I can answer the question how long the flight would be.
When in Chicago the time is 10 pm, in Istanbul the time is 6 am.
Then, the flight from Chicago starts at 10 pm and it is 6 am in Istanbul.
The flight length is 5:00 pm - 6:00 am = 11 hours.
The length of the day depends on how the flight pat is designed and the time of year the travel takes on.