Walking Western: A 24-mile Journey

There’s an unassuming point on Howard Street where Asbury Avenue enters the City of Chicago and turns into Western Avenue. Chicago’s longest street continues for about 24 miles, creating a long streak through the city and touching or intersecting 16 of Chicago’s 77 community areas along the way. Western is a line of fixation. 

Since I came to Chicago, I had the desire to walk the whole street. I wanted to see what I came across and what I thought about along the way. In a sense I’ve seen it as a pedestrian’s pilgrimage of sorts. I thought, maybe, I’d find some deeper meaning through these travels, or at least learn something new about the city. And honestly, I just wanted to say I did it. 

I’ll be up front, I didn’t walk the whole avenue in one outing. I split my journey into four days to make the hike a bit more manageable. I should note that this quest isn’t entirely unique. Seven years ago, two Chicagoans shared a documentary in which they walked all of Western Avenue, drinking at 64 bars along the way. 

I didn’t have a set list of places or people to visit on my walk. I wanted to capture, if possible, a spontaneous moment in Western Avenue’s long history as viewed from the street.  

Anyway, I now present my journey along the entirety of Western Avenue in Chicago.

Day 1

Day 2

Day 3

Day 4


All things end. Well, Western Avenue doesn’t actually end at 119th Street, but Chicago’s boundaries do. The avenue continues south for several miles until it becomes Dixie Highway at around 147th Street. 

It is a bit fitting that the intersection at the end of my trip reminds me of the one where I began — there’s a Walgreens and a McDonald’s that greet me, and honking horns that do not. Yet now, standing 24 miles south, I also feel like I’m in a different world altogether. 

Chicago’s complexity manifests along its streets, which dart unwaveringly through our neighborhoods.

What happens when we reach the end of the road? I guess we turn around, and walk back home.

Western Avenue goes north from 119th Street. Christopher Silber, 14 East.

Header image by Christopher Silber, 14 East