known as “Sue.” The Field’s stunning life-sized natural history exhibits and explore a revolving selection of special exhibits.

Historic Route 66 Begins Sign

historic route 66 sign
Photo Credit: DownshiftingPRO.

It all starts here at Adams Street and Michigan Avenue. There is no better way to commemorate the mother of all road trips than the Route 66 Begins sign in downtown Chicago. 

It is very close to the freeway and half a block from one of many museums on Route 66— including the Art Institute of Chicago – and is a starting line for photo ops on this epic, nostalgic journey.

Day 2 – Harvester Park

Harvester Park on historic route 66
Photo Credit: DownshiftingPRO.

A great family stop, Harvester Park is designed as a trip down Route 66, featuring roadside attractions and sights from all eight states the road passes through. 

The landmarks are reimagined with play in mind, from a tall slide in the shape of the Willis Tower to the iconic Blue Whale. This recreational area is a miniature interstate highway, monument, and Route 66 shield, making it a fun road trip stop.

Route 66 originally went past the southern border of Harvester Park, which is why the theme is so fitting. Route 66 enthusiasts will marvel at all the details woven in. Kids will love playing at such a unique and colorful playground while learning about the historic route.

Old Joliet Prison

Old JolietPrison
Photo Credit: DownshiftingPRO.

Take the self-guided walking tour talks and learn about the prison’s general history from when it first opened in 1858 to today. 

True to its historic legacy, the Old Joliet Prison now takes its rightful place as an authentic, unique asset, preserving a link to the history of the City of Joliet, and it continues to draw interest from visitors worldwide. 

If the front gates look familiar, you would have seen it in the opening scene of The Blues Brothers movie or parts of Prison Break.

Rialto Theater

inside the rialto theatre
Photo Credit: Heritage Corridor

Soon to be celebrating its 100-year anniversary, the Rialto Square Theatre (also known as the ‘Jewel of Joliet’) is a historic vaudeville and movie theatre. Considered one of the nation’s most beautiful theatres, this historic property has a memorable marquee. It is all part of American history you will want to see and commemorate. Shiny and bright, it lights up at night!

Joliet Route 66 Diner

truck inside diner
Photo Credit: DownshiftingPRO

What makes this a fun stop on this national route is that you will be transported back to a traditional diner. Heritage Travel reminds you of motels, bottomless cups of coffee, and large plates of comfort food. Have a look at the decorations and wall signs from the 1950s and 60s.

Illinois Rock & Roll Museum on Route 66

Illinois Rock and Rold Museum
Photo Credit: DownshiftingPRO

You won’t be able to miss the twenty-four-foot-tall guitar outside the Illinois Rock & Roll Museum on Route 66! This brand-new museum exists to preserve the history of musicians and bands with ties to Illinois (Chicago, Cheap Trick, Muddy Waters & REO Speedwagon – all Hall of Fame inductees) while educating visitors about the rich history of music. You can almost hear the song (Get Your Kicks) on Route 66 as you walk around and look at the memorabilia.

Joliet Area Historical Museum and The First 100 Miles Welcome Center

exhibit at joliet area historical museum
Photo Credit DownshiftingPRO

Located in the Joliet Area Historical Museum, The First Hundred Miles Welcome Center can help plan a road trip and is full of Route 66 souvenirs and gifts made by Illinois Makers. You can even find two movie-worn Blues Brothers suits in the museum lobby! 

There is also an exhibit and interpretive signs that illustrate the construction of the Michigan-Illinois Canal. Located a few miles from the center, the area remains a significant local historic district. This visitor center is an excellent introduction to the American Midwest and many national historic landmarks. 

The Gemini Giant

green gemini giant statue on historic route 66
Photo Credit: DownshiftingPRO

The Launching Pad Drive-In (temporarily closed) is the home of the Gemini Giant. Standing 30 feet tall, the Gemini Giant is a space-age “Muffler Man” and one of just a few still-standing statues on Route 66. 

