I have just done something similar in Aus.
Started 10 Female Strains and One Male under light.
Planted outside in Coco when days length = about 12 hrs.
Plants directly seeded outside @12/12 will often continue in growth for weeks to a month for late strains.
Plants established under 24hrs light will turn almost immediately when taken outside @12/12.
Followed closely by Later strains in the next 1-2 weeks.
My point being it can be better to establish plants inside.
So they flower more in sync when planted outside @12/12.
Keep the Nutrient strength low until plants adjust, it can take some time.
Only increase strength if the roots have established in outside coco, you can still set seed either way!
Outside, pollination can be far more sporadic and hit and miss then the grower wants.
Put male on upwind side. You can also place flowering branches in bottles full of water to double up areas of concern.
This will give you at least the second day’s pollination in another location before the cut branch droops.
Keep in mind that shortening days and cooler weather will delay seed maturity to about 2 months from pollination.
I Left the Male 11 days after the first pollen release. The plants were from lightly or under-seeded < 30, to heavy > 100-1000 downwind.
I had to cover plants every night for a month to protect from frost or rain. Otherwise the plant would not mature good seed.
Chicago Day Length:
Might work for you, depending on situation in Chicago.
My guess is that you have no where outside to grow.
But just in case it helps.