How "doable" is it to take the CTA train from O'hare to Midway with luggage?
How far is the midway station from the airport.
I know the Ohare blueline station is right in the basement. How long approximatly is this ride?

Try this site. You can do a travel planner. It's the official CTA site:

http://www.transitchicago.com/

Have a great trip!

I had already checked out this website---what confuses me is that the cta page says that you need to take a bus from midway to the train station, but midway airport says it is easy acessible from the station via an escalator and moving walkway. How far away is the station from the airport?

Go back and look at the train map. I believe the best transfer station is the Clark station. Do a planner from O'Hare to the Clark station and then do Clark station to Midway. Add about 10-15 minutes for the transfer and at least you will get the time needed for such a journey. It has been some time since I flew into Midway, but I would guess it would take you about the same time as O'Hare to walk from the station to the check-in counters.
Hope this helps and have a great trip!

A huge pain! It is a horrible walk to the train station at Midway(a mile maybe!) Then, you would have to go into the city, change trains, then out to O'hare. The trip into the city would take about 2 minutes, the trip out to O'hare would be about 45 minutes.

A cab wouldn't be cheap ($35-$45?), but sooo much easier!

The trip from Midway to downtown is about 25 minutes (not 2, obviously...sorry about the typo!)

There is an O'Hare-to-Midway shuttle called Omega that might be a better choice. Go to
http://www.ohare.com/midway/ground_transport/ground_transportation_shuttles.shtm

for more info.
If you do take the CTA, allow 2 hours for the trip.