I have my first overnight in Chicago and im just a bit.nervous. I dont know the best way to enjoy the full time I will be with her. Any tips and advice? Should meet earlier than later?  We are getting dinner together though

If not, I don't know what to tell you, but assuming you have, just treat it the same way, but know it's a date where you are guaranteed to score. Don't put so much pressure on yourself, just have fun and treat her like a "real" woman and you will be just fine.

On second thought, I do have some advice for you if you've never been on a "real" date like this, simply hand the reins over to your date. She has likely done this a hundred times so let her take the lead this time. Just relax and go with the flow, she may even like "being in charge"

That's often a bit tricky. Overnights should be with someone you have met before and know that you click with.  

Start with a nice hotel, great dinner, and wine then relax and let the evening play out. If there is any connection you will have a great time, if not all the planning in the world will not improve anything.

Great answer!!!!!