10 Route 66 Attractions to See in Illinois

Photographing the iconic Begin Route 66 and First Route 66 signs in downtown Chicago is a must-do for every “Mother Road” enthusiast. Even though the starting point of the Route has moved a lot over the years, the sign found on E. Adams Street is the current and technical starting point in Illinois. 

The First Route sign, also known as the End Route sign, sits on Jackson Boulevard near Michigan Avenue and marks the original beginning of Route 66 and its current terminus. Before you continue your journey, check out the amazing neighborhood with The Art Institute of Chicago, great parks, and cool monuments. Then, grab a coffee and sandwich at a nearby café and you’re ready to go. 

Built in 1858 and in operation until 2002, Old Joliet Prison is now a historic site where you can learn about life in a penitentiary along the Route 66. You can explore Old Joliet on self-guided daytime or twilight tours and informational signs will guide you through the buildings’ history. The guided “After Dark” tours at dusk cover the grim side of this historical prison. All tours take about 1–1.5 hours and an advance booking is required. 

You might recognize Old Joliet from the Blues Brothers movie or the Prison Break TV series. Occasionally, there are events around the Blues Brothers theme, so you might bump into Jim Belushi himself on your visit. 

Route 66 Association of Illinois hosts the Route 66 Hall of Fame and Museum which is packed full of memorabilia associated with the history of Route 66. This classic museum boasts the bus and van of Route 66 legend Bob Waldmire, merchandise, photographs, and even the odd landmark plucked from the Route. For a cool photo, check out the world’s largest Route 66 shield mural and other wall decorations. 

Each year in June, the Association organizes a Motor Tour that provides you an opportunity to drive and appreciate attractions along the Illinois stretch of Route 66 as a group. They alternate between a south start every odd year and a north start every even year. 

If classic cars are your thing, then put the pedal to the metal and make your way to Pontiac Oakland Auto Museum. This fun museum hosts one of the greatest collections of old and new cars, dealer items, literature, and generally all things related to the Oakland and Pontiac automobile brands. 

As the museum frequently rotates the featured cars and displays, you’ll always discover something new. They take immense pride in presenting a pair of nearly identical cars so that you can make comparisons and examine all the finer details of these amazing automobiles. You’ll also find fully restored 1969 and 1970 GTO Judges on display, highlighting how years’ worth of TLC brings these great cars back to life. 

Ambler's Texaco Gas Station in Dwight is said to be the longest-operating gas station along Route 66, dispensing fuel from 1933 until 1999. It’s been restored to its former glory and serves as Dwight’s visitor center. It features classic gas pumps, a Texaco sign, and a vintage fire engine in the service bay. The station’s cottage look stems from when oil companies were introducing gas stations to suburban America and wanted to give them a homey and inviting style.  

A couple of minutes' drive away, you’ll find Dwight Banking Center, designed by Architect Frank Lloyd Wright in 1905, and the C&A Railroad Depot, built in 1891. Dwight Lions Lake Park makes for a pleasant stop on your journey. 

To sample a real piece of Route 66 history in Illinois and enjoy an original hot dog on a stick, pull up at the historic Cozy Dog Drive-In in Springfield. Opened in 1949, the Cozy Dog Drive-In is a low-key, memorabilia-laden, counter-serve diner famous for its corn dogs and burgers. It’s said to be the home of the hot dog on a stick, dipped in batter, deep fried, and ever so delicious. 

Breakfast is served until 11 am, so you can fuel up on eggs, toast, pancakes, or hash browns before hopping behind the wheel. The lunch and dinner menu includes the famous cozy dogs, cheese sandwiches, burgers with fries, onion rings, potato salad, and much more. 

Versatile Springfield with its extensive Abraham Lincoln legacy is a must-stop on every history buff’s itinerary. President Lincoln lived in Springfield from 1844 to 1861, and his downtown home has been perfectly restored and opened to the public. 

Springfield is also the final resting place for President Lincoln, his wife Mary, and 3 of their sons. To honor the Lincoln family, book a tour of the interior space of the Lincoln Tomb. In the Abraham Lincoln Presidential Library & Museum, you’ll step inside key moments in Lincoln's life with interactive displays and unique artifacts. Before you leave the city, check out the Illinois State Capitol which is the largest non-skyscraper capitol in the US, standing at 361 ft.  

Roll down the window, turn up the volume, and take in the nostalgia as you cruise down the original historic Route 66 brick road in Auburn. Stop for a perfect road trip photo of this beautiful, 1.4-mile-long stretch of restored, hand-laid brick road. 

Listed on the National Register of Historic Places, this segment of Route 66 began as Illinois 4, serving as US 66 from 1926-1930. Later, it was improved by widening the roadway and removing the 90-degree turns, mostly by bypassing them. At this time, a brick surface was added to the route along Snell and Curran Roads. You’ll find the road about 2 miles north of Auburn, surrounded by the lush Illinois countryside landscape. 

The Cahokia Mounds State Historic Site is one of the largest archaeological sites north of Mexico, built by the Mississippian civilization between 600 and 1400 AD. The site includes over 80 mounds and if you climb to the top of the largest one, Monks Mound, you’ll be rewarded with a stunning view of the surrounding area. This UNESCO World Heritage Site is home to the Cahokia Mounds Museum, which features exhibits on the history and archaeology of the site and this mysterious civilization. 

Located along the Mississippi River, the site offers hiking trails, picnic areas, and anything else you’d need for a great day of exploration and discovery. Collinsville also boasts a 170-ft water tower disguised as a ketchup bottle. 

What better way to end a road trip on Route 66 than taking a stroll on the Old Chain of Rocks Bridge and admiring the spectacular scenery? This beautiful bridge, opened in 1929, spans the mighty Mississippi River and is the end point of the Illinois Route 66 with its eastern end on Chouteau Island, Illinois, while the western end is on the Missouri shoreline. 

The bridge is only 1 mile long and 24 ft wide. It towers more than 60 ft above the water and features a unique 30-degree turn midway across the river. It’s currently open daily for pedestrians and cyclists and the perfect spot to stretch your legs after a long drive to the finish line.