When you reserve hired cars in Chicago, you are generally allowed to drive the car to nearby countries. However, if you plan on crossing the border with a Chicago car rental, keep in mind that you will need to provide additional documentation to your rental car company, like a passport or a passport card, as well as a government-issued driving license. Travelers driving to Canada with a car rental from Chicago will need to have a non-resident insurance card, while travelers headed to Mexico must obtain Mexican automobile liability insurance. Both of these can be obtained through most major car rental companies. If you plan on driving your Chicago rental car to a different country, make sure to let your rental car company know about your plans ahead of time.