RE: How early do we need to be at the airport before flights now?
Also keep in mind that if you hit a peak business travel time (Sunday evening, Monday early morning, Friday evening), you should allow some extra time at O'Hare. But my recent experience with O'Hare is that security is moving fairly smoothly - the only airport where I've stood in line a long time lately has been Indianapolis. Wear shoes that slip on and off easily to speed things up (we always take ours off rather than risk setting off the metal detector) and have DH empty his pockets into a ziploc that you put in your purse or the diaper bag well before you get to the x-ray machine.
Use curbside check-in if you have bags to check since those lines tend to be shorter; if you do not have bags to check, check in online at home (depends on the airline, though). I don't think that checking in at home saves much time if you are checking bags curbside at the airport. Just don't go inside and leave DH alone with the bags to check curbside - they will also want to see you with your ID before issuing the boarding pass.
Keep in mind, too, that some airlines (like United) fly out of a couple of different terminals, so you may have to walk more than you expect, unless you call the airline ahead of time to get a gate assignment.
For me traveling alone, 1 hour is plenty of lead time. With DS in tow, I shoot for an hour and a half so that we have time to grab some food before boarding, or he can burn off a little steam. But I know O'Hare pretty darn well so don't waste much time moving through the airport there. If you don't go there often, 1.5-2 hours is probably reasonable in most conditions to give you time to get through security and figure out where you are going.
Single mom to
DS ("twice exceptional") - September 2002
DS - February 2006
DD - July 2009
DD - July 2009