Our Route 66 Adventure Through Illinois

Back in March, we visited the state capital of Illinois, Springfield, and one of our stops was the Illinois State Fairgrounds, where one of the Route 66 markers is located. After taking pictures and reading the information about this historic highway, along with the map highlighting the Illinois portion of the route, we thought it would be fun to drive the more than 300 miles ourselves and visit the different towns and cities along the way.

According to Wikipedia:

“U.S. Route 66 or U.S. Highway 66 (US 66 or Route 66) was one of the original highways in the United States Numbered Highway System. Established on November 11, 1926, with signage erected the following year, the highway ran from Chicago, Illinois, through Missouri, Kansas, Oklahoma, Texas, New Mexico, and Arizona before terminating in Santa Monica, California, covering 2,448 miles (3,940 km). US 66 became a major route for westward migration, particularly during the Dust Bowl of the 1930s, and contributed to the economic development of communities along its path. It later faced decline as traffic was diverted to the Interstate Highway System in the mid-20th century.”1

So, what better way to celebrate the 250th anniversary of the United States Declaration of Independence, and my 53rd birthday, than by driving Route 66? That’s exactly what we did. We built a simple plan and used ChatGPT to generate a three-day itinerary. Here’s what it looked like.

Created by Ed Ortiz using ChatGPT

Of course, the itinerary was flexible. We added several more towns along the way and even included St. Louis, Missouri, as our final stop.

We decided to stay in Chicago on Thursday night so we could begin our journey early Friday morning by walking to the traditional starting point of Route 66 at 122 S. Michigan Avenue. I later discovered that, in celebration of the upcoming 100th anniversary of Route 66, Navy Pier has also been officially recognized as a starting point. That was fine with us—we took pictures at both locations.

In total, we visited 23 cities and towns in three days, and we had a wonderful time—especially collecting stamps from the different destinations in our Route 66 passport book. Here are some of the highlights.

There is a saying in the Army: “Home is where the Army sends us.” Well, I’m not in the Army anymore, and Illinois is home now. We had a wonderful time driving through the “Land of Lincoln” and learning more about our home state. We’re already talking about driving the rest of Route 66 all the way to Santa Monica, California. God willing, we’ll make that journey one day.

  1. https://en.wikipedia.org/wiki/U.S._Route_66 ↩︎

141 thoughts on “Our Route 66 Adventure Through Illinois”

  7. What a beautiful post, Ed! Sorry I am so late to the party to see/read it! I do hope you had a great birthday, and by now, look back on it with fondness. i love your photos and how the gallery came together in a lovely quilt-type way. I have also taken a drive through Illinois, while working in Missouri for about 18 months several years ago (2002 I think it was). Amazing country and flat, as I recall. I remember route 66 being iconic, though I didn’t know there were so many special spots as Chat noted for you. Bravo in using that tool to your advantage! Happy 250th birthday to America too!

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    1. Thank you so much, Sheila. 🙏🏼 It was a great experience, and hopefully we’ll be able to complete the entire route in the near future. I know, ChatGPT did an awesome job putting together an itinerary for us!

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  8. What a wonderful trip to take! Thank you for sharing with us. How much fun and enjoyment to share this trip with loved ones. There’s nothing like seeing a part of history for yourselves.

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    1. Absolutely! Fully aware of the Green Book. A really sad part of our country’s history. I recently watched the movie, and they did a great job depicting the hardships African Americans faced back then. I have driven most of US61 and US1 up to Maryland. I bet the portion from Maryland to Maine is nice. Thank you for reading and commenting.

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  10. What a fun birthday trip, Edward. I love the idea of having a scenic road trip with a theme. I’ve been on mostly western portions of the route—it gets pretty funky in spots! Another fun and out of the ordinary road trip is the Hwy 50–Loneliest Road in America. I lived on this route in central Nevada and visitors came from all over the world to experience it. I worked at the library in Austin, NV and many travelers stopped in to visit along the way…from France, England, Norway… you name it. Thanks for all the great photos of your fun journey!

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    1. Thank you, Lori. I drove a portion of that route when I was living in Kansas, and it’s really something. You are right, there are a lot of travelers visiting these routes. We met people from Belgium at one of our stops. It’s super interesting, and there is so much history along those routes.

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    1. Thank you, Linda. It was a great trip and the weather was nice. The “Mother Road” reference comes from The Grapes of Wrath by John Steinbeck. Many people used that road to escape the severe dust storms, called the Dust Bowl, that impacted many Americans in the 1930s.

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  16. This is awesome. What a great idea to spend the weekend, and the photos are great. Your picture with the Blues Brothers is the best thing I’ve seen all week. For me, this is the kind of thing that keeps me coming back to the internet. Thanks for sharing this with us, Edward! I hope you decide to keep going so there’s more to come!

