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?
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.
I have experience handling this in Michigan with my short-term rental. We simply include the tax on the invoice sent to guests, which makes it easier to track and ensures we're covered for tax purposes at the end of the year.
For Chicago, I'd recommend checking directly with the city's tax office or a CPA, but generally, you'll need to register with the city, collect the hotel tax from guests, and remit it on a regular schedule (likely monthly or quarterly). The City of Chicago website should have details on where and how to remit. A CPA familiar with local STR regulations can definitely help make sure you're set up correctly!
I'm in the Tampa area and mainly had mine in the Pinellas County area. We also had a transient tax and municipality as well. I used Hostify and you can work it into the management system to figure and charge all of that for you.
I'm in the Tampa area and mainly had mine in the Pinellas County area. We also had a transient tax and municipality as well. I used Hostify and you can work it into the management system to figure and charge all of that for you.
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.