Route 66 Illinois (Part 1)

Route 66 Sign Chicago

Route 66 Illinois - The Start

Route 66 Illinois and the city of Chicago is the official start to the route. Not only is the "official" start sign it's also the state I think with the most things to do. From the city of Chicago that we loved, through to places like Pontiac (yes the home of Pontiac), the State capitol of Springfield, Joliet and Wilmington.

If you are doing the more traditional route of East to West (like we started our journey). You'll get the sense of the whole trip starting and the enjoyment that's to come. There is so much history on this part of the route, you'll struggle at times to know when to stop and start! Because there is SO much in Illinois todo I've split this post into 2 sections. This part takes you to Springfield the state capitol. The next post is Springfield to St Louis.


Route 66 is probably the most famous road in the world. Generations of traveler's have romanticised this highway as a symbol of unlimited mobility and freedom of the road. Its iconic status is enhanced by the unprecedented volume of music, books, films, and other art forms that depict it as the essence of America's highway culture.

Route 66 was born in 1926 as part of the new numbered highway network and quickly grew to be the preferred road west. U.S. Highway 66 was not as old or as long as some other transcontinental routes like the Yellowstone or the Lincoln Highway but it quickly gained fame as the shortest, year-round route between the Midwest and the coast as it passed through the fabled landscape of the American Southwest. The construction of this thin, ribbon of road helped to transform the American West from an isolated frontier to an economically vital region of the country and made it accessible to anyone with a car.

By the 1980's most of the Route had been bypassed by Interstate and larger roads and the Route started to take on it's Second life as a tourist destination for many from around the world. Buildings started to open up again, towns that were like ghost towns years previous started to open up.

Chicago is the start of Route 66 Illinois and this is where we started our epic journey...

Route 66 Map Illinois
Route 66 Sign Chicago


Although not the state Capitol of Illinois, Chicago is the biggest city in the state. Home to President Obama before he entered the White House, the city has a proper ecliptic style of buildings. To me it feels a mix between a European and USA city. It's got a great arts scene, good night life, river that runs through it, big parks and museums. It's also got one of the tallest buildings in the USA in the Sears Tower.

After our flight from the UK on British Airways we collected our Ford Mustang (a must for Route 66) hire car from the airport and made our way to our accommodation. With no "iconic" Motels or Hotels to stay in we bedded down in an Air B+B for the 3 nights that we had in the city with plenty that we wanted to do.

What to do in Chicago

There is loads to do in Chicago. Whilst I could say and list everything that you should do, it's not like the rest of the route where it's just one or two things. It's a big city and you could spend weeks here and not see everything. What do I recommend? Well first off I think in big cities it's worth jumping on an open top bus tour. We did Big Bus Tours trip which was both funny, informative and gives you a real good indication to what you do want to see in the city and what you don't.

We had a wonderful lunch down by the river watching the river traffic go by. It also gave us the idea of getting on one of the river boats. These tours are Architecturally based around the rivers seeing the different sides to buildings that you might not from the street. Well worth the 90 mins or so these take.

Other things that's worth looking at as well is dinner up one of the towers. We did dinner at the Signature Room, although the steak we had was a little disappointing. It might be worth looking at other options. A must for dinner though would be to have a famous Chicago Pizza. This isn't like any other Pizza that you might have elsewhere. It's a proper "deep dish" and actually more like a Pie than a Pizza. As our first taste of American portions and these deep dishes we only got about a 1/4 of the way through it - they are massive!

Down town Chicago
Down town Chicago
Cloud Gate Chicago
Down town Chicago
Down town Chicago

Chicago - Continued

Chicago is home to a number of sporting teams. The Chicago Bears play in the NFL. Chicago Cubs play in the Major League Baseball League. We went at the time of year that the Cubs were playing rather than the Bears. Having never been to a baseball game at all in my life this was definitely something to tick off the list! Whilst the game went on for nearly 3 hours it was great to see the pre match pomp, the merchandising for everything (which we fell for) and the passion of the supporters! It was bonkers to see a full stadium on a weekday - I did wonder what job everyone was missing from to be at the match!

Other things to do

Millennium Park is a new part of the town (it's really close to the official start sign as well) it's a big open space, and also contains the Chicago Bean (official name Cloud Gate) but it's a great place for a good photo! Also worth looking at is all the trains that run around the top of the buildings and bridges - they make some good photo ops as well.

Evening time should be spent either up one of the towers as the sun sets, or perhaps down at Navy Pier. It's home to a number of different restaurants, things to do, shops and a good evening out.

Depending on what time of year you get to the city make sure you look at things on. We were there at a time of a whole lot of buildings lit up at night - which was great to watch. There is LOTS going on in the city!

Wrigley Field
Chicago Lights

Leaving Chicago...

We made a detour via the Indy 500 - now of course this isn't something for everyone, however it was a major part of the planned trip. For the 500 we did the drive down from Chicago and then back up again. We didn't immediately pick up from exactly where we left off. But we did drive to the outskirts of Chicago to start our Route 66 journey. If you don't have a car it's also possible to do that journey by bus - have a look here!

