At the time of writing, the lowest price for a round trip flight from Regina to Chicago is CAD $246. The flight schedule from Regina to Chicago varies by airline and day of the week, but on average, there are usually two flights per week. The best time to fly from Regina to Chicago is in early to mid-May. Most airlines offer the lowest fares during this time of year, which is before summer tourism season begins and the demand for flights increases. It also tends to be the time when the weather provides the most favourable conditions for a smooth journey. The frequency of flights from Regina to Chicago varies depending on the airline and the time of year. Most airlines offer several flights per day from Regina to Chicago during peak travel times, however, during off-peak times there may only be one or two flights per day. Yes, Canadian citizens need a valid visa or have ESTA (Electronic System for Travel Authorization) to travel from Canada to the United States. 1. United Airlines
2. WestJet
3. Air Canada
4. Sunwing Airlines
5. Delta Airlines A number of airlines offer non-stop flights from Regina International Airport (YQR) to Chicago O'Hare International Airport (ORD), including: Air Canada, Delta, American Airlines, United Airlines, and WestJet.
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