To a Mainer, the idea of going to a fancy joint and dropping $50+ on a lobster is a joke. No one here would do that. Instead, we'd go to a place like McLaughlin's and pick up a couple of bugs and make 'em ourselves. Earlier this summer we got three chicken lobsters (1 to 1.25 lbs) for $20, and they were excellent. And they're incredibly easy to cook; even a complete putz in the kitchen like me couldn't ruin 'em. If we had to go out for them, we'd go to a lobter pound, which is basically a shack near the ocean with a whole lot of lobsters in a tank, just off the boat. You can get a lobster dinner there for ~$20-$25. Fancy it ain't.
Of course, since you're not in Maine, the latter is not an option. My suggestion in that event would be to have some frozen lobster tails sent out. Cheaper than shipping a whole live lobster, and since the tail is where most of the good stuff is anyway, you won't miss out on much. Yeah, it will be frozen, but I don't think the quality will diminish that much compared to the price differential.
The thing with the live lobsters in a tank is that they'll have had their claws banded together to prevent them from using them to attack one another. When the claws are banded for an extended period (and those in a tank in the midwest will likely spend more time with their claws banded than they will here), the meat inside atrophies, meaning there's a good chance you'll get a lobster with a big, mostly hollow claw. Then you'll feel ripped off.