Ok, so we went to Oak Mill Bakery, Bennison's Bakery, Jarosch Bakery and Molly's.
Here's what we found. Oak Mill charged $25 to do the tasting. This was the first tasting we went on and we didn't know any better, so we paid it. We tried their vanilla, chocolate, red velvet and carrot cakes, pre-frosted with their chocolate and vanilla butter cream frostings and their cream cheese frostings. It was all adequate...not great. A little dry. Their carrot cake was more spice cake than carrot. I've had other stuff from Oak Mill that's been very good, though. They charged $2.75 for the red velvet and carrot and $2.25 for the chocolate and vanilla and there was no discount for buying in quantity. The cupcakes were slightly larger than the standard size, but not huge. We also wanted a cake to go on top of our cupcake stand, so could cut a cake at our reception. They wanted $75 for a 9" chocolate cake with mousse filling and chocolate ganache over it, and a few flower decorations. Plus $65 to deliver it to Grayslake. About $590, total, including tax for 175 cupcakes and a 9" cake.
On to Bennison's. Free tasting. They gave us unfrosted chocolate, vanilla, red velvet and carrot cake cupcakes and little sample cups of chocolate and vanilla butter cream, fudge, whipped cream and cream cheese frosting and we could mix and match however we wanted. Everything was very good, especially the fudge frosting. The chocolate and vanilla cupcakes were only .95 each, no matter what frosting you got, and were the standard size. The red velvet and carrot, which were larger (but could be made smaller), were $2.96 each, or $1.51 if they did the smaller size. There was a 20% discount once you hit a certain amount. The woman who helped us was going to get back to us on what that quota was, as well as letting us know what the delivery charge would be. The 9" cake would have been $15 (!) and any of their fruit/custard fillings would have been $3, except for the fresh strawberries, which would have added $7. Decorating was included in that price. Because there were some unknowns (the woman wasn't sure about the delivery charge, either), they didn't give us an official quote, just wrote down the prices.
Then I went to Jarosch. When I set up the appointment, all I asked for was a "tasting", the same as what I asked for at all the other places. I told them I was interested in chocolate, vanilla, red velvet and carrot cupcakes. When I got there, they gave me and my mom each a slice of three-layer cake with a chocolate, red velvet and carrot layer. There was vanilla butter cream over and in-between each layer, except the carrot layer, which had cream cheese on it. The woman who presented all of this to us gave us a cake box and said, "and here's the rest of your cake for you to take home!" We thought that was really generous of them. They left us alone with our cake and their portfolio. Again, it was adequate, not great. Their chocolate frosting is a slightly chocolate-y light brown version of the vanilla butter cream- not nearly the amount of chocolate-y-ness I require. After a few minutes, another woman came over and we talked about what we wanted. She got to the end and asked if we had any questions. I said I just wanted a copy of a quote so we could look at it and make a decision. She said she'd have to talk to the head decorator and see what they'd charge for all of it and then she'd type it up. We were in no hurry, so we waited for it. Then she came back and presented the quote. $4.75 for the red velvet and carrot and $4.25 for the chocolate and vanilla.

$65 for the 9" cake on top. $75 for delivery. Almost $1000 for 175 cupcakes and a 9" cake.
Then she says, "now all I need from you is a deposit."
"Um, we were just here to taste today- I still have to talk to my in-laws who are paying for this."
"Oh, so you're not buying today?"
"No, I'm sorry for the misunderstanding, but I just requested a tasting and no one asked me what my intentions were."
She handled it well, but just the presumption that I was going to walk in there and make a decision on the spot, let alone plop down a deposit for $1000 worth of baked goods, was ridiculous. Not to mention when she was writing down our order, she wrote down "vanilla butter cream on all" and I had to correct her, that we wanted cream cheese frosting on the carrot cake and red velvet. The assumption that we'd want butter cream on red velvet I can forgive....but any bakery that defaults to butter cream on carrot cake loses some major points with me.
In trying to get in for a tasting at Molly's, there was some miscommunications. The person who handles the tastings is only there in the mornings and when I called to get her information, no one bothered to mention this to me, nor that the next day was her day off. I was trying to coordinate the tasting with a dinner thing I had going on in the neighborhood later that week, and the coordinator didn't get back to me in time ("someone must not have printed out your email, so it didn't get put into her to do pile") so I was ready to scrap the whole thing and go with Bennison's. I decided we should go for an unofficial tasting this past Saturday morning. We got in there and got our four standard cupcakes. It was pretty busy when we got there, so we assumed that we wouldn't be able to talk to anyone. My in-laws loved the cupcakes, though, especially the cream cheese frosting. It's just how we like it- more like sweetened cream cheese than sugar with a little cream cheese added. After a little while, it started to clear out and we were able to talk with the girls behind the counter. None of them were the person who handles the scheduling of the tastings, but they were able to give us some good information. We're not sure if they deliver to Grayslake, though- that's the only potential problem. My matron of honor, who lives in Rogers Park, may be able to pick them all up the morning of the wedding. They seem to do a pretty good job packing them up, so as long as it's either not too warm that day or they can keep their car cool enough, we shouldn't have a problem with them melting. Anyway, like I said above, their cupcakes are $1.80 each for the regular size, non-filled ones and they charge $35 for a 9" cake. The other downside is that they don't really specialize in cake decorating, to we may not get to do the decorations we want. We just want a simple cherry blossom decoration on the cake and a single cherry blossom on each cupcake, so we'll see. I'm going to email the coordinator this week and see if she can give me a real quote and if they can do the decoration. Either way, they're by far the best cupcakes we tried (seconded by Bennison's), so I'm willing sacrifice a little.
Oak Mill Bakery
(multiple locations, but this is the one we went to)
8012 N. Milwaukee Ave.
Niles, IL 60714
(847) 318-6400
Bennison's Bakery
1000 Davis Street
Evanston, IL 60201
(847) 328-9434
Jarosch Bakery
35 North Arlington Heights Road
Elk Grove Vlg, IL 60007-1480
(847) 437-1234