1. Polka-a-Dot Drive In in Braidwood
The history behind this restaurant is pretty unique, as Enjoy Illinois states the original eatery was a former school bus the owner, Chester “Chet” Fife, converted into a restaurant. Chet used this bus to serve delicious and classic American foods, such as burgers, fries, milkshakes, malts and more from 1956 to 1962, where the current building stands today.
Taking a step into the diner is like taking a step back in time, as the building is filled with jukeboxes and fun artifacts from the 50s. Even the parking lot represents that time period, as statues of James Dean, Elvis Presley, and Marilyn Monore stand tall over the parked cars.
How much I want to visit: 7.8/10
Although it was probably more practical to move to a building rather than stay on a bus, I can’t help but think about how cool it would have been to see the original bus. How on earth did Chet manage to use it to cook food for six years? Also, I’m kind of loving the idea of Chet driving the bus around, making it into a mobile restaurant. Okay, that may not have worked back then, but it’s fun to think about!
2. Doc’s Soda Fountain in Girard
Everyone has a sweet tooth and stopping at this adorable soda fountain looks to be the perfect fix. Although the business has been serving up some sweet treats since 1929, it was originally a chemist store back in 1884. Doc’s didn’t forget its roots though, as both Coca-Cola relics and a display of old school pharmacy supplies can be seen on display. Combine that with the mouth-watering menu full of ice cream, chocolates, cookies, sodas, and other sugary goodness, and this stop makes for one heck of a good time,
How much I want to visit: 8.3/10
While I love everything chocolate and ice cream (my favorite flavor is mint chocolate chip, I said it and I stand by it), I’m really fascinated by the old pharmacy supplies and Coca-Cola products. I love how the modern store pays tribute to its history, and I imagine it would be like traveling back to the good old days.
Also, now I really want ice cream.
3. Lou Mitchell’s – Chicago
Why not eat a bite to eat before hitting the road? Located a few blocks from the start of Route 66, this classic restaurant has been nicknamed “the first stop on the Mother Road.” The menu is literally the best of the best, with delicious pancakes, waffles, omelets, salads, sandwiches, and desserts to choose from. There’s even a sign claiming them to have “the world’s finest coffee” (cue the coffee scene from Elf), adding to the all-American experience.
How much I want to visit: 8.8/10
Imagine this: grabbing a bite to eat at Lou Mitchell’s, then heading over to see (one of the three) signs that marks the start of Route 66. Add in grabbing some of the world’s finest coffee, and that honestly sounds like the best day ever. This restaurant looks to be tucked into the busy streets of Chicago, so blink and you might miss it! Plus, who wouldn’t want to spend a day in Chi town?
4. Old Log Cabin – Pontiac
The Old Log Cabin and Route 66 have the same birth year! Also built in 1926, this quaint diner has a classic menu of eggs, burgers, fries, and shakes for tourists of all ages to enjoy.
Also, there’s some fun history behind this restaurant- the building orginialy faced Route 4, which would later evolve into Route 66. However, as the years went on, Route 66 shifted and was repositioned on the other side of the building. Not wanting to lose customers (because they couldn’t even access the door to enter!), the owners physically lifeted and rotated the structure using a unit of horses to face the new Route 66. Talk about dedication!
How much I want to visit: 9/10.
Okay, if those owners were willing to go to all that effort to move the building just to maintain business, they deserve a huge round of applause. I bet others in their position would have simply cut their losses, and abandoned the business. Add in the delicious menu with the rustic beauty of the log cabin, and this place makes for the perfect pit-stop for a yummy, home-cooked meal.
The Twistee Treat Diner and the Pink Elephant Antique Mall – Livingston
Located towards the end of the Illinois Route 66 portion, this iconic diner greets visitors with the large pink elephant statue out front to commemorate the adjoining Pink Elephant Antique Mall. Add in the ice cream cone-shaped building and the waitstaff looking as though they just came from the 50s, and this diner is the perfect final stop in Illinois before heading to Missouri. The beautiful pink and tear interior is a great throwback to the 50s, even though the building was built in modern times. Nothing sounds better than enjoying a delicious burger and milkshake, then taking a quick stroll through the antique store before continuing along Route 66.
How much I want to visit- 100/10.
Okay honestly, shame to me. I’ve driven past this diner multiple times but was always in a hurry to get to my destination. But, I promise, next time I drive past this incredible building, you can bet your bottom dollar I’m stopping for a milkshake! I love the idea of the owners paying tribute to the 50s by giving the inside decorations those vibes. Especially because looking at the outside, I would never have guessed that’s what the inside looks like! Plus, I love antique malls! Maybe I’ll find some Route 66 memorabilia?
Also, I really want to see that pink elephant in person!
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