According to Service Alberta, the licensing agency for Alberta, in order to obtain an Alberta driver’s license or identification card, you must provide proof (i.e. visa, permanent resident card etc.) that you are lawfully entitled to be in Canada and proof (3 party residential lease agreement, letter from Alberta based employer etc.) that you are an Alberta resident. A registry agent cannot issue your driver’s license or identification card unless they are satisfied that you are a legal resident of Alberta.

Service Alberta goes on to note that if:

• you are a new resident in Alberta, you must obtain an Alberta driver’s license within 90 days of moving to the province, regardless of whether you travel outside Alberta during those 90 days.
• you are working in Alberta but have your residence outside the province, you may continue to use the valid license from your home jurisdiction.
• you are visiting Alberta, you may use your valid license from your home jurisdiction as long as you have a legitimate residence there and do not take up residency in Alberta.
• you are visiting Alberta from outside Canada and using an International Driving Permit (IDP), you may drive in Alberta for up to 12 months using the IDP in conjunction with your valid home jurisdiction license.
• you are staying in Alberta as a full time student or you are working here as part of a co-op program of study, you may use your valid driver’s license from your home jurisdiction.

These guidelines say that if you work in Alberta but have residence outside of the province you may use your home driver's license however since you have a house in Calgary and are working and staying in Calgary 80 percent of the time we would suggest that you contact Service Alberta, an agency run by the government of Alberta, directly to find out about your specific situation. You really need to find out if they consider you a resident of Calgary or still a resident of Chicago, Illinois in the US.

If you do get a Alberta, Canada license then they state that a valid license from the United States can be exchanged for a Class 5, 6, or 7 when the applicant is presenting a valid license of equivalent class. All other classes requested would require testing and must provide applicable medical and vision screening. All applicants must present immigration and residency documentation and acceptable identification.

Since it says your US license will be exchanged it sounds as if you would have to hand over your Illinois driver's license however you should check if they keep it so you could exchange your Alberta license back for the US one if you needed to or if the license gets returned back to the IL licensing authority.

The Alberta government states that one must obtain Alberta registration if their vehicle has been located in Alberta past 183 days. To get Canadian insurance on your car in Alberta normally you would also be required you to have a Canadian driver's license as well so that they can rate you for insurance purposes.