Tipping your courier can be a difficult thing sometimes. First of all, we seem to live in a society where we, in North America at least, have put a pressure on ourselves to tip everyone all the time. Where there are now, due to current employment models, situations where this sort of behavior might be appropriate and encouraged, the waters are much muddier when it comes to tipping the driver from your Chicago delivery service. To begin with, some courier companies will have a blanket policy that prevents their employees from being allowed to accept tips or gratuities of any kind. This is something that you should definitely research before you try to tip your driver. You could either end up embarrassing them if they don't accept the tip or if they do and you mention it to someone else at the company you could end up getting them in trouble, so it's a good policy to check on the courier companies tipping policy before you try and give your driver a tip.
Now, if your Chicago courier service driver is allowed to accept tips, the first thing that you might have to consider is how often to tip them. If you have a delivery driver who comes buy every single day, it might get a little cost prohibitive to offer them a tip every single day. However, in that situation perhaps providing them with a Christmas or yearend bonus as a kind of tip might be appropriate and likely quite appreciated. Another option is to tip when your driver makes any gesture that you could consider as exceptional customer service.
If your Chicago courier service only sends a driver buy once a week or less however, and especially if they are always polite and provide good service, then a regular tip might be a good idea. Many people in this country that work at a variety of professions are compensated fairly but still are not making the kinds of money that a business owner might be, and it is always a nice gesture to help share the profits of your business with the support people who help make it all possible. After all, if your driver wasn't competent and reliable and your deliveries never arrived on time or at the right destination, your profits would likely sink very quickly, so it is nice to give something back to a good driver.