Route 66 in Illinois: Cruising a Legendary Highway

While most routes are meant to get you directly to a destination, Route 66 in Illinois is all about the journey.

Hit the open road and explore charming small towns, historic sites, kitschy attractions, popular diners and more. Here’s a handy checklist for cruising Illinois’ Route 66. What are you waiting for?

Chicago: The Ultimate Road Trip Begins Here

Start your journey at the historic Route 66 marker on East Adams Street between Wabash and Michigan avenues. From here, it’s a close walk to The Art Institute of Chicago, Millennium Park and shopping on The Magnificent Mile. Marvel at the exhilarating views from the 103rd floor of Willis Tower at Skydeck Chicago. Visit the Cloud Gate sculpture (also known as “The Bean”) at Millennium Park. Eat at Lou Mitchell’s, where patrons are treated to complimentary donut holes. A Chicago institution, Lou Mitchell’s has served up irresistible diner fare to presidents, governors, athletes and celebrities. Join this illustrious group, and fuel up with a hearty breakfast or lunch before hopping into your rental car and hitting the road.

Joliet: Architecture and Americana

Tour the opulent Rialto Square Theatre, built in 1926 and originally a vaudeville movie palace. The four-story, Neo-Baroque-style structure is now a thriving musical, play and concert venue. Rumor has it that it’s haunted by the ghosts of former performers (it was once featured on SyFy’s “Ghost Hunters” TV series). Another of the city’s architectural landmarks is the Old Joliet Prison. As you enter the grounds, you’ll be struck by the imposing structure and amusing signage, “Get Locked Up…At the Old Joliet Prison.” The prison’s storied past includes being a film location for the movie, “The Blues Brothers” and the popular TV series, “Prison Break.” Plan a stop at the Route 66 Welcome Center, where you can kick back in a classic car, walk the Route 66 map and sip a bottle of Route 66 soda.

Pontiac: Automobiles, Murals and More

Car buffs won’t want to miss the Pontiac-Oakland Automobile Museum, housing a substantial collection of Pontiac and Oakland brand vintage cars. Head to the Route 66 Association Hall of Fame & Museum to discover playful facts and stories about the Mother Road. You can’t come to Pontiac without admiring the Murals on Main Street. Just follow the red-painted footprints on the downtown sidewalks for a fun-filled, self-guided tour. Top off your stay with a trip to the ever-popular Edinger’s Filling Station, a 50s-style diner specializing in comfort food like savory chicken pot pie and deliciously gooey macaroni and cheese.

Springfield: Retro Diners and Drive-Ins

Motor into Springfield, the capital of Illinois that’s well known for its status as the long-time home of revered president Abraham Lincoln and its quintessential Route 66 diners. Cozy Dog Drive In has garnered a loyal following with their eponymous hot dog on a stick, made with top secret batter and promptly fried since 1946. If you’re in the mood for spice, drop by The Chili Parlor for a bowl of rich and savory chili. Open since 1945, the diner was once featured on the Travel Channel’s “Food Paradise.” Plan your trip for September to attend the International Route 66 Mother Road Festival, a celebration filled with classic cars, Route 66 memorabilia and wonderful festival food and vendors in the heart of town. Before you leave, experience the novelty of cinema under the stars at the Route 66 Drive-In movie theater.

Edwardsville and Glen Carbon: Explore, Eat and Antique

On your way to Edwardsville, make a stop in Livingston to hunt for antiques and gifts at the Pink Elephant Antique Mall. Then, venture down memory lane at the Wildey Theatre on Main Street Edwardsville. A historic landmark, this stately theater features live performances and shows classic films. This is the third oldest city in Illinois, so you’ll want to wander through the Downtown Historic District and check out the architecture. In the surrounding neighborhoods, check out homes built circa 1890 through 1930 in the Leclaire and St. Louis Street National Historic Districts, as well as the Brick Street Landmark District.  If you’re hungry, a custom-cut steak dinner awaits you at the 1818 Chophouse, or opt for lush frozen delights at Annie’s Frozen Custard.