@Christina328 - We have many listings around Chicagoland and for this reason, we use Vivint Smart Home systems(https://www.vivint.com/).
Why Vivint Smart Home?
- You can pass keycode and ask check-in between 9 PM to 12 AM (or any time before 11 AM) using door keycode.
- You can see who checked in from your Apple watch or phone or web by VA or later review it.
- If needed, hire VA and they will do open it remotely ( you can hire per check-in basis).
- Dynamically generate keycode for each guest.
- Many more
When get chance I will make a video on how I do it or PM for a demo.
Thanks,
Suresh
Superhost, Chicago, IL
NOTE: I am a reseller for Vivint Home System