Even those that have been utilizing a Chicago courier service for a long time might occasionally find a question or issue that they have not already thought to address that they aren't aware of the answer to. Whether or not it is possible for a shipment to be billed to a third party is one of the questions that can arise from time to time. Since this would be up to the sole discretion of the actual courier this is not a simple question to answer. This is not a very common practice. It is safe to say that there are a variety of reasons that this type of request would be denied.
Most couriers would be lead to simply say no out of hand to all requests of this nature for ethical, financial and legal concerns associated with the practice. It would not be taking a full examination of the question to just dismiss this as something that never happens since there are some cases when this practice is allowed. It isn't very often that this happens however. There are specific and predetermined circumstances that this is allowed in with most cases.
Remembering that it will be up to the Chicago courier service to make the determination to whether or not billing a third party would be appropriate or allowed is important. There may be some circumstances or policies put in place that allow it. In a situation where both the receiving and shipping client have held accounts and been clients for a long with the courier company is one of these times. The companies might have made the courier aware of the mutual billing agreement between them and if this has been requested on the behalf of one or both of the parties then the company might allow it. In this case the practice might be allowed.
A COD situation where the recipient of the shipment or delivery is charged is another situation that third party billing could be allowed by a Chicago courier service. In order to ensure they still have a guaranteed payment in the event that the payment for COD does not appear on delivery most will only provide this service for high credit account holders of the courier company. Usually this practice is only done when the companies see that there isn't going to be any possibility for legal or financial liability for third party billing on their part for allowing the practice.