The first thing to strike me about this was the open space. We had spent the last few days in Cities with sky scrappers, bustling city life and then we end up with miles for nothing to see or do! Our first planned stop on the route was the town of Joliet. We visited the Joliet Historical Museum which gave a really good history to the area and about some of the famous people to have come out of the town. It also started our obsession with stopping in the gift shops... Now this is a very expensive hobby on Route 66 if you stop at everyone. However it's well worth keeping the memories!

Just outside of the town is what Joliet is probably most famous for and that's a prison. Now you probably wouldn't know it - but as soon as you see it you'll know its been used for both the Blues Brothers film and also the hit TV show Prison Break. It's possible to get a tour around it - we didn't do it but if you are a fan of either shows it's well worth it I've been told!

Past Joliet

On leaving Joliet the next must stop on the Route is the town of Wilmington. Only 17 miles down the road - but this is what we started to see as the true Route 66 environment. A building and a place that's properly cared for and loved by the locals, caring about Route 66 and all the history about it.

You have to stop at the Launching Pad restaurant and have lunch. It's the home to the Gemini Giant. These structures will crop up at a number of other places along the route - but the Gemini Giant is one of the more well known. The rest of Wilmington is a nice wide road, with some murals on the side of buildings which are well worth getting photos of.

Joliet Prison
Wilmington Route 66 Illinois
Gemini Giant Route 66 Illinois

Wilmington Onwards

As you leave Wilmington you start to see all sorts of things "crop up" on the route. Lots of old cars at the side of the route. Perhaps the odd restaurant that you might like to pop into, or perhaps an old disused (or indeed refurbished garage). We initially took pictures of EVERYTHING!! Then we stopped at EVERYTHING and then realised if we were going to continue like that we wouldn't get to California in time at all!

That's not to say you shouldn't stop. Absolutely you should and don't dismiss them at all but at the same time if you stop and look at every possible thing you will need months to complete the route...

Tom's Place

There was a cool old garage in Dwight that we stopped at with a load of old Machinery in. The next "must stop" though was with Tom's place called the "The Shop on Route 66". Tom who's the owner welcomed us in to show us his collection of old items, signs, and his glass making. He's so lovely and knows the Route and all the characters along it. This is where also we started to learn about the "family" nature of the Route. Everyone knows everyone and people have a real sense of history about it. Tom takes your photo and he add's them to his gallery of pictures. You'll also need to sign the guest book another regular thing you'll get used to on the route!

The Shop on Route 66 Illinois
Old car in Pontiac Route 66 Illinois
Statues Route 66 Illinois
Old Garage Route 66 Illinois

Pontiac Onwards

If you know your cars you'll know the name Pontiac. Although it's a brand name that's now disappeared the Pontiac Firebird was up competing with the likes of the Ford Mustang and Dodge Challenger back in the 70's. Well the car brand originated from the town of Pontiac and there is a great museum with a number of their historical cars in it. The town of Pontiac is also well worth a look around. With lots of small little cars lining the streets, through to some impressive buildings it's worth spending a bit of time here. It's also worth looking out a number of the murals that line the town streets which give a throw back to an older time.

Past Pontiac

Outside of Pontiac there isn't a huge amount of things "to do" as it were before you hit Springfield. There's a little stop at Chenoa where there is a cute little stop and a information point inside a shed! Lots of murals and structures continue to line the main road and again it's worth stopping for photos if you have time! It's also the first part when we started to hit the Old Route. No longer on roads that were wide some of these parts of the route were more narrow tracks that were from a bygone era.

Spragues Service station is worth a little stop. Although there are multiple old garage's Spragues is a great example. Earlier in the post you'll have seen the Gemini Giant well in Atlanta (no not that one) you have Bunyons Statue that's worth a photo op. Created in 1966 as an eye-grabbing restaurant advertisement along Route 66, the displaced muffler man known as Paul Bunyon still holds his precious hot dog for all to see even after being moved from his original spot.

Elkhart for us was the first time we couldn't believe how deserted places were. We drove through at about 7pm and it was like a ghost town! Still again more garages to see on the route around here!

Before Springfield

Just before you get to Springfield is Oak Ridge Cemetery. Now usually I wouldn't suggest going to a Cemetery but this one contains the tomb of the 16th President of the USA Abraham Lincoln. It's an impressive structure fitting to one of the more famous presidents.

We've now hit the outskirts of Springfield and Route 66 Illinois. I'm going to cover this in Part 2 which by the end of it will have got us all the way to St Louis and the first change of state!


Bunyon Structure Atlanta Illinois
Atlanta Illinois Route 66
Lincoln Memorial Route 66 Illinois
Ford Mustang on Route 66 Illinois


  1. Betty Jane Partin
    May 10, 2020 / 5:27 am

    Really enjoyed reading this. We are planning to take this trip in September of this year. Thanks for all the tips in where to go . Looking forward to reading part II .

    • Ben
      May 13, 2020 / 9:32 am

      Thank you for your kind words! Part 2 is now live. I’ll continue to post the other states as we go! Hope you have an amazing trip.


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