Been to Cabo.
The Bad: Nice place as long as a hurricane doesn't come through there while you are there. Watch your wallet and don't drink the water unless it's bottled.
The Ugly: It's a 3rd world country, so, if you go out to town, it's not the cleanest of places in certain areas and be careful where you go.
The Good: It's right on the beach and there's a lot of things to do. Food is cheap (and tastes good too), drink is cheap, and there's a Ruths Chris there too.
I brought my family down there when I was still married and everyone had a good time. Funny story (to me at least), we just got there and we stopped to get a couple of drinks and when we got the bill, my wife freaked out because she thought it was 150 dollars and I had to explain to her that it was in pesos and was actually 15 dollars.
It is muggy down there, so, keep that in mind too if that's a big deal for you or your wife. Oh wait, you are from Chicago, so you guys know about muggy then.