It'll be tough to explain being away for so many hours to the SO.  Plus, guys may not be familiar with the area at all.  Hell, some guys get lost within Chicago itself.  For them to drive to a city they are not familiar is asking for trouble [even with GPS].

Would you drive from Chicago to Milwaukee to meet a provider you wanted to see?

She would have to be a kick ass provider!

It's not just the distance, time and unfamiliarity with Milwaukee.  What if something goes wrong, say you get into a traffic accident, one that might require an emergency room visit, or what if some unforseen event happens like your battery goes dead, a blizzard starts and you cannot drive or whatever?  Poop happens, especially when you don't want it to.  The gain simply is not worth the pain.  Too risky.  Game, set and match.

turn about is fair..would you drive from Milwaukee to see a client in Chicago?..

Only if I was passing thru

Not a chance.  Plenty to choose from in this area

Listen to some house music on Sirius radio on the way, pickup some good cheese in Racine, and enjoy an attractive woman that is a freak...yup.

Sure, If she had decent reviews.  In the NW burbs so going there is not much worse than going downtown Chicago.

no I would not. I feel the experience should be totally about pleasure inconvenience.

That'd be like a guy driving from Miami to Clearwater, or NYC to Stamford, or Boston to North Attleboro to see a provider. While it's all possible, shouldn't the destination be the other way around, in the world class city?

Doing it tomorrow...

For a few reasons.

A. I wouldn't really be able to explain a spur of the moment trip to wisconsin
B. Even if the provider is well respected I don't want to run the risk of a no show and wasting a fair amount of time.
C. Although it probably wont happen but what if my car broke down or got towed or something. Its one thing to break down somewhat close to my normal location but having to make calls asking people to help me out in millwaukee would be a reach.


If I had a more "independent" lifestyle it would appeal more to me but for my current situation it would be way too risky for the reward

I second that brother!(e)

Absolutely.  I just did exactly that a couple of months ago.

I have in the past, yes.

Well with the ride...