Route 66 is one of the most iconic highways in the world. Known across the world, this historic stretch isn’t just an excuse to cruise through the Midwest, but also one of the best ways to see all that Illinois has to offer. The road runs through the heart of the state, uniting historic landmarks and spellbinding cities alike.
So get your playlist ready, the roof off your car, and pump that gas as we prepare the road trip of a lifetime. It’s time to see Illinois through Route 66.
Route 66 start: Chicago
When you’re kicking off your Route 66 experience in the Windy City, you know you’re in for a real adventure. Located near the start line, The Buckingham Fountain is definitely worth a visit. While the water shows occur every hour on the hour, at dusk is when it really shines. These light shows are spectacular – beaming until the last one at 10.35pm.
Once you’ve taken your selfies, it’s time to experience the city. Not only is Chicago a sight to behold – from its glorious skyline to absolutely electric atmosphere – it also contains two of the most iconic gay districts in the country.
Boystown is a must-visit. Delicious food and wonderful shops aplenty, but the main hub is the bar scene on Halsted Street. Meanwhile, Andersonville is much more chilled, catering to a large lesbian population and delivering a unique hub of arts and food. Check out our full guide on the two districts to really get the most out of it.
Next stop: 30 miles to Joliet
Now the road trip really begins. Before setting off, make sure you grab breakfast at Lou Mitchell’s, a traditional diner and Chicago landmark that serves over 1000 people daily.
Then it’s time to fire up the aux and make a short trip down the route, before finding yourself in Joliet. Cinema lovers should head to the Rialto Square Theatre. The spectacular design makes the historic sight something to behold. Alongside the aesthetics, movies, singalongs and musicals can all be found within the walls.
The gay scene might be lagging behind the juggernaut of Chicago, but you can still head to the much-beloved Maneuvers Gay Bar. Expect drag shows, a welcoming environment, and a bar that’s open till late every day of the week.
Next stop: 60 miles to Pontiac
Step back in time before you move on at the Polk-a-Dot Drive in, where rock-n-roll, 50s and 60s memorabilia, and classic diner food are served in equal measure. Then once you reach Pontiac, there are two more stops you can make.
Motorheads can hop into the Pontiac Oakland Automobile Museum. The famous site treats guests to displays of car models from the early 1900s to now. Or, for extra throwback fun, head to the Route 66 Hall of Fame and Museum to get a full history lesson on the iconic stretch of road. Then as you leave, your Instagram will probably enjoy a few photos at the Murals on Main Street.
Next stop: 106 miles to Springfield
The capital of Illinois is a must-visit, and luckily Route 66 goes straight through it. The birthplace of Abraham Lincoln, the whole town is a monument to one of the country’s most beloved Presidents. If you want the full experience, head to Abraham Lincoln Presidential Library & Museum, featuring lifelike replicas of him, his family, and key players in his life. Check out our full guide of what to do in Springfield for the best tips.
As for the gay scene, Springfield has one main bar and club: Club Station House. Open till 3am every day except Sunday, it combines a community vibe with amazing shows to create one of the more unique experiences in the city.
Final stop: 91 miles to Chain of Rocks Bridge
On the final stretch, you have to stop off to eat at the Cozy Dog Drive In. This is where the first ever corndog on a stick was created, which is now such a staple of American culture that it ranks up there with baseball.
While we’re on whacky landmarks that could only be found in Illinois, you’ll need to stop off at Henry’s Rabbit Ranch. Created by an eccentric local, this is exactly what you think it is: a ranch filled with endless bunnies. If that’s not an iconic queer location, we don’t know what is.
Fans of true crime might want to make a stop at Luna Cafe. Not only does its retro aesthetics and vintage sign make it a must-visit place, but crime lord Al Capone used to love the place.
Finally, you reach the end of the road: the Chain of Rocks Bridge. The world’s longest bicycle and pedestrian bridge also heads off into Missouri. Now, park up your car and enjoy the view, because you’ve just seen the best in Illinois via Route 66.
Illinois Office of Tourism is a partner of Gay Star News