I would go to Alinea too.
Earlier this year, we really, really wanted to go to Alinea for my birthday, but the price was an issue. We went, and got the smaller menu (they now offer only one), and only ordered one glass of wine between the two of us. The serving staff was as nice as could be throughout; there was not even the slightest whiff of attitude (unlike what you describe at Trotter's, which I hope happened a long time ago and wouldn't happen again today). And the meal was a wonderful experience I will remember forever, with food that was amazingly delicious as well as FUN.
According to their website, dinner at Alinea is $185. If you consider wine an essential part of a dinner, you're going to pay considerably more for the privilege. But if you can limit your alcoholic intake during the meal - perhaps have just a glass each, or maybe instead open a bottle at home before leaving for dinner - you should be able to eat there for somewhere around $500 for the two of you. Granted, that's not inexpensive. But it's also not $700. If that makes the difference between going and not going, go for it!
If, OTOH, you decide not to spend that much, there are other options. For example, Everest has a fixed pre-theater menu, $55 for 3 courses for seatings at 5:00/5:30.
If you decide to go for a more casual fine dining place, in the same category as Blackbird, graham elliot, Perennial, Naha, etc, you can have a very nice dinner for under $100 each at such places. In fact, some of the very best meals I've had in the past few years have been at similar places which happen to be in the suburbs:
Michael in Winnetka,
Inovasi in Lake Bluff, and
Tallgrass in Lockport. Michael and Inovasi are both one block from Metra stops with train service back to the city well into the evening hours. And of the three, Inovasi is quite a bargain - in fact, a downright steal! (Even the wine prices there are moderate.) I've been there twice now; the first time we ordered three courses each and, including wine/tax/tip, it came to $50 per person. The second time we ordered four courses each and it turned out to be too much food, but the total still came out to only $66/pp inclusive.