This post is part of a series I’ve done on Route 66. In 2022, I drove the entirety of Route 66 from Chicago to Los Angeles. 2500 miles, 8 states, countless stories, and an endless stretch of small towns, neon, diners, motels, and roadside attractions. Read through all of my Route 66 posts here. They’re also linked at the end of this post. If you’re planning your own Route 66 road trip, either the whole thing or just a part, I hope these help you out. Enjoy the drive!
On my big Route 66 road trip this year (I drove the entire 2500 miles), I think the stretch through Illinois surprised me the most. Living in Tulsa, I was already pretty familiar with Oklahoma, Missouri, and Texas. I had high expectations of New Mexico and Arizona (for me, that’s the peak of Route 66), but I had relatively low expectations of Illinois. Actually, I’d never even been to Illinois.
But I really enjoyed it! Having never been to the heart of the midwest before, the miles and miles of cornfields and big time farming operations were really something to see. Throw in the big city experience in Chicago that starts the trip off with a bang and add 300 miles of small towns, roadside attractions, and historic sites and you’ve got a great start to your Route 66 trip.
I’ve written pretty extensively about my Route 66 trip and you can read my play by play posts on Chicago and the Chicago to St. Louis (aka Illinois) stretch, but this post is more of a postmortem or a post game wrap up, if you will. I’m writing these state by state posts to recap what I liked, what I loved, what I wasn’t very impressed with, etc.
I’ve got notes on what turned out to be my favorite spots and favorite restaurants plus recommendations of what I’d do differently next time. And I’ll also make recommendations on places that I would actually stay (because I’m not usually a $79/night motel kind of gal).
Illinois Route 66
Okay, here we go…
Route 66 Towns in Illinois
Let’s start off with a list of towns that Route 66 passes through in Illinois so you can lay it out on a map. This is NOT every single town, there are just the ones that I personally found to be the most noteworthy.
My Favorite Illinois Route 66 Attractions
Route 66 Beginning Sign: Downtown Chicago
If you only have time for one stop in Chicago, this is the one you definitely can’t miss. You’ve got to have that photo opp at the start of your adventure!
Gemini Giant at the Launching Pad: Wilmington, IL
This is my favorite of the giant “Muffler Men” along Route 66 so far. The Launching Pad was closed when I came through here, and I’ve heard that they’re not going to be able to reopen as a restaurant anytime soon, but are going to be running the gift shop regularly.
Route 66 Illinois Hall of Fame: Pontiac, IL
Located in a historic brick fire station, this is one of the better done small museums along the Route. While the Route66 Illinois Hall of Fame is the main draw, there are actually a series of museums in the complex (so don’t forget to go upstairs) and plenty to see in the alley/courtyard out back.
There’s a lot to see here, but the absolute don’t miss is Bob Waldmire’s VW van. Bob is a Route 66 icon (an artist who spent much of his life traveling back and forth on Route 66 documenting what he saw) and the inspiration behind the Fillmore character in the Pixar movie Cars.
And I also really loved the part upstairs where they recreated a home from the 1940s.
Pontiac Oakley Automobile Museum: Pontiac, IL
So far this has been hands down my favorite car museum on Route 66 and I’m sure it’s partly the building. Located on the town square, it’s a historic building that still has the original flooring, tin ceilings, and dark wood paneling. Add all of the cars and little vintage vignettes and it’s SUCH A COOL PLACE.
World’s Largest Covered Wagon: Lincoln, IL
This is a roadside attraction at its finest.
Turkey Tracks on the Route: Girard, IL
You’re going to think I’m crazy, but this just might have been my absolute favorite Route 66 stop in Illinois. I’d read about this in one of my guidebooks and it felt like we were on a wild goose chase down old country roads surrounded by cornfields looking for turkey tracks, but when we saw this we just burst out laughing. 10/10 don’t miss!
Henry’s Rabbit Ranch: Staunton, IL
Many people are a little disappointed to learn that the rabbits are actually VW Rabbits half-buried Cadillac Ranch style (although I’ve heard that maybe there are also furry rabbits inside that he’ll show you if he’s home).
Chain of Rocks Bridge: Illinois to Missouri
I’ve gushed about the Chain of Rocks Bridge plenty in this post, but basically, I think walking across the Mississippi River on the Chain of Rocks Bridge is a don’t miss.
Where I Ate, What I Liked & Where I Would Go Next Time
Let’s start with where I ate and what I thought…
This famous diner has been serving breakfast and dinner to hungry Chicago patrons and Route 66 travelers since 1923. I twisted around my travel plans pretty to hit up Lou Mitchell’s (closed Monday and Tuesday), but honestly…so far, this has been one of my more disappointing experiences on Route 66. Which is a shame because everything about it seems like something I would like. I think the experience really hinges on your server (ours was really struggling and there was some attitude), because most tables not in our section looked like they were having a better experience.
Anyways, I would still give it a try, but just be prepared for an above average breakfast price and the potential for hit or miss service. Lower expectations always yield better results ; )
Old Log Cabin: Pontiac, IL
I’ve eaten in a lot of roadside dives along Route 66, but so far this is the best burger I’ve had. It’s charbroiled and oh so delicious.
Cozy Drive In: Springfield, IL
I singled this out as my must eat place in this section of the route (it’s a rule that you have to eat at least one greasy/fried meal a day when you’re driving Route 66 ; ) and honestly the food was just okay, but it’s a really cute place with a lot of history (and plenty to read about different places inside).
Weezy’s: Hamel, IL
Originally opened as the Tourist Haven in 1938, this little roadhouse has been serving up good food ever since. Famous for their fried chicken, I would also recommend the catfish.
