New City Familiarization Trip?

I may be moving several hundred miles across the US to a city I have only visited for the interview.  How does one make a good decision about moving in such a circumstance?

I have a family to move as well.  Chicago living is decidedly more urban than my current location; it would be a major lifestyle change for us.

Another firm I interviewed with had a realtor drive me around the major sites of another city as well as giving me a speedy tour of the suburbs where many of the firm's employees live.  The company sold me on the city as well as the opportunity, but the city isn't as "famous" as Chicago.

This Chicago firm has me sold on the opportunity, but the only bit of Chicago I saw was right near the Midway airport and the business district.  I wouldn't want to raise a family in either of those places.  The location seems to be a given, like "why would anyone NOT want to live in Chicago?"  I mentioned to the head hunter the week prior (and to three of the interviewers on the day of) that location was among my concerns without getting any useful responses.  All of them are life-long Chicago residents.

Would you pack up the family and take a trip to the town at your own expense after you have an offer in hand?

Would a company, if they really desired a candidate, foot the bill for such a trip before the offer is accepted?  They had no qualms about flying me out for the interview on a full price, last minute fare.

Check with the company. Some

Check with the company. Some offer relocation services or may be able to refer one.
There are also several sites that offer these services for a nominal cost if not free.
Many companies are trying to control costs right now so they may not want to cover this expense. I would recommend taking a short trip out there with the family to look at the area once you have been able to narrow them down.
I face a similar situation where I may relocate for work. My wife and I decided that I would go out first to begin the job and begin the house hunting. Over the following several months, I will narrow down the areas we want to live and then bring the family
Out over a couple of weekends to look closer at houses and make a final decision.

Best of luck to you my friend.

I'd take a trip

I don't think I'd ever dream of moving my family to a distant location without letting them give the place the once-over.  Once, some years ago, I got an offer to go work in San Francisco (we live in Australia) and my wife was willing to move sight unseen, but we didn't have kids then and it was a much more fancy-free existence.  These days, I'd definitely want to get everyone's approval before taking the leap.

As to whether they'll pay for it, that comes down to how desirable a candidate you are and what the company's policies are.  If it's a senior position, or a very hard to fill technical position, and they *really* love you, you'll have more leverage, but some companies just never will (and others will fly you out at the drop of a hat).  You can certainly ask, though.  When you get the offer, just say that you need to make sure your family's on board with the move, and you'd like to bring them to Chicago to show them the city and how great it is (a little flattery never hurt).  Then just ask if the company is willing to defray that expense.  I would make it the last negotiation point -- if everything else is settled, and you'll take the offer if your family is happy with the location, then telling them that makes it far more likely that they'll be willing to say "yes" if they're on the fence.

There's a recent Career Tools cast on relocation that might be handy, too -- I don't recall it specifically dealing with fact-finding trips in detail, but it does talk a lot about how to "ask for more", and there's no doubt you'll be going through relocation if you take the job, so it's better to know what to negotiate for now.