Attending a law enforcement conference as a vendor in downtown Chicago, have to arrive on a Sunday and take the blue line from O'Hare to downtown with 2 large bags to display our wares at the conference.  I've taken this train once before mid-day, it was no worries at all, but I'm well familiar with Chicago.  

Thus....I have to option to:

1) fly in 6 hours earlier than needed and take the train downtown early, kill time downtown instead of with my family

2) fly in and take the train downtown on a Sunday night around 10pm.  

Is this train line safe late on a Sunday night or should I just go early?  I'm always unarmed when in Illinois.  Other states I usually travel with a firearm.

You'll be fine.  Blue line to/from O'Hare is chill 99% of the time.  

Very safe

Cool, you guys just save me a few more hours of time to spend with my family, thanks.

You'll be fine, just keep your eyes open and be aware of your surroundings. As xmikex said above, 99% of the time the blue line is chill, but "shit" does have a tendency to happen when you least expect it.

Edit: Didn't fully read your post and see that you'll only be on the north leg of the blue line. I've never traveled on that segment so i don't know how it is. The south leg of the line is PROBABLY where the "shit" would turn up, if it were going to.

This.

I worked the CTA reconstruction project for about 4 years or so.  Majority of that time at night all over Blue, Brown, and Red.  Saw a ton of bad and bizarre stuff.  Most of the crap happened in or around the stations and on the platforms.  South of downtown aka "The Loop" at night can be quite the adventure (especially the Red line).  It is starting to warm up here so there can be some spring fever.

Like anywhere - keep your SA up, move with a purpose, watch what you say, etc. Basically, don't look like easy prey.  I don't recommend the Wolf Stare 'cause sometimes that sets 'em off.  Pepper spray with restrictions and max blade length is 3".

Flip side if you get some down time is that there is a ton of stuff to do downtown, river walk, lake front, sports, beautiful wimmenz , etc and overall I think the city is much cleaner than it used to be.

By Chitcagostan standards, the run from Ohare to the Loop is safe.  Just stay away from the obvious suspects and dont put yourself in "take me!" positions.

Why not just grab a cab so you don't have to lug the bags?

$2.25 for a ride on the beautiful L or $30 for a ride in curry stained cab...

blue line is gtg. op sec 24/7 365

I'd also add that a cab will PROBABLY take longer due to trafffic, etc.

If your destination is anywhere near a blue line stop, take the blue line.

Do not, under any circumstances, play with/have ear phones on with your blackberry/i-pod/i-whatever unless abso-f-ing necessary.   Lots of snatch and grabs (one bastard tossed an old lady down the stairs and killed her trying to get away after a snatch).

I have found the Brown-line to be the most civil.  The lines south and directly west of the loop are sketchy at night (personal experience).

Try sitting in the first train where the conductor is.

Not sure what the "wolf look" is, but keep your eyes up.

You'll be fine.

Common sense still applies.