I celebrate your success with you! Sugaring on business travel requires a very different approach and skillset than used when staying local. Sugaring on the road is much more about an "impulse buying" strategy and you found that out in a rather delightful way.
However, you may want to consider one thing: Do not negotiate against yourself. You had her at $400. That's a decent rate for Chicago, especially on a business trip. Then you bid against yourself by increasing the offer to $600. Why? Ok, the additional $200 a night won't break your budget, but it was probably avoidable, leaving that extra $600 for other purposes. When she countered with $400 all you had to do was say something like: "I'd love to do that for you, if you can stay overnight with me."
My guess is she would have accepted right away. Why?
1. She would not be likely to have another SD scheduled after seeing you at 11:00 pm, so she had no monetary incentive to leave.
2. It's possible you saved her more than $100 a night in cash for her lodging and travel expenses (if she was staying in a local hotel herself), or she otherwise would be staying somewhere that is not safe or comfortable.
3. She could have asked for more than $400 on your overnight offer, but it probably would not have been an extra $200 - assuming she is not a pro, and I don't think she is.
Finally, a word of caution about security and safety. You did well here, but I hope you took reasonable precautions like leaving your wallet, car keys, laptop and jewelry in the hotel safe BEFORE she got the room. Overnights mean you will spend at least a few hours dead asleep. And she will have unrestricted access to anything in your room, including the hotel phone which could be used to order anything on your card, especially if she drugged you.
Again, congrats for the win! Love to hear these stories, because...
Life is good
The Cat 
On the negotiating, you're probably right, but the 300/400 discussion was about a one hour visit, and I thought 600 for overnight was such a low ball number anyway, it seemed fine.
On the security, your points are really well taken. Two things -- I did lock stuff away and -- as in most sugar relationships -- I didn't pay her until the morning. So, she wouldn't have bolted. But you are right about all the necessary precautions.
I appreciate the feedback. I was definitely lucky in a lot of ways here, some of them just basic good luck, some of them as in the "lucky is better than smart" kind of way.
