Describe the part in your commute that gives you white knuckles, whether its a street or bridge you cross, or a section that alway has you crossing your fingers. For me , its when i turn onto Higgins and i make the sprint to Bessie Coleman Dr . Lots of traffic, trucks ,cabs and passenger vehicles, and seemingly not many people paying attention

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I feel the hardest part of a commute is when things suddenly happen unexpectedly in a area that is normally uneventfully quiet. There have been times when you can relax a bit and then YOW ! The tough sections you can brace for and hold onto your holy medal, but the unexpected stuff gets me.
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Been there enough times.

Northbound Elston at Ashland during the evening commute. Drivers cut across lanes to turn right on to Ashland without paying attention. I have yet to find a way to go through that intersection feeling safe.

Ditto—until they change that sea of asphalt and enforce a speed limit I will never feel safe there. By jumping the red light at Armitage (very carefully) I can usually get ahead of the cars and make it safely into the left lane so I can cross without being right-hooked by cars trying to get from Elston onto Ashland at Kennedy speed.

Double Ditto. That is just a mess. It sucks cause Elston is mostly safer than Milwaukee - but I avoid it because of that intersection and at Fullerton.

I too work in the NW burbs, and the worst is probably the part on Wolf road (Golf to Prairie Ave).  While it's only about 1/2 mile, it's still a fast 4-lane road.

Des plaines going north turning west onto kinzie.

It's a three way intersection with Milwaukee and the bike lane and intersection is set up for bikes to turn left onto milwaukee or to stay straight on desplaines.

If you're on a bike making a left it's generally assumed by traffic that you are going left onto Milwaukee but no one ever seems to be prepared for bikes to make the sharp left onto kinzie.

I've noticed this issue as well. I don't feel safe making that hard left for the reasons you describe, so I cross Kinzie, stop, and proceed west when Kinzie gets the green light.

I take Foster ave east to the LFP. Where Foster intersects with the ramp for the outer drive both eastbound traffic lanes can turn right onto the ramp. The far right lane is easy to avoid but the left lane can either go straight or turn right onto the ramp. This leaves a cyclist no safe place to be. Since the ramp goes from two lanes into one before it merges onto the outer drive all the cars try and drag race to get be first. I have tried riding in the middle of the lane only to get nearly run over by traffic racing to be first on the ramp. I have tried riding on the double yellow line but there is no easy way to get there, again the traffic seems to be going much faster there. 

I've found that if you take the left lane and stay on the left 1/3 of the lane it's not too bad.  I try to take it on a red at the traffic light just before the ramp or before the light if you're not going to get a red.  Oh,  I also don't try to move up if I get a red at the light so that I have a clear spot in traffic.

Ending the ride at work. I typically want to keep on going.

Heading north out of the loop, where Franklin turns into Orleans at Wacker up to Hubbard.  The Wacker intersection always has cars blocking the box (which is huge because Wacker is at least 5 lanes wide).  The bike lane also changes position; it is on the far right of the bridge over the river, but then shifts to the left to allow for parked cars next to the Mart, then shifts back to the right down the decline, and narrows considerably as it approaches the bus stop.

Heading into the loop, Wells south of Wacker.  The buffered bike lane north of Wacker is freshly paved.  South of Wacker, the lane disappears, the pavement is awful, and the el supports are right there.  It isn't dangerous, but the quick change in environment is eye opening and I am always more alert.

Also, the more I think about the 4 lane speedway that Clark is between Armitage and North, the angrier I get.  Clark is 2 lanes north of Armitage and south of North.  In between, it opens up and cars are traveling way to fast.  Those extra lanes need to disappear soon.  It isn't that bad for cyclists, but pedestrians have few opportunities to cross Clark to get into the park.

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