Buckle Up! 21 Incredible Attractions Along Illinois’ Route 66

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Experience the nostalgic charm of mid-century America with a journey along the iconic Route 66, which spans 2,448 miles from downtown Chicago, Illinois, to the famed Santa Monica Pier in California. Start your adventure with the First Hundred Miles, which offers an easy and manageable drive over a few days from Chicago to Pontiac, Illinois.

Along this stretch of Route 66, you’ll encounter charming museums, quaint restaurants, historic landmarks, and even quirky attractions like the giant green spaceman. Begin your adventure with a few nights in Chicago before heading south to Joliet and concluding your journey in Pontiac.

Start in Chicago

Route 66 sign Photo Credit Heritage Corridor Destination
Route 66 sign Photo Credit: Heritage Corridor Destination

It all starts here.  There is no better way to commemorate the mother of all road trips than the Route 66 Begins sign in downtown Chicago.  Half a block from one of many museums on Route 66—the Art Institute of Chicago is a starting line for photo ops on this 2,448-mile (3,940 km) journey into nostalgia.

The journey begins at the intersection of Adams Street and Michigan Avenue in downtown Chicago, marked by the iconic Route 66 Begins sign. Situated conveniently near the freeway and just a stone’s throw away from attractions like the Art Institute of Chicago, it serves as the perfect starting point for capturing memorable photos and embarking on this epic, nostalgic adventure.

Millenium Park and Buckingham Fountain

Buckingham Fountain Chicago Photo Credit DownshiftingPRO
Buckingham Fountain Chicago Photo Credit DownshiftingPRO

In The Windy City, there’s no shortage of activities to enjoy. Start your day with a boat tour to admire the stunning architecture, or wander down the Magnificent Mile for some retail therapy. For a cultural experience, don’t miss the chance to visit the Art Institute of Chicago and immerse yourself in iconic art.

Alternatively, explore Millennium Park, conveniently located next to the Art Institute. Snap a selfie by ‘The Bean’ or marvel at the dynamic faces of the fountains. Wander through the park’s lush gardens and make a pit stop at Buckingham Fountain, recognizable from the opening credits of ‘Married with Children’ if you’re feeling nostalgic.

The Bean (Cloud Gate)

The Bean in Chicago Photo Credit Alpegor6 via Depositphotos 1
The Bean in Chicago Photo Credit Alpegor6 via Depositphotos

No visit to Chicago would be complete without a visit to “The Bean.” Located in Millennium Park in Chicago, “The Bean,” formally known as Cloud Gate, is a captivating stainless steel sculpture designed by artist Anish Kapoor. Its reflective surface offers a unique perspective of the city skyline, drawing visitors to admire their distorted reflections and the surrounding architecture. A symbol of modern art and urban innovation, experiencing The Bean is essential for anyone exploring the vibrant culture of Chicago.

Art Institute of Chicago

Seurat at AIC Photo Credit DownshiftingPRO 1
Seurat at AIC Photo Credit DownshiftingPRO

One of America’s most important art museums, the Art Institute of Chicago, invites exploration. Don’t miss the chance to explore Grant Wood’s iconic “American Gothic,” a captivating portrayal of rural Americana that has become a symbol of its identity.

At the Art Institute of Chicago, you’ll find Seurat’s renowned masterpiece, “A Sunday Afternoon on the Island of La Grande Jatte.” This iconic painting is celebrated for its meticulous pointillist technique and depicts a leisurely scene along the Seine River.

Museum Campus

Field Museum in Chicago Photo Credit bloodua via Depositphotos 1
Field Museum in Chicago Photo Credit bloodua via Depositphotos

Nestled by the calm waters of Lake Michigan, Chicago’s Museum Campus is a hub of discovery and learning. Here, you’ll find three awesome museums: the Adler Planetarium, the Shedd Aquarium, and the Field Museum. It’s like a treasure trove of knowledge right by the lake!

You can gaze at stars and planets in the Adler Planetarium, dive into underwater worlds at the Shedd Aquarium, and explore ancient dinosaurs at the Field Museum. And while you’re learning cool stuff, you can enjoy the beautiful views of the lake right nearby. It’s a perfect spot for a day of fun and discovery!

Burr Bridge, IL Route 66 Shield

Burr BridgeIL Route 66 sign Photo Credit DownshiftingPRO
Burr BridgeIL Route 66 sign Photo Credit DownshiftingPRO

Heritage Corridor purchased and installed 12 interactive monuments along Route 66. The monuments are located in Joliet, Burr Ridge, Willowbrook, Romeoville, Lockport, Gardner, Dwight, Pontiac and Bolingbrook. Additional monuments are coming soon in Darien, Oak Brook Terrace, Wilmington, Elwood, Chicago Southland Oasis, and Crest, another Joliet location.

Harvester Park

Harvester Park Photo Credit DownshiftingPRO
Harvester Park Route 66 Photo Credit: DownshiftingPRO

Harvester Park provides a unique family outing, designed as a tribute to Route 66. The park features playful recreations of iconic roadside attractions from all eight states along the historic road, such as a slide resembling the Willis Tower and the famous Blue Whale. Situated near the original Route 66 path, the park offers both Route 66 enthusiasts and children a fun and educational experience, with custom-made landmarks and opportunities to learn about the route’s geography and attractions.

Joliet IL Route 66 Shield

Joliet IL Route 66 sign Photo Credit DownshiftingPRO
Joliet IL Route 66 sign Photo Credit DownshiftingPRO

This is the perfect opportunity to take a picture to commemorate your drive through the First 100 Miles from Chicago to Pontiac, IL. The Route 66 shield is located in downtown Joliet at the Historical Museum and Welcome Center.