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  17. How fun!! 🤩 Always wanted to road trip Rt 66! Awesome pics – my faves are Blues Bros & that shot of your wife (I’m assuming lol) by the arch is super cool! Thanks for sharing, & happy belated birthday!! 🎉

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  18. Does your wife know about your relationship with Betty Boop? Looks like a fun and instructive journey on all counts. Thanks for the pictures, too, Edward.

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  19. Love this post! I lived in Edwardsville for a while…and in St. Louis…so fun to see pics of places I remember on the “scenic path” to get from Chicago to Southern Illinois. Twenty-three cities in just a few days? Road warriors! Thanks for taking us along. 💝💝💝

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  20. Edward, what a fabulous post! I *loved* the photo gallery. Also, belated wishes for a wonderful birthday. We must almost be “birthday siblings.” I used to wish to do a big RV trip all the way across Route 66. I have a 3/4ths finished urban fantasy novel that is basically set on the “Mother Road” (but in 1970). Oh, the fun I had doing research! I built my own magical mythology about the highway. Although I never did decide on a satisfying way to dispose of the super-villain… my ending didn’t work for me. I registered the copyright, but never published it. Here’s a trailer I made about it, when I was gearing up to publish. Just sharing an infatuation for the Mother Road. Have a splendid weekend — and celebrate your birthday all month. Hugs.

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  23. This looks like a wildly fun time! I love the giant hot dog man, and the photo of the famous arch. Did you go up? I was so surprised at those ancient elevators and how cramped it is at the top. I thought, for some reason, it would be more like the Empire state building.

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    1. Thank you, Bridgette. It was a fun trip. We didn’t go up this time, but we did back in 2009. Yeah, their system is definitely weird and we were surprised, but it was great once we were at the top looking out through the windows.

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  24. What a fun trip – thanks for bringing us along! I always enjoy reading about others’ travels. We drove part of Route 66 in Arizona about 10 years ago and stopped at a charming shop called Historic Seligman Sundries. I’ve seen conflicting information online about whether it’s still open, but I hope you and your family get the chance to drive the entire route someday.

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    1. Thank you, Rose. It was super fun. One of the stops in Illinois is permanently closed because the owner died a couple of years ago and the family is not interested in keeping it open. We drove by anyway and the signs are still up, so we took a picture of it. I hope we are able to drive the entire route to California. I think it’s going to be an awesome experience.

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  25. Sounds like my kind of adventure, Edward! Last week, I was driving though rural Wisconsin, in an area I’m not familiar with, and passed a sign for what I thought was Route 66. Interesting, because Route 66 does not, nor did it ever, run through Wisconsin. I googled it later and learned it was STATE HIGHWAY 66. False advertising, guys! And not nearly as exciting.

    Hope you had a great birthday!

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  27. Oh my goodness — I didn’t even realize that route 66 went so far north. I guess I imagined it like our current highway systems that go east/west. How interesting! And 23 towns in 3 days. That is incredible. Love all your fantastic pictures – what a cool adventure. And happy birthday, my friend!! Here’s to an incredible year ahead!

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    1. Thank you so much, my friend. I realized the true scale of that route during our trip to Springfield when we saw the whole thing on the map. It was incredible, especially seeing that it starts in Chicago! We couldn’t miss the opportunity to drive the Illinois portion. It was the perfect trip to celebrate the 4th of July weekend and my birthday. I know you and the kids are still traveling, so stay safe!

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  29. Edward, this is such an awesome adventure. I honestly can’t believe I haven’t visited this place yet. You just gave me a reason to plan a vacation and a road trip 😄

    I love how you turned a simple stop at the Illinois State Fairgrounds into a memorable Route 66 journey. Visiting 23 towns in just three days, collecting passport stamps, and exploring the history of our home state sounds like an incredible experience. Your photos and story really capture the spirit of the Mother Road.

    Wishing you many more amazing and memorable adventures ….

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    1. We had a lot of fun. Even if you just take one day to visit some of the markers and museums in Chicago and Joliet, it’s worth the time. It’s a great, inexpensive family trip. Thank you, Willie.

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  30. Hmm, such an interesting post! I feel like I’ve come across this place before, and I even remember seeing a celebrity being interviewed near this Illinois bridge. Strangely enough, I’ve also had dreams about the road splitting before reaching the bridge. God knows why, but it stayed with me.

    Loved the article though, thank you for sharing! ✨

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    1. You’re very welcome. Wow, that was a strange dream. Well, there were some parts of the road that were under construction, so maybe it was the future that you saw.

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  33. This past April, on our trip home from our winter in TX, we took the Texas panhandle section of Rte 66 from Amarillo to Shamrock. We decided to do this in celebration of “The Mother Road’s” 100th birthday and saw many fun and interesting historical landmarks and oddities. I made a couple of posts about our stops. In other years, we’ve been on various segments in other states, but had never before actively sought out the quirky stops. On our way back south this fall, we hope to see more – particularly in Oklahoma- the state with the longest stretch of the route. You did a great job of seeing, photographing, and recapping so much of the beginning of Route 66, Edward. I hope you get to realize your plans of seeing more of it and I look forward to your posts of the experience.

