The South Shore Train is basically a commuter train with limited space for luggge especially during normal rush hours. During off peak hours most time luggage can stay with you on the seat as the train should be less crowded.
The Chicago station is at Randolph Street at Millennium park and is about a four block walk to Deaborn and the Blue Line to Ohare.
The coach USA bus will provide space for luggage under the bus and it will go to Ohare (Sometimes a bus change is required)
I would opt for the bus.

I'm assuming you mean you are having someone drive you to Michigan City to pick up either the train or the bus.

As the above poster mentioned, the South Shore is not meant for this type of purpose. The NICTD doesn't encourage even overnight parking and it is at your own risk.

I would also think that a vehicle left unattended for a lengthy amount of time anywhere would be considered abandoned and be towed away.

Agree that the bus is your best option IF you are going to have someone drive you there to meet it and pick you up.

Thanks for the replies. Yes, we have someone able to take us to Michigan City which seemed the most convenient drop off/pick up location.

Thanks for the info about the South Shore train. I'll keep that in mind for a convenient way to get to Chicago from that area of Michigan. Deborah

Also that train line is notorious for delays. I work with many people who live in that area and they drive further to take a different line than that one because it is so unreliable.

bertaron, the South Shore is notorious for delays and unreliable? I can see people saying that about Amtrak (which isn't a commuter train), though.

And what other train line is in this area? Are you talking about Metra way over by the state line?

BTW, I do know that the further west you get, the less likely you'll get a seat on the South Shore during the rush hour.

The most economical way is the South Shore. I think the one-way fare from MC is less than $8, and then the Blue Line would be another $2.25, or about $20 RT/person.

I've seen many people bring luggage on board the SS, large luggage, with flight tags still attached. Getting a seat in either MC or at Millennium Station would not be a problem -- too far east in MC to be crowded, and Millennium is the end (or beginning) of the line. And all of the trains have overhead racks, including the new double-decker cars.

However, as joethekay says, Millennium Station is at Randolph and Michigan, and the nearest Blue Line is several blocks southwest at Dearborn and Washington. So you'd have to schlep the luggage up and out of MC and then over and down to the Blue Line.

CoachUSA would definitely be more convenient luggage-wise, but twice as expensive.

Another option regarding the South Shore...it begins at the South Bend airport; there is a fee for parking, but the 25 days shouldn't be a problem. If you can get a free ride to the Michigan City Station, then you wouldn't have that cost. We took the SS into Chicago for a weekend stay (over a holiday weekend, not during commuter hours) with luggage and it was no problem at all.