Cheap flights from Chicago to Oklahoma from $57

The cheapest month to fly to Oklahoma from Chicago is in October. Flight prices, which tend to average around $68, are often lower during this time because this is during the off-season. If you are unable to visit Oklahoma during the month of October, then departing from Chicago during the month February is also very affordable. Most momondo users find prices during this month for around $81.

The cheapest day to depