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...
Cicero from Peterson to just north of Montrose. A death wish with narrow turns through viaducts and cars exiting the Edens expressway. Ended up on there by mistake years ago and the thought of it still gives me chills.
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.
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.
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
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.