Would you fly to Chicago, and then have relatives pick you up, and drive 5 hrs. to La Crosse, WI? This airfare would cost $250 for 3 people. Or would you drive the whole way to WI- 11 hrs, & stay in a hotel or bed/breakfast on the way and maybe on they way home? This also involves travelling with a 3 year old.

WI, need a little more info. If you're thinking of flying into Midway, its a LOT further than 5 hours from La Crosse.
You're thinking of having them drive from L.C. to pick you up? Thats a good 10 hour round trip for them to O'hare and more like 12+ round trip L.C. to Midway. Either way, I'd personally never ask anyone to "pick me up" if its that far of a drive.
Can you fly into Madison and pick up a rental car?

Consider flying into Madison, Minneapolis, or even Milwaukee. If you must fly into Chicago, check into Midwest Express flights to LaCrosse, Appleton, Oshkosh, etc. Any of those options are better than what you propose.

My parents are staying in a hotel in Chicago, so they would already be there
to pick us up. We could fly into Madison; that would be $450 for 3 people. According to Yahoo, Midway airport to La Crosse is 4 hrs. 40 minutes.

Yahoo is full of ....!

Yes, it may be 4.5 hours if you have great traffic, but then it can sometimes take 2 hours just to get out of Chicago!

Definitely consider flying into Madison or even Minneapolis.

But saying that, if the drive is ONLY 11 hours (notice how our priorities have changed since 9/11) you probably aren't saving that much time by flying. Where are you coming from?

The only thing I would really advise is to avoid Midway. If you fly into Chicago fly into O'Hare - at least that way you are on the North West side of Chicago and usually you will not have any traffic problems heading out of town.

No way is La Crosse 4.5 hours from Midway. My family has a place just south of L.C. and I drive to and from Mke many times a year. It takes @ 4 hours just to do that.
Anyway, whatever way you decide the La Crosse area is beautiful. If you've never been there before, you're in for a surprise. Be sure and take some time to explore the bluffs and coulees.

We are coming from Ohio...the drive to the airport here is 45 minutes, & we have to pay for parking. If we drive to WI, we have to drive past the airport anyway. Never been to La Crosse, nor to WI. We can stay halfway at a country inn in Indiana for $60 + tax, which includes indoor pool, hot tub, & breakfast.

Are you doing this in the next few weeks?Because if you are I think that the drive would be gorgeous with the fall colors and the western part of Wisconsin is fabulous in the fall.If you could, I think that I would either fly into MSP airport and rent car from there or see if you could fly into ORD and then rent car from there. Give us some more info as I am sure many people could help you. Wisconsin is a great place to visit!

Air time is 4.5 hrs. to Madison, with connection in Chicago.

Given the extra info you have provided, I would drive

I used to live in Wisconsin (Madison). I have driven a similar route (except not on to LaCrosse) a couple of times between there and NC. I would advise flying into MN or Madison as others suggested or driving. Unless things have changed though, it may be hard to find direct flights to Madison. Personally, I would probably drive and break up the trip as you were thinking.

We are leaning toward driving the whole way with a stop halfway. If we decide to fly, it would be to OHare. Thanks for the tips to avoid Midway.

What seems to have been overlooked in all these answers is the "three year old." If he/she is a reasonably good traveller, then by all means....make the drive. And consider...you mentioned the airport is a 45-minute drive from you...plus, you have to be there 1-2 hours before flight time right? Then...you could have a flight delay. And you're still left...with a five hour drive on the other end....Contrast that with getting in your car (with a hopefully cooperative and peaceful toddler)...and probably having two thirds of that first day's drive done with about the time you'd be touching down in Chicago. (And if you flew into O'Hare, you'd still have to factor in another 3/4 to 1 hour before you even got out of there and underway.) Happy travels!

Excellent advice! Thanks.