In all likelihood, if we play Chicago, it would be in the ECF, after they have already beaten Miami. So, we wouldn't have to play both, just Chicago.
The Celtics are most likely going to finish either 6th or 7th. Chicago is likely to finish 5th (I just don't see Atlanta finishing ahead of them). This means Chicago would play Miami in the second round, not Boston. Unless people think the Celtics are going to finish 8th, which I highly doubt.
I think our chances of beating Chicago pretty much come down whether or not Rose plays (which he would probably have to, if they are going to beat Miami). If he does, I doubt we can beat them. If not, sure, but I don't think the opportunity would ever present itself.