Drive Illinois Route 66 from Chicago over a weekend or longer with this handy itinerary we followed, including top drive-ins and surprising nature stops!

Route 66, also called the “Mother Road”, is one of the most famous highways in America. Dating back to 1926, it originally st­retched from Chicago, Illinois to Santa Monica, California, connecting big cities and small rural locations. In Illinois, explore a portion of old Route 66 with some surprising historic and modern attractions, taking the time to volunteer along the road, recreate, eat, drink and learn.

This Route 66 itinerary can be done in two days or more. It starts in Chicago and includes some unlikely stops, like Midewin National Tallgrass Prairie, where bison roam. Spend a long weekend on this road trip or consider adding on our Illinois Ottawa & the Heritage Corridor Itinerary to extend this trip.

Route 66 spans eight states and three different time zones. The Illinois section of historic Route 66 stretched for 301 miles. To check out the best preserved spots today, we suggest mapping out your route prior to departure. Below are some good picks!

Polk-A-Dot Drive In in Braidwood. Darley with DebyJo Ericksen and a cool 1962 Buick Skylark Convertible.

Top Illinois Route 66 Road Trip Stops

Day 1 Chicago to Joliet

Start your adventures in Chicago and see the “Begin” Route 66 sign at E. Adams St., just west of its intersection with S. Michigan Ave. Drive about an hour south to see the Launching Pad and the Gemini Giant in Wilmington. One of the infamous fiberglass giants that was manufactured to actually look like a space man, the Gemini Giant is one of the most photographed giants that stretch across the United States.

In addition to the Gemini Giant, Wilmington, Illinois has other Route 66 attractions. Driving further past the Gemini Giant, you’ll spot on your right, the green dinosaur Sinclair on what used to be an old gas station. Head on just a bit further to intersect with Water Street, known for its antiques shops.

The Gemini Giant, a must for photos along your road trip.
The Gemini Giant, a must for photos along your road trip.

If you’re hungry or want another fun stop, drive over the bridge and on to Nelly’s Restaurant to sign your name on the wall or head further to the Polk-A-Dot Drive In, a 1950’s style diner which has tasty burgers, malts, milkshakes and fries. Located in the town of Braidwood, James Dean, Marilyn Monroe and Betty Bopp are all there to greet you at the Polka-Dot, as are the Blues Brothers- “Joliet” Jake and Elwood, and a nine foot tall Elvis. The Polka Dot Drive In in Braidwood should be on your itinerary. Stop for lunch or just a milk shake.

Drive on to Joliet. The Des Plaines River runs through Joliet, a city known as not only the site of the world’s first Dairy Queen, but also for the historic Rialto Square Theatre, an architectural masterpiece. Opened as a Vaudeville Movie Palace on May 24th, 1926, this historic theatre is still in operation. A slew of great comedians, actors, musicians and beyond have performed at this magnificent theater, including Jerry Seinfeld, Jay Leno, Kenny Rogers and past greats like Bob Hope, George Burns and Gracie Allen and The Marcs Brothers.

Darley Newman and DebyJo Ericksen driving by the Rialto Square Theatre in Joliet.
Darley Newman and DebyJo Ericksen driving by the Rialto Square Theatre in Joliet.

Next, make a stop at the “Rich & Creamy” for ice cream, just a five-minute drive from the Rialto. Grab a turtle sundae and have a seat on the bench or stroll down to an overlook, where you’ll see the Joliet Prison, made made famous by the Blues Brothers movie and television show, Prison Break.

Stay tonight in the Harrah’s in Joliet and walk over a few blocks to dine at Juliet’s, a casual, but nice Italian style restaurant with a diverse menu right downtown.

Day 2 Route 66 Bison at Midewin National Tallgrass Prairie

Start your morning in Joliet with a stop at Milano Bakery, where the DeBenedetti family have been making breads for the Chicagoland area for three generations. Their shop features strudels, pastries, homemade breads and cookies for breakfast or to have later in your day on a picnic at Midewin.

Though Illinois is nicknamed “The Prairie State,” there’s not a lot of prairie left in Illinois­–– less than 0.01% of Illinois’ original 21 million acres of prairie remains. To find out why, head to a more unusual stop along old Route 66. At Midewin National Tallgrass Prairie, experts and volunteers are working to restore the tallgrass prairie ecosystem. You can explore this beautiful ecosystem in a variety of ways.

Go horseback riding at Midewin National Tallgrass Prairie to see how tall that prairie grass really reaches!
Go horseback riding at Midewin National Tallgrass Prairie to see how tall that prairie grass really reaches!

Managed by the U.S. Forest Service, Midewin offers a variety of activities for the whole family. Enjoy walking the grounds, saddling up on a horseback ride, cycling or participating in a volunteer activity. The trails are open year round. There are also regular special events at Midewin, something to consider when planning your trip, like guided ranger hikes. Of course, a highlight at Midewin is their herd of bison, but keep in mind that it’s not always guaranteed that you’ll see them.

Flowers at Midewin National Tallgrass Prairie
Flowers at Midewin National Tallgrass Prairie

Midewin has a rich history relating to Native American tribes, bison, farmsteads and even World War II. Before it was a USFS site, it was the Joliet Army Ammunition Plant and they made munitions here during World War II. The plant operated during World War II, and also during the Korean and Vietnam Wars. Women were an important part of the wartime workforce, particularly during World War II when they, too, were packing and loading TNT. You can walk by old ammunition storage bunkers at Midewin. Rangers offer guided hikes around Midewin on various dates.

The Visitors Center here has lots of great information, so stop by to get context on Midewin before you explore on your own or join a guided tour. We went horseback riding with the Will County Trail Riders and equestrians are welcome to bring their horses to ride here, but you can also hike or enjoy cycling.

After enjoying Route 66 nature, continue on to Ottawa and Starved Rock County or keep on driving along Route 66 for more American road trip adventures.

Watch this episode “Travels with Darley: Illinois Route 66 & Midewin” on Amazon Prime.

Leave a Comment


No comments yet. Why don’t you start the discussion?

    Leave a Reply