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Surprisingly, taking the LFP to Diversey doesn't seem to take any more time than getting off at Randolph and taking Milwaukee. Google shows the LFP route being a greater distance but about the same travel time as all-streets. It is kind of a slog with a good headwind, though!
I don't know how much winter cycling you do, but as the weather deteriorates you will want to get off the lakefront going north. That wind is brutal. Lucky you have made friends with Metra.
I ride in whatever the weather happens to be, though with this commute and really crappy weather I may just resort to the train both ways for the long leg. I've ridden up and down the LFP in winter plenty, and as long as the path is not icy I'm fine with it. Headwinds suck no matter what the weather! :)
My problem is, no matter which direction I bike in, the headwind always follows me...
No, the schedule indicated bikes are allowed and I've had no issues with my bike, likely since it's outbound in the morning. I ride in the first car, since my stop is a flag stop. That's the most crowded car (mostly with people going to the University of Chicago) but even that is fine. It works well for me, since I can make the 7:43 train without getting up any earlier than 6:00, and if I don't make that one there is another one half an hour later.
Fortunately, my office is just east of Cottage Grove and I only have to ride on 103rd for a block and a half. My boss said the other day it took him onlt 45 minutes to get from State/Lake to our office via the Red Line and the 106 bus, so that seems like a good option that takes less time than I expected.
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