You would take the Purple line to Howard, where you would transfer to the Red line (the train is usually waiting for you) then transfer at State/Lake to the Orange line.It s hard to say if it will be safe. They do have security at the stations. I have noticed that it s ok up on the platform; you get into trouble when you go downstairs into the station. Mostly, you will be on top of the platforms. Once you re on the train, don t be afraid to walk to the first car and sit in the front if someone is harrasing you.I once got out of the train and quickly got onto the next car, leaving my looney looking daggers at me from the station as the train pulled away with me on it!!
it s possible, according to googlemaps.com and tripsweb.rtachicago.com. google maps says to walk to sherman noyes and get on the N201 bus to the howard train station. Then take the red line to roosevelt where you would transfer to the prange line, you take this all the way to midway. Or tripsweb says to get to howard via the purple line but the train wouldn t arrive until 6:30, there are several purple line stops that go past the northwestern campus, you would then do the same thing as if you used the bus.I personally would not approve of this because midway is located on the southside, to get there on public transportation you would have to go through some bad parts (back of the yards=scary!!) and weird people would be getting on the train. Not even rogers park by the train station is very safe at the time. So, no you couldn t take the purple line if you want to leave at 4am, if you waited until around 5:30 you could take the purple to the red to the orange, and tripsweb.rtachicago.com says that you would get to midway before 7am.
I take the Blue Line to the Orange Line every other day at 5am.Its pretty safe, same ol smelly bums around.