Hi @Darrell-Looney112 ,
This sounds like a booking policy issue to me. To fix this, make sure that your Chicago properties are using a booking policy that includes the correct rental contract. If they are set to "Always Use My Default Rental Contract", make sure that you have a rental contract that's currently set as the default.
Sometimes our users will archive a rental contract that is still in use or that is the default contract. This will cause issues in the checkout page, as you are seeing.