delete

I also feel like my re engagement game the next day when I text her sucks, or whatever it is. I had a good conversation going about chicago... But then, when that conversation died and I tried to just ask her a question nothing out of her...

You're not having a very interesting conversation mate. You've got a decent amount of conversational directions to take it in but you're remaining pretty cut 'n dry, e.g. boring. You got to make a woman feel emotions. Read the "Best Of" text game threads there's plenty in there to learn from. 

Is there anything I can do to get her to reply to come out with me tonight?

Sure, but it would require me to babysit you and your phone and I'm just not available to do that.