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Route 66 Route Trip Day 1: Chicago to Springfield

Follow along on our Route 66 Road Trip turn-by-turn along the Mother Road from Chicago to Los Angeles! Day 1 from Chicago to Springfield included breakfast at Lou Mitchell’s, two looming muffler men, a larger-than-life Lincoln in the World’s Largest Covered Wagon, and lots of vintage signs! 

Route 66 Route Trip Day 1: Chicago to Springfield

We spent one day in Chicago exploring the city before embarking on our Route 66 road trip and you can read about our day in Chicago here. I don’t think one day is enough time to truly explore the city, but we did our fair share including Lou Malnati’s pizza, the Bean, the Art Institute of Chicago, a Chicago-style hot dog, and random walks around the city. What we missed: Willis Tower, Billy Goat Tavern, Wrigley Field, Wicker Park, an architectural cruise, and the beach.

If we were simply visiting Chicago, I would have given us more than a day to explore, but since we were embarking on an 18-day Route 66 Road Trip, a day was all that I allocated. 

The next morning, we started off the road trip with a good breakfast at Lou Mitchell’s. If you are doing a Route 66 trip, start it or end it at Lou Mitchell’s! The food was excellent! And when they seat you at a table, everyone gets a donut hole and the ladies and kids get Milk Duds!

We then drove to the Route 66 start sign to snap the obligatory photo. Yup, there’s the husband and the Volvo at the start!


And then we were off!

Our first stop was Henry’s Drive-In with it’s hot dog sign in Cicero, outside of Chicago. And across the street was the awesome Robin Hood Mufflers sign.

Then we came across our first muffler man: the Launching Pad’s Gemini Giant.

The Launching Pad went out of business, but luckily it’s muffler man is still there. While photographing and sketching the Gemini Giant, we encountered our very first “character” of the Route 66 road trip. Two men pulled up in a car. The driver got out and introduced himself to us as “Sticks.” Or maybe Stix, I’m really not sure. He told us that he is a bookie, that he used to work construction, but he had an accident, and is now on disability. The guys that he used to work with now place bets with him and he “gambles hundreds of dollars.” This was all unprompted. They snapped a photo and then drove away.

We then drove by some of the first billboard advertising ever made! Meramac Caverns would advertise on the sides of barns and there are several in this first stretch along Route 66!

Next up was Tall Paul in Atlanta, Illinois holding a hot dog. He was pretty cool. He had been moved to his new location in order to “preserve” him when his former residence was sold.

We then rolled through Lincoln, Illinois. They seriously like their Abe Lincoln there. We stopped at the World’s Largest Covered Wagon which is manned by a large, law-reading Mr. Lincoln. Yes, the world has a largest covered wagon, and steering it is Abraham Lincoln.

 The town also has a serious Lincoln mural collection. I was yelled at by a man who rolled out of a bar after I was taking some mural and wall photos. I was almost back to the car when he started yelling, “Hey, Hey! Whatchu takin’ pitchers fer?” I shit you not. He said it like that. When I didn’t answer, he whipped out his flip phone and started taking photos of us.

My husband wanted to explain to him that I was taking “art photos,” but I told him to forget it, that the man was clearly drunk and crazy and I didn’t want to deal with it.

There was also an awesome vintage neon sign somewhere near Lincoln for The Tropics which was, unfortunately, shut down.

We then rolled into Springfield which was our stop for the night. We stayed at the State House Inn which had been recently remodeled in a Mid-Century Modern Mad Men style. It was clean and affordable, so I definitely recommend it, but be sure to check out any current reviews.

Stay: State House Inn, 101 E Adams St, Springfield, IL 62701.  (217) 528-5100

Planning your own Route 66 Road Trip? I used the Route 66: EZ66 Guide for Travelers to plan our trip and I highly, highly, highly (I truly cannot emphasize it enough) recommend the book/maps if you’re planning to drive most of Route 66 turn-by-turn – meaning all of the historic route, no modern-day highways.

Follow along on the rest of our Route 66 Road Trip:

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Monday 7th of August 2017

How many hours driving was your Day 1 route ? I'm currently planning my route, day by day, (I'm allowing for 3 weeks for the entire trip). However, I feel it is a long drive from Chicago to Springfield in 1 day. Any suggestions....


Monday 7th of August 2017

Hi Ciaran, I honestly don't remember the actual hours since it's been a few years now, but I can tell you that my husband and I are NOT early risers, we probably had breakfast at Lou Mitchell's around 10:30/11 am and then hit the road. When we stopped at the muffler men and the giant Abe Lincoln, my husband actually stood and sketched them (I quickly photographed them, but he stood there and drew them for 10-15 minutes each), and we still arrived in Springfield before sunset. For me, there was nothing else I really wanted to see or spend time at along that portion of the route, so a day 1 Chicago to Springfield made sense for us and we didn't feel rushed at all. Hope that helps!


Wednesday 9th of July 2014

LOVE Lou Mitchell's! My office is across the street so we stop in pretty regularly. Great call! Hope you enjoyed the city...

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