I have a few I can name that I do my best to avoid ever riding on and last weekend, when I was outside of my normal riding area, I realized my knowledge is pretty limited so I thought I'd post this in hopes to start an ongoing thread of streets that are pretty miserable for riding a bike. 

To get it started...

  • Ashland Ave. - No bike lanes, speeding cars
  • Michigan Ave. - No bike lanes, speeding cars, tourists, gaggles of buses
  • Western Ave.  - Ashland but with cowboy hats ;-)

The other thread... What Are Your Favorite Chicago-Area Bike Lanes, Paths & Routes?

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(And now improved with giant chunks sawed out of the pavement, accompanied by loose gravel, at every interscection!)

Problem is there's no great alternative to Archer to get downtown efficiently...

You are right on both points.  I couldn't believe they left those pits in the bike lane every block without even putting up a sign or some sawhorses.  It would be easy for some unsuspecting cyclist to hurt him or herself badly, especially in the dark.  Now the question is how long it will remain like that.  It has already been too long. 

i know! i keep thinking that too. I'm also dreading the quality of the patch jobs, which I'm guessing won't be pristine. 

Whatever they do will no doubt crumble into cinders soon enough.  When I moved to where I live initially, I rode a Centurion road bike with 23s.  I have gradually moved to 32s, which are doable, but now even a bike with 38s and a moderate front suspension.  When my friends ask me to find bikes for them, I now build in a deterioration factor for the future.  Along with my own deterioration factor, of course.    

Right! Chicago may be a grid, but if you'll look at a map you'll see a giant swath of canals, highways, intermodal (rail) yards and rail lines preventing riders from using the grid to avoid riding on Archer. Unless one wants to take other already mentioned Dreaded Bike-Unfriendly Streets (Cicero, Pulaski, Archer, Western).

I wince when I hear anyone complaining about how rough they have it on the north side, and I groan out loud when our Active Trans decides to spend more time and energy on [name anything on the north side] when the Archer corridor (south/west of Throop) is so utterly neglected and wretched for cycling.

Yes, sir!

Those barriers make riding on the south and west sides a lot more difficult than riding on the north side. A lot of north siders look at us like we're crazy if they've never actually gone south or west and experienced it for themselves.

The industrial legacy is a bear.

I've twice broken parts of my bike while traversing the washboard surface of Archer between Kostner and Kedzie. If it was loose gravel, it would be a better road, honestly. Now, between the utilities tearing up portions and the sewer work, it's worse than a moonscape.

I've been there too.  Horrendous.

Devon between Caldwell and Milwaukee, and Nagle from Gunnison to Narragansett. Lots of speeding cars. There's something about green space (forest preserve on Devon, golf course on Nagle) that makes people think they can speed. "Look! No driveways, so no cars will pull out and kill me! Let's speed!" Which ignores everyone else who wants to use the road.

Also, Chicago Ave east at Grand. Cars make the right turn onto Grand at speed (they do not slow down). Do not attempt without a mirror and quick stop brakes.

Those parts of Devon and Chicago Ave are what I call roads for the advanced bicyclist.

The Devon speedway is one of the worst. 

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