Route 66 is definitely one of the most iconic and important highways in US history. It served as a major path for those who migrated west when California was seen as the promised land during the Great Depression. The golden era may long gone but the romance of Route 66 continues to captivate people around the world. It’s an unforgettable trip back in time to bygone America, an era of neon sign motels and mom-and-pop diners.

Realistically, you need at least two weeks to complete the whole journey from Chicago all the way to California; we managed to complete the course in ten days with a hire car but by really pushing our luck with lots of driving each day. If you’re on a gunshot road trip like us, here are a few highlights along this legendary historic road that you don’t want to miss.


Chicago is the starting point of Route 66 but don’t rush as there’s lots to see and do in this ‘windy city’. Chicago is renowned for its stunning art, sculpture and architecture. Take a stroll in Millennium Park and take a selfie with the Cloud Gate, a sculpture that looks like a giant drop of liquid mercury and reflects the whole city from different perspectives. Across the street from the park is The Art Institute of Chicago, which has an extensive art collection on display over four levels in two buildings, including the ‘America Gothic’.

Then kick start your road trip with a skillet breakfast at Lou Mitchell’s, this iconic greasy spoon diner has been serving hungry Route 66 travellers since 1923, it is an important institution of Chicago. Within walking distance, you will find the road sign on Adam Street that marks the official starting point of the Mother Road.

Make a quick stop at the second most populated city outside of Chicago metropolitan area – Springfield, the home of the most famous past resident of United States – Abraham Lincoln.