I am planning to drive to Chicago (from Columbus, OH) for a short trip the week before Christmas. I hate to pay $30 a day to park a car that I don’t intend to use while I’m there... I was thinking of driving to somewhere outside the city then taking a train in. Any suggestions on how to do this or opinions on whether or not it’s worth the hassle just to save a little $$$ ?

Any reason why you don't take the Amtrak from Columbus to Chicago? Since you won't be needing the car while you are there?

That sounds like a real hassle. I'd just drive around and look for a free spot.
It may take a while, but not as long as commuting by train. Also, you'll be coming from the south, and southern suburbs or southside train stations can be in bad neighborhoods.

If street parking, check the overnight ban that went into effect Dec 1 ($115 tow + ticket)

Another alternative to the hotels that charge $30/night for parking would be a public parking garage or lot. Not sure where exactly you are staying but there are several public parking garages and outdoor lots in the downtown area which charge $15-$20 night. Still expensive, but cheaper than the hotel. If parking on the street, you will probably have to move your car several times throughout uyour trip or keep feeding parking meters which would be unrealistic. Watch out too if you are street parking in a neighborhood, many including mine, are zoned so that residents of that neighborhood only can park on the street with a sticker indicating that zone numeber. They always ticket for this too. I agree that parking outside the city and taking hte train in may be unrealistic. I think though I am not positive many of the CTA park and ride stations have a 24 hr. time limit on parking. The only thing I could think of would be to park maybe at the airport and ride in. Though airport parking probably isn't that much cheaper either.

I really appreciate everyone's advice, but I've decided to fly... It's cheaper for my family of 3 to fly to Chicago than it is to drive there and park. It's also only a 45 minute flight. Thanks again for everone's advice, though.