Since 1964, he’s been keeping watch over cross-country road trip travelers with his bright green suit and silver rocket in hand. Great road-tripping photo-ops!

Polk-a-Dot Drive-in

interior of drive in
Photo Credit: DownshiftingPRO

The Polk-A-Dot Drive-In is a nostalgic 1950s-style roadside diner known for burgers, malts & ice cream. From their iconic signage to the retro interior and selfie-worthy pop culture statues outside, you’ll feel like you’ve traveled back in time on this great American road trip. 

Ambler-Becker Texaco Station

gas station exterior
Photo Credit: DownshiftingPRO

This historic 1933 service station was the longest-operating gas station along Route 66. Now, it serves as Dwight’s Welcome Center. Stop and chat with the knowledgeable volunteers, marvel over the artifacts preserved in the filling station, and don’t forget to sign the guestbook and put a pin in the maps on the wall. 

There is also a small gift shop for souvenirs. Along this US road trip, detours are a Route 66 shield and an old-style billboard for the perfect Instagrammable op of historical landmarks.

Route 66 Association of Illinois Hall of Fame and Museum

route 66 museum exterior
Photo Credit: DownshiftingPRO

Featuring the largest painted Route 66 shield mural on the side of the Route 66 Association of Illinois Hall of Fame and Museum, there are plenty of photo ops just outside of the museum. 

This museum features thousands of Route 66 artifacts and memorabilia, including Route 66 artist and icon Bob Waldmire’s bus and van.  

Murals on Mainstreet

murals on main st on historic route 66
Photo Credit DownshiftingPRO

The collection of 19 outdoor murals around the historic downtown was created in four days during the Walldog Summer Bash 2009. 

These vignettes of small-town life will remind you of historical buildings in a Norman Rockwell version of America in the 20th century – gas stations, diners, general stores, soda shops, etc. 

There are plenty of opportunities to pose within these murals to blend in with the story!

Pontiac-Oakland Auto Museum

interior of auto museum
Photo Credit: DownshiftingPRO

There are plenty of Pontiac and Oakland (no Cadillac) car models for the perfect car selfie. You may want to find the 15 quirky miniature cars decorated in a variety of styles by local artists and art groups. There are ten ’57 Chevys and three pickup trucks.


Where does historic Route 66 Start and End

It begins at Jackson Boulevard. and Michigan Avenue in downtown Chicago and ends at the Santa Monica Pier in California.

How long is Route 66

The old route runs for 2,278 miles or 3,666 kilometers from Chicago, IL to Santa Monica, CA.

What is so Special about Route 66

More than any other road in the United States, this historic trail symbolizes the renewed optimism that led to the country’s economic recovery after the Second World War.

How Long was Route 66 used

The official lifespan of this federal highway, running from east to west, was from 1926 to 1985 when it was decommissioned. 

What States Does Route 66 Go Through

The transcontinental Route 66 runs through eight different states within the United States. From east to west, it runs through Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona, and California. It is part of the interstate highways across America.

What National Parks are on or near Route 66 

Going down this route, you can visit the following National Park or Park Service (and Historic sites) on or near Route 66:

  1. Lincoln Home National Historic Site, Illinois
  2. Gateway Arch National Park, Missouri
  3. Ulysses S. Grant National Historic Site, Missouri
  4. Chaco Culture National Historical Park, New Mexico
  5. Petroglyph National Monument, New Mexico
  6. Petrified Forest National Park, Arizona
  7. Grand Canyon National Park, Arizona
  8. Hoover Dam & Lake Mead National Recreation Area, Nevada
  9. Mojave National Preserve, California
  10. Joshua Tree National Park, California

This article originally appeared on Savoteur.


Margarita is the creator and author of a travel and lifestyle blog that focuses on travel to the US, Canada, Colombia and Europe. Bringing unique insight on museums, cultural activities and luxury accommodations. She loves a good girl’s getaway and traveling with her adult children - family travel but with cocktails. Colombian by birth Canadian by nationality she here to help others organize their lives and travels.