Cruising Down Route 66: A Journey from Chicago to Springfield

Starting the Adventure in Chicago

Our Route 66 road trip began at O’Hare. Chicago airport as we decided that would be a better option than starting in a major city. We booked the car for 2pm which in hindsight was a little late and nope, they would not alter the time when we turned up 2 hrs early. We picked up a massive SUV (see Facebook group pictures) and set off. Karen did the driving today and did amazingly well, one wrong turn getting out of the airport but only a small detour and only 1 “honk” from another driver all day for going slow and not indicating quickly enough. USA roads are different to ours that for sure but so far so good.

A 'Pit' Stop at the Roadside Diner

Just a couple of hours into our drive, we stumbled upon a charming themed roadside diner. This quintessential Route 66 stop was like stepping back in time. The diner's retro decor and friendly staff made us feel right at home. We couldn't resist ordering classic American fare – grilled cheese sarnie and Matt opted for a stack of very messy chicken wings covered in sticky sauce. We were happy to tip with such great service and friendly staff, it’s a shame it’s the norm over here as some places we have been we have been met with grumpy staff, hardly any banter and it’s still expected.

Reflections on the First Leg of the Journey

Driving from Chicago to Springfield on Route 66 was an unforgettable experience. The road is more than just a journey; it's a nostalgia-packed adventure through America's heartland. We really enjoyed just meandering down through the towns and looking at all the local homes etc. Between towns you drive down route 66 with the rail road on one side and the main highway on the other for a lot of it.

I think we could have planned better and set of earlier…..a lot of the route 66 shops etc are only open until 4. We perhaps rushed this leg a little as weren’t getting into Springfield until about 7.30pm so didn’t stop at a lot of the tourist spots. We still managed to get lots of pictures (see Facebook group). Tomorrow will no doubt have loads more pictures as only a 3 hrs drive to the next stop so we can take our time.