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.  

Top Photo 

Route 66 Begin Sign

Photo is looking due west, on southside of E. Adams Street

The Art Institute of Chicago + Michigan Ave. is directly behind me (500 feet or so) as I am taking this photo 

Notice you can see the "L" in the background running north and south on S. Wabash Ave.

Bottom Photo

Original or "First" Route 66 Begin Sign 

Photo is looking due west, notice "L" train in background.

This is at southeast corner of E. Adams & S. Wabash

The sign is straight down from the newer Route 66 Begin sign - it is surrounded by black fencing.

If you walk under the "L" at S. Wabash Ave. you have gone too far.

Route 66 End Sign

If you are traveling the route east from LA to Chicago

Above Photo

If your traveling from LA to Chicago this is where you will end on E. Jackson Drive just before you get to Michigan Ave.

Notice Millennial Park in background 

Note: even if you are traveling Chicago to LA you should still walk around the clock and see this sign since it is the official end in Chicago

All three signs on the same block, (simply make a circle around the entire block east of the Chicago Institute of Art and you will see all three signs) 

Begin walking west in front of the Chicago Institute of Art, turn south (left) on  Wabash (at the "L), walk one block south on Wabash to  E. Jackson Blvd. turn left (heading east) and the sign will be on the southside of E. Jackson Blvd. Walk anther 100 ft, turn left (heading north on Michigan, and you will end back in front of the Chicago Institute of Art

The entire walk to see all 3 signs is 10 minutes. Simple start in front of the Chicago Institute of Art and circle the block just east as described