Have always flown into O'Hare but the bargain flights on Southwest have me reconsidering - what is the best way into the city, how long will it take and how much will it cost? thanks in advance

"Best" depends on your personal criteria, but the El's orange line goes straight from Midway into downtown. Last time I did it it took 35-40 minutes from Midway to Clark/Lake. I don't know exactly how much a single trip is, as we got the 3-day transit pass, but it's cheap.

If you've taken the blue line into the city from O'Hare, you'll find the orange line from Midway to be a bit smoother/quicker/more comfortable.

I'm planning the exact same trip in a few weeks. Use this excellent trip planner tool on the CTA website: http://www.transitchicago.com/travel...p_planner.aspx to enter your starting point and destination address. The trip from Midway to our hotel near Michigan Avenue on a Friday afternoon will be 45 minutes, 1 train change and cost $2.25 one way. They even provided exact walking directions once we come out from the train!

And that sounds even more complicated that it really is! I wouldn't do it any other way, unless I had a lot of luggage (which I never do, so not a problem )

$2.25, trains from both Midway to the Loop or O'Hare to the Loop.