Remitting hotel tax for direct STR stays

[Seb Ko]

Hi does anyone have experience with providing direct STR stays (so not through Airbnb or VRBO) and charging, collecting, and remitting the local Chicago hotel tax? What does that process look like? How often are remittances, where does one remit, etc?

[Henry Lazerow]

Most hosts in Chicago just pocket the full funds from direct booking, you would be in the very very small majority if actually paid city taxes on it. I just do all my bookings over airbnb, its too risky to go direct as the guests aren't covered by airbnb insurance. I have had to file claims with airbnb insurance twice and both times airbnb quickly paid out in full. It's worth just sticking in the app. I heard lots of scammers also trying to go off the app and then they say now need to evict me which takes 6-8 months in Chicago.