Route 66 – The Beginning – Illinois

Fun Fact: The oldest hotel on Route 66 is the Eagle Hotel in Wilmington, Illinois. Though sitting empty today, the 1836 hotel once serviced stagecoach travellers, has plans of restoration.

Whoop, Whoop, welcome back to the next instalment on this wonderful trip through the famous Route 66. I decided the best way through this journey would is to do it state by state.

Illinois was our first state and where Route 66 begins in Chicago. It was our first time to Chicago the windy city and I honestly didn’t know what to expect but I have to say I was pleasantly surprised at how beautiful it was with its clear blue skies.


I loved every moment in Chicago and I would not mind going again to spend more time understanding this beautiful city. I enjoyed walking around the centre and seeing street performers and experiencing how friendly everyone is. For me if the people are not friendly, wherever I go it can ruin an experience of any location as the people make it what it is. Yes, we go to see the historical sites, try new food and say we have been there BUT the people is the foundation and we should never forget that.

I am going to digress a little but I need to get this off my chest. On the flight to Chicago from London, the flight was half full or half empty however you see the world. As per usual I always make sure I get the window seat especially for a long flight so I can snuggle up to the window and have a good snooze. A gentleman sits next to me, I was fine with it and hoping when the seatbelt sign comes off he would move. No, this man did not move. He did not move. I looked around me and saw EMPTY rows, I mean full on empty rows and this person did not move. I waited 45 minutes to see if this person would move. They did not move. I was slyly fuming and decided to move, before I even settled into my empty row he had made himself comfortable over my former seat. I was not impressed! Good, got that off my chest, now back to Chicago.

To get a feeling of Chicago we went for a long walk with no destination in mind and seeing where we ended up. We discovered this museum which I am starting to believe used to be city hall. It’s shame I didn’t take down the name but here is a picture for you to enjoy.




However, the best thing we found in Chicago was the “Chicago Jazz Festival” I am not a fan of jazz but I loved the vibe, the music and the art.



Food Food Foood!!!!

Look what we found Portillo’s  now this place serves dogs, dessert, pies, sandwiches and burgers. I came for one sole purpose. A Hot Dog. I was disappointed, I do not know how I got this image into my head but I was expecting a large Hot dog but instead it was small, I think it fitted in my hand. (I have small hands). It did taste nice but I wanted a big dog. My craving for a hot dog had yet to be satisfied. On the upside I had a large beer.




We made the decision not to start exactly at the beginning of Route 66. For our first time driving in America we thought we would start easy and avoid the city rush.

With our trusty Lonely Planet “Route 66 Road Trips” guidebook we started our epic journey.



Small girl problems!


There were no major attractions but more of a pit stop as a chance to eat, comfort break and stretch these tiny legs.

Palm’s Grill Café opened in 1934 and was literally situated along Route 66 and has served many travellers over the years and I hope it continues to do so for many more years. They served the best pie I had the whole trip and I mean the best pie. So, after watching Supernatural and always seeing Dean Winchester always talking about pie, I needed to see what the big deal about pie was. I was not disappointed in the slightest bit but others not so nice. Look at this peach pie and across the road Tall Paul.



Springfield was my most disappointing stop everything we wanted to see was closed. Lincoln’s Tomb we got there just after it closing and I was looking forward to seeing such an important figure in history. Also, the Cozy Dog Drive-in was closed, I was on another hunt for a hot dog. Yes, this trip was slyly focussed on all the things I could eat.



Next stop Missouri!!!


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