Here's what it's like being a cyclist on the streets of Chicago: I nearly got hit BAD yesterday and forgot to post about it until just now.

Riding in a bike lane, to my left is a long line of cars stuck in traffic. I am always very cautious about this scenario so I'm not going top speed, thankfully. As I pass a Burger King, a car squeezes through a tiny gap in the cars that I didn't even think was big enough and nearly nails me. His front bumper stopped literally 4 inches or less from my wheel.

I am only on this road for like 6 blocks but I really gotta find another option, so many of my close calls are on this road. Why is this tiny stretch so bad? It's filled with car-oriented businesses with drive throughs and huge parking lots and multiple curb cuts.

The land use you build determines how people interact in and with it.

I just looked at a map and remembered why I ride this route. There are train tracks that only have underpasses on major arterials, so I'm stuck riding them to get from one side to the other. There's a slightly better boulevard that goes under them, but then after I get west of it I'm stuck trying to get north with no streets that have a controlled intersection with the arterial I'm trying to avoid, so I can't cross it safely.

For the locals/curious, here's a map.

Green to light blue (a contraflow bike lane) to royal blue is my old route.

Royal blue is my current route.
Red Xs are where I've had close calls or crashes.

Yellow Xs are uncontrolled intersections - no light or stop signs for traffic going E-W.

Green is the boulevard option but once you pass the state route (Cicero) there's no way to get north.

The dark purple is what I was hoping was an option until I saw it doesn't cross the train tracks.

@kaz That whole area from Cicero to Pulaski between the tracks is a mess. I'm glad they added the contraflow lane on Roscoe, but that's north of you. And that west Diversey segment is horrible for all the reasons you mentioned. I hate riding it.
@kaz There's a weird tunnel crossing on I think Wellington...but only one track (the east one).
@madopal Oh interesting, I may go check that out. Wellington would be ideal if it crossed the tracks because there's a light at Cicero too.
@kaz Riding this week, was going to share my route. Roscoe now has a contraflow lane, so you can take that underneath the farthest west tracks. Also has a light at Cicero. After that, you can take Kostner to Wellington and over. On the way back, you have to do a jog off of Kostner at Belmont to next west street, but gets you back up to Roscoe.

@kaz Full route:
To city: Laramie->Roscoe->Kostner->Diversey (Wellington is 1 way west, but only a few blocks)->Hamlin->Cortland->Lawndale->606->Milwaukee

Back: Milwaukee->606->Lawndale->Cortland->Hamlin->Armitage->Avers->Wellington->Kostner->Belmont->Kenneth->Roscoe->Laramie

Obv any of these you could take Diversey or Wrightwood (not too bad further east) over to Milwaukee instead of taking the 606. I generally only do the way home because taking Milwaukee saves 5-7 minutes in the morning.

@madopal I have a friend who lives in Portage and sometimes takes Armitage all the way to Laramie, have you tried that? Feels like it wouldn't be better than my current route but he says it is. 🤔
@kaz I tried it a few times...Laramie and Armitage further west feel much like you were talking about (curb cutouts, etc). It is narrower and slightly less traveled than Belmont/Diversey, but I do prefer the side streets up here. Especially now that they added all the lanes in Cragin.
@madopal Yeah I guess I'm just resistant to Roscoe because it means going 0.7 mi further north than my house and 0.7 mi back south. Almost a mile and a half of extra riding!
@kaz Was wondering how far out of the way it was for you. Feel you on that, that's a lot of riding.