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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Milwaukee north of Devon.

Congress from Michigan Ave. to the start of the Ike.

No kidding. Rode it once, but never again.

Dempster Street pretty much from Dodge in Evanston as far west as Des-Plaines. Years ago i saw, of all people, Randy Neufeld, riding on Dempster in Skokie and asked him what in the world he was doing. He explained that he had been on the street for just a block and was going to a store right where I saw him.

Peterson, maybe?

Good mention, that should get more attention there. I know it's illegal, but at times(mainly if I'm going to the Target near Rosehill Cemetery) I have biked on the sidewalk there. Luckily almost noone walks on the Peterson sidewalk, so I don't feel bad biking on that sidewalk. Caldwell should be mentioned as well(which Peterson becomes west of I-94 and also Cicero), since the traffic is just as heavy.

I know before the North Branch trail opened up, I would go on Forest Glen-Lansing-Leader-Leoti to get around Peterson and Caldwell. And minding the fact Caldwell/Leader didn't have a light, and that the closest light was Caldwell/Lenox, 2 blocks west. Thankfully the North Branch trail extension to Forest Glen Ave. is now open, and very soon it'll be further extended to Foster.

Devon. Most anything west of Ridge is awful but at least the traffic is slow-moving. West of McCormick it's another suburban death race like both Touhy and Petersen leading out to the xpwy.

Sheridan Rd. from Devon to Evanston is best avoided.

Irving Park Rd. pretty much entirely.

Luckily Chicago is a grid so most of these streets are easily avoided.

Where I do I start? I ride around downtown a lot.

Worst,

Ontario, Ohio, LaSalle, Orleans (north of Wacker to Chicago), Dearborn (from Kinzie to Chestnut), Clark (south of Walton), Fairbanks/Columbus, not a fan of Lake

Faves,

Wabash (all time favorite), Grand (some parts are congested, especially around Rush and Franklin),  Illinois, Wells (except Old Town during party hours), Franklin, Superior, Huron (except between Dearborn and Wells), Erie (some parts suck), Kinzie/North Water, Lower Wacker service road, St. Clair, McClurg Ct., Randolph, Washington. I'm sure there are more...

Funny -- I love doing the "gauntlet" on Dearborn from Kinzie to Chestnut. If you sprint you can catch every light. And there's a bike lane. 

Also, Grand is Grand, but watch out for the construction from Sacramento on west right now. Brutal with tons of gravel and very little space for bikes to squeeze through.

The Archer International Speedway.

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