Inevitably, any Chicago courier service will eventually face a customer who requests the possibility of billing the cost of the shipment to a third party. This practice is not one that is generally encouraged, simply because of the added risk that it presents to the courier company. There are always financial and legal obligations inherent in any business transaction, even one as simple as shipping something across a city or the country. And, when trying to bill the services to a third party, the issue can get much more complicated; something that most companies would prefer to avoid under most circumstances.
However, it would be inaccurate to say that there are no couriers which allow for third party billing options, as that is not the case at all. It is more accurate to say that this is not the most common of things, such a request may be denied, and that there are likely to be a strict set of rules and regulations that are attached to such an arrangement.
The most common case wherein a courier service in Chicago would be inclined to allow a third party billing request is when both of the parties involved in the transaction are account holders with the courier company. This request would usually be accepted, at least more often than those that are not under this situation, simply because the courier company has a relationship with each of the parties involved, and can be more likely to rely on there being no difficulties in the completion of the transaction. Also, a predetermined agreement by both parties in a given transaction which is shared with the courier company can also make this kind of a situation more acceptable to the delivery company.
You may also be able to find a courier service within the Chicago area that is willing to make a delivery on a COD basis. This isn't a service that is going to be offered to someone trying to make a single shipment with a delivery company, but rather a special option which might be made available to long term account holders. The reason for this is that if a client had established credit with a courier and the COD was not accepted or the shipment was declined, then they still have a guaranteed source of payment for their service, and like any other company in any area of business, the delivery company you are using is going to first need to ensure their own profitability and safety in every transaction.