Long time lurker here. I have a birthday trip planned for Chicago July 9th-11th. We will be staying at The Acme. On the 10th we have everything planned, lunch at Topolobampo, dinner at 42 grams, and possibly a night cap at The Berkshire Room if we are up for it. The 9th is a little up in the air though.
We are looking for a place that has a variety of great desserts that we can sample after dinner. I don't think we are looking for anything specific in the dessert itself. In the past we have done the Tru dessert tasting and Hot Chocolate. We are pretty open on traveling far in the city if it's a worthwhile destination, but near our hotel can sway our decision a bit. We also haven't quite pinned down dinner (maybe Boka since we enjoyed The Lobby on our last visit...), so if you have a suggestion for a great place that also has great dessert options, I'd love to hear it. We don't have a set budget or a preference over dressy vs. casual.
Edit: we will be arriving in Chicago at 3pm so we will have plenty of time to make just about anything work. Also, we have tossed around the idea of early drinks at The Aviary then wandering to somewhere in that area on foot if someone has suggestions on that.