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    1. Thank you, Terry. I always forget to take photos when we go on trips, but I took plenty this time because I wanted to share them with my WordPress community. I’m glad you enjoyed them! This route is so much fun, especially if you use the passport booklet to get stamps from the different stops along the way. Your trip south this fall sounds like is going to be fun and I look forward to seeing your photos.

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  34. A fascinating travel reflection that combines history, local culture, and roadside attractions, offering readers an enjoyable glimpse into Springfield and one of Illinois’ memorable Route 66 landmarks.

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  35. What a light, fun, and cultural adventure, Edward! I am sure you will all remember it for life! Loved the full family photo (with dog) by the Route 66 mark. Thank you for sharing these unique and legendary moments with us. I guess this was such a special birthday for you, my friend! Wishing you health, joy, growth, and fulfillment for the next lap around the sun and, as always, sending light and blessings your way! Happy birthday! ✨🙏🍀🌞

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  36. What a wonderful journey through history! Your post beautifully shows that Route 66 is much more than a highway—it is a pathway to stories, memories, and a deeper appreciation of America’s heritage. The photographs bring the adventure to life, making readers feel as though they are travelling alongside you. Thank you for sharing this inspiring blend of history, family, and exploration. Wishing you many more memorable miles on the Mother Road!

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  38. Wonderful way to celebrate your birthday and learn more about your home state. Should you decide to complete the journey sometime in the future and I’m still around, I’d love to meet up with you and your spouse at the termination spot in Santa Monica, California 🙂

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    1. Definitely! What impressed me was how well these towns are embracing these stops and maintaining them. Everything was clean, with plenty of parking, and the people were super friendly, even letting the dog inside some of the shops. We had a lot of fun.

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    1. Thank you, Brad. It was a lot of fun. The garden was beautiful, and we definitely need to go back. I tell you, sometimes it’s better to just go without a lot of planning. It was better than what I had imagined.

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  48. What a great way to celebrate the 250th! Did you make your son listen to multiple versions of “Get Your Kicks on Route 66” in the car and sing loudly to annoy him? That was my specialty! 🤣

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      1. I don’t know what your budget is, but things like light bulbs cost enormously for the newer models, and repair people assume their owners have lots of money, so those bills triple. Mine’s a well preserved ’99, and engine maintenance is about what you’d expect for a 1 ton pickup. It’s also from the days when they built with real wood, so the interior is very homey.

        If you’re thonking about buying used, I would do it very soon. Current economic changes have people selling them low, trying to make mortgage, but coming economic changes are about to put these in high demand as homes instead, and their price will rise accordingly.

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  52. I’ve run close to this route a number of times while crossing the country, but always under circumstances in which time or funds, or both, prohibited its full enjoyment. I’d love to drive it someday.

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    1. Thank you, Ana. I totally understand. I think we drove through portions of this route in the past but never thought about the historical aspect of it. It was nice to drive through some of the towns and meet some great people.

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  53. I have heard about Route 66 my whole life (partly due to the song about getting one’s kicks on Route 66) but never knew that it starts in Chicago and ends in Santa Monica. Or that it was built one hundred years ago! Thanks for this mini-vacation via your blog commentary + photos. One of my great grandmothers and great grandfathers drove across country with their six teenaged children in the early days of automobile transportation. They started in New York State and ended in CA; so maybe their auto-adventure included route 66…

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    1. You’re welcome, Will. Thank you for sharing about your great-grandmother and great-grandfather. I’m sure they drove a portion of the route on their way to California. I’ll tell you, there is so much history in our towns and cities, and the people are so proud to showcase it to visitors. It was a great trip.

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  55. What an epic trip! Great pix and narrative, looks like you had a fun time. I’ve done from Santa Monica to Albuquerque with the rest as a bucket list item. I’d like to someday also take AmTrak (“The Southwest Chief“) from Chicago-LA. 😎

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    1. Thank you, Darryl. It was a lot of fun. It’s really cool that you did the Santa Monica to Albuquerque part. We are thinking about doing the rest in an RV versus staying in hotels. We think it will be more fun that way.

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    2. Hey Darryl.

      I highly recommend that you try an Amtrak rail pass. I did this back in Spring and stopped in ABQ (and then completed the Southwest Chief route to Chicago the next day).

      See my guide if you want to know more about the USA rail pass – especially when it goes on sale!

      See you on Amtrak!

      James

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      1. James, thanks! Very cool. I read your post, really interesting and informative… wow, that’s huge drop in riders from the 1920s. But I think trains are a lost art, they’re not for everybody… but IYKYK…they go places you never see from the car, it’s unhurried, the other passengers get it as well. Nothing better than a cold one in the dining car as you wind around a turn and there’s a river… 😎👌 Thx again for the tip, will def check out the pass!

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