Roadtrip 2021 - Route 66, Chicago to Los Angeles (getting started)

My wife and I decided to take an extended road trip during July of 2021. We drove the entire historic Route 66 from Chicago to Los Angeles.

This 2.448 mile trip, crossing 8 states is very doable, but has some challenges that can be minimized with good planning... 

I spent an entire year planning the trip, but became discouraged with much of the literature and blogs that I found inaccurate, hard to understand and easy to become lost in confusing detail, which makes it difficult to see the bigger picture, and how an efficient, enjoyable trip can be accomplished.   

Over the next year, I plan to add blog posts from my perspective to enable some insight into my trip with tips that may make it easier for those who may want to take this fabulous journey. 

Our trip lasted 10 days on the way out (we drove Chicago to LA), and we believe we experienced Route 66 in a most thorough way. We took a break in Santa Fe for 2 days (a brief departure from Route 66), but this was a great time and much needed resting spot. 

These are the kinds of diversions and worth doing side trips that the "purists" do not usually talk about; I find many books only focus on the road itself, are overly wordy, hard to follow, and offer poor translation to what you will actually experience. I believe and hope you will find this useful.   

This blog will cover the journey and experience from Chicago to LA, but if you travel LA to Chicago, simply reverse the  journey.  

Route 66 Begin Sign

Route 66 begins on E. Adams Street at Michigan Avenue (directly in front of the Art Institute of Chicago). If you stand in front of the Art Institute and walk due west, on the southside of Adams Street, you will run into the "Begin Sign" about 100 feet from Michigan Ave. on the Southside of Adams.

To see the "original sign" which is on the corner E.Adams and Wabash, continue walking due west in the same block to the first corner (Chicago "L" train) runs north and south at this intersection - if you cross the street (Wabash) and go under the "L" you have gone too far.  

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