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I would also take Damen. I've never made it all the way to the Medical District, but most of what I've traveled has not slowed me down at all.
I've ridden the stretch of Damen past the United Center at all hours of the day/night--including at times so late at night/early in the morning I'd rather not admit. Outside of how absolutely horrible traffic can be if you end up hitting that stretch during an event at UC, it is a relatively safe area now (at least IMHO).
Generally, I'd go with #2.
I like Ravenswood-Wolcott-Damen down, for the most part. The North & Milw. intersection bites of course, but at 6:30am it should be fine. Heading back up @ 8pm it's a sh*tshow.
I can't say I agree with #3- I find Clark-Halsted south is pretty good too, if you can get the timing right. The giant overpass centered at Chicago is in terrible shape, so take the sidewalk over it.
I would think the event gridlock around the US would actually make Damen /safer/ than at certain mid-volume times.
My vote is Damen. Not even a contest IMO. (Unless your starting point makes the lakepath make more sense.)
I'm not sure how anyone can attempt to provide a useful answer without having a better idea of where the starting point is.
Do this commute every day, start near the Southport brown line stop to the medical district. For awhile I did Greenview-Fullerton-Ashland-Elston-Ogden-Paulina. Elston is great and you're really only on Ashland for 2 lights. I stopped due to the excessive speeding on Ogden, this would probably be even worse for you at the off hours.
I take Damen every day now. It can be a little slow with all of the lights through Bucktown, but it's still the best bike lane the entire way. I typically start to head East to Wood or Paulina on either Fulton or Warren. You can cut through the Rush hospital area on Paulina depending on how far south you need to get to (technically Paulina dead ends at Congress Parkway and starts back up on Harrison for cars).
Halsted is a decent option as well depending on where you start in Lakeview. I live further west so not worth it to do the backtracking.
As far as crime - I've never had any problems and on a bike you should be fine. We'll occasionally be notified of muggings and other crime in the area once every few months, but it's typically pedestrians very late at night.
I'd love to come up with a faster route though
I take Damen whenever I have to go to Rush from Lakeview.
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