Joliet Area Historical Museum and The First 100 Miles Welcome Center

Joliet Area Historical Museum Photo Credit DownshiftingPRO 20230926 130030 0017
Joliet Area Historical Museum Photo Credit DownshiftingPRO

Nestled within the Joliet Area Historical Museum, The First Hundred Miles Welcome Center offers an array of Route 66 memorabilia alongside unique gifts crafted by Illinois Makers. As you explore the museum’s lobby, don’t miss the chance to glimpse two iconic Blues Brothers suits worn in movies. Additionally, an exhibit detailing the construction of the Michigan-Illinois Canal adds a fascinating historical dimension to your visit.

Rialto Theater

Rialto Theatre in Pontiac Photo Credit Heritage Corridor 20230926 130029 0003
Rialto Theatre in Pontiac 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 to be one of the most beautiful theatres in the nation, the marquee will be what you want to se—and commemorate.  Shiny and bright, it lights up at night!

Joliet Route 66 Diner

Route 66 Diner Joliet Photo Credit DownshiftingPRO 20230926 130030 0008
Route 66 Diner Joliet Photo Credit: DownshiftingPRO

Entering this establishment, prepare to be whisked back to the charm of a traditional diner. Indulge in bottomless cups of coffee and hearty biscuits and gravy while taking in the nostalgic decor and vintage wall signs reminiscent of the 1950s and 60s. Highly recommended for a fun and nostalgic dining experience.

Illinois Rock & Roll Museum on Route 66

Illinois Rock and Rold Museum on Route 66 Photo Credit DownshiftingPRO 20230926 130030 0013
Illinois Rock and Rold Museum on Route 66 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. 

Old Joliet Prison

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Made famous by The Blue’s Brother’s movie stop at The Joliet Prison. The walking tour delves into the prison’s history from its establishment in 1858 to today, offering insight into its significant role in Joliet’s history. As a popular stop along Route 66, the Old Joliet Prison is both intriguing and somewhat eerie, drawing visitors worldwide. While parts of the tour may not meet ADA standards due to the site’s age and condition (let staff know so accommodations can be made).

The Gemini Giant

Gemini Giant Photo Credit DownshiftingPRO 1600x900
Gemini Giant Photo Credit DownshiftingPRO

The Launching Pad Drive-In (now 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 on
Route 66. Since 1965, he’s been watching travelers with his bright green suit and silver rocket in hand. Great photo-op!

Polk-a-Dot Drive-in

Polk A Dot Diner on Historic Route 66 Photo Credit DownshiftingPRO
Polk-a-Dot 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 sign to the retro interior and selfie-worthy pop culture statues
outside, you’ll feel like you’ve traveled back in time.

Dwight, IL Route 66 Shield

Dwight IL Route 66 sign Photo Credit DownshiftingPRO
Dwight IL Route 66 sign Photo Credit DownshiftingPRO

A perfect place to have a picnic at the Dwight Route 66 shield. There is a picnic table and a a play area within walking distance to the Ambler-Becker Texaco Station.

Ambler-Becker Texaco Station

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Ambler-Becker Texaco Station – Dwight, IL Photo Credit: DownshiftingPRO

This historic 1933 filling station was the longest-operating gas station along Route 66. Now, it serves as Dwight’s Welcome Center along Route 66. 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 a Route 66 shield and an old-style billboard for the perfect Instrammable op.

Route 66 Association of Illinois Hall of Fame and Museum

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Route 66 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 Street Photo Credit DownshiftingPRO 20230926 130030 0016
Murals on Main Street Photo Credit DownshiftingPRO

Downtown Pontiac, IL.  A collection of 19 outdoor murals around the historic downtown was created in four days during the Walldog Summer Bash 2009.  These vignettes will remind you of a Norman Rockwell version of America in the 20th century. Plenty of opportunities to pose with these murals to blend in with the story!

Pontiac-Oakland Auto Museum

Pontiac Oakland Auto Museum Photo Credit DownshiftingPRO 20230926 130030 0012
Pontiac Oakland Auto Museum Photo Credit: DownshiftingPRO

The museum offers a fascinating glimpse into the past, from classic Pontiac and Oakland car models showcasing the evolution of design and engineering to meticulously restored vehicles that embody the spirit of American craftsmanship. Each exhibit tells a story, inviting guests to immerse themselves in the rich heritage of these iconic automotive brands. With its curated collection of vintage cars, memorabilia, and interactive displays, the Pontiac-Oakland Auto Museum promises an unforgettable experience for enthusiasts and casual visitors alike.

Find the Minature Cars

Miniatures in Pontiac Photo Credit DownshiftingPRO 1
Miniatures in Pontiac Photo Credit DownshiftingPRO

A wide array of Pontiac and Oakland car models provides excellent options for capturing the perfect car selfie. However, for a more unique experience, consider exploring a collection of 15 miniature cars adorned with various artistic styles by local artists and art groups. This collection includes ten miniature ’57 Chevys and three meticulously decorated pickup trucks.

More Road Trip Suggestions

Road Trip Photo Credit Get ArturVerkhovetskiy Depositphotos 1
Road Trip Photo Credit Get ArturVerkhovetskiy Depositphotos
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Margarita Ibbott is a travel and lifestyle blogger. She blogs about travel in Canada, the United States and Europe giving practical advice through restaurant, hotel and attraction reviews. She writes for DownshiftingPRO.com and other online media outlets.