How much does it cost to get into Canada with a DUI? Depending on your past criminal history and convictions, it can be difficult to enter Canada and can be costly. A DUI can prevent you from entering Canada. Prior to seeking entry to Canada with a past criminal history or DUI typically requires filing for permission with Canadian border officials before you can enter. If you have past convictions in the United States and have questions about your ability to enter Canada, you should speak with a Canadian inadmissibility lawyer.