Places I Would Try Next Time
Family owned and operated for over a century, the Berghoff has been serving traditional German food since 1898. They were also Chicago’s first liquor license granted after prohibition ended. They’re closed Sunday and Monday (of course when I was there), so I didn’t get to try it, but they’re open for lunch and dinner (I gather there’s a more casual cafe and a more formal restaurant all in the same building). The location is really convenient to a lot of downtown attractions.
Dell Rhea Chicken Basket: Willowbrook, IL
Serving fried chicken dinners since 1946, it’s a very cute place (such an iconic sign!), but it’s in a super weird location. It fronts I-55, and you have to go through a new(er) built shopping complex (Target, Starbucks, La Quinta, Denny’s, CVS, etc.) to get to it so it’s not on a quaint stretch of Route 66, but once you get back there, it’s CUTE. I wasn’t passing through at the right time to stop on this trip, but planning to hit it another time because it looks like the kind of place I would like.
Deck’s Drug Store: Girard, IL
This place looked super cute and I’d definitely plan a stop next time I’m through here.
Ariston Cafe: Litchfield, IL
One of the oldest continuously operated restaurants along Route 66 (since 1924!), this is a great place to stop if you want the Route 66 history but more options than the usual greasy burger joints.
Jubelt’s Bakery & Restaurant: Litchfield, IL
In business since 1922, besides all the legendary sweets, they are a full service restaurant with plenty of options like soups, salads, and sandwiches besides the diner classics.
Places I Would Actually Stay
I’ve mentioned before, but most of those $79/night roadside motels just aren’t for me. It has to be something pretty special to peak my interest and mostly I prefer something a little nicer.
Honestly, in all of my research, I haven’t come across a vintage or historic motel in Illinois that I would personally stay in. So of course I’m not going to recommend any of them to you!
Here’s the deal, in Chicago you’ve got sooooo many options so I would opt for something nice to start your trip.
I stayed at the Gwen and really liked it, but if you want something more historic, try the Blackstone which has been hosting presidents, celebrities, and even a few mob bosses since 1910.
I stayed overnight in Bloomington and there weren’t a ton of options but the Courtyard Marriott was decent.
I spent a couple of nights in Springfield because I wanted to see some of the Lincoln attractions and I was honestly surprised they don’t have better hotels. I ended up staying at the Courtyard Marriott which didn’t look great from the outside but my room was completely renovated and great. The Doubletree is probably your best bet downtown. I also stumbled on the Inn at 835 but just couldn’t make my mind up about it. But it might be worth checking out.
It’s four hours from Chicago to St. Louis on the interstate so it’s probably too much to do all of Illinois in one day, but once you get to St. Louis there are plenty of great hotel options.
Other Things to See & Do in Illinois BESIDES Route 66
This section is really important to me, because the whole point of driving Route 66 recreationally was to See America so besides all of the vintage, kitchy, and historic attractions on Route 66, I like to spend a little time focusing on what you might be able to see and experience in each state that’s unique to that part of the country. Now I’m not going to have you running all over the state, but here are a few suggestions that aren’t too terribly far off the route:
Abraham Lincoln Sites
If there’s one thing Illinois is associated with more than anything else, it’s the 16th President of the United States, Abraham Lincoln. I’ve written a huge post here that’s a round up of pretty much every Abe Lincoln site and attraction in the state, but on your road trip, I would focus on the Presidential Library and the Lincoln Home National Historic Site.
Chicago is one of the greatest cities in the US and if you’ve never been before you’re definitely going to want to spend a few days before you start your road trip. Read this one day in Chicago post inspired by Ferris Bueller’s Day Off. But in general some things you might consider are: an architecture boat tour down the river, the Chicago Institute of Art or Field Museum or Shedd Aquarium, deep dish pizza, a game at Wrigley Field, and the SkyDeck at the Willis Tower.
Frank Lloyd Wright Sites
Frank Lloyd Wright fans, or just people who appreciate architecture in general, may want to spend a little time visiting some of his more famous buildings in the area. His studio is in Oak Park Chicago and there’s a large concentration of his houses in the midwest including Illinois.
Besides Oak Park and the Chicago sites, make time to see the Dana Thomas House in Springfield. You can tour the inside of the home on a guided tour.
More Route 66 Illinois Resources
In all of my planning, I found some pretty good resources on the internet so I thought I’d share them with you here:
Illinois Route 66 Itinerary (this one is really good)
Illinois Route 66 Guide Map (with photos)
Locations for All of the Wayside Exhibits in IL (the historical placards)
Visitors Guide & Business Directory (108 page travel brochure)
The First 100 Miles of Route 66 (Chicago, Joliet, Wilmington, Dwight, Pontiac)
Cruisin’ with Lincoln on 66 (Bloomington/Normal)
Logan County CVB (Lincoln, IL)
Visit Springfield, IL (CVB Website)
Planning a Route 66 road trip? I’ve got all of the info you need!
I’ve written about my cross country road trip pretty extensively section by section. Read them all here: Part 1 (Chicago), Part 2 (Chicago to St. Louis), Part 3 (St. Louis), Part 4 (St. Louis to Springfield MO), Part 5 (Springfield, MO), Part 6 (Springfield, MO to Tulsa), Part 7 (Tulsa), Part 8 (Tulsa to OKC), Part 9 (OKC), Part 10 (OKC to Amarillo), Part 11 (Amarillo), Part 12 (Amarillo to Albuquerque), Part 13 (Albuquerque), Part 14 (Albuquerque to Flagstaff), Part 15 (Flagstaff), Part 16 (Flagstaff to San Bernardino), Part 17 (Los Angeles).
I’ve got the scoop on where to stay including the best Route 66 motels recommendations.
And finally, my final trip recap where I spill the beans on how many days you need, the best itinerary, my favorite don’t miss spots, and other tips.