Get Hamilton tickets at face value. I saw Hamilton recently. It was fantastic. I recommend listening to the soundtrack and reading the Hamilton book by Ron Chernow in advance. Both are available at the Chicago Public Library.
Anyway I purchased my tickets, at face value, at the first pre-sale in June 2016 through American Express.
A friend decided to go and had been shopping Ticketmaster online for a while and the lowest priced orchestra seat ticket was $497 (sold directly by the venue) or more (resales by scalpers online through Ticketmaster). At the last minute they just went to the box office on a Monday the day before the show. There are no lines on Mondays because there are no shows. My friend was able to purchase an orchestra ticket for $180.
A quick check shows that the Venue (not scalpers) is selling those seats for $497. So if you’re downtown stop by the box office and give it a try. It may be a dirty little secret that you can get great seats at greatly reduced prices at the last minute directly from the box office. Of course YMMV. Good luck! You can also try to get $10 tickets daily How to enter the Hamilton Digital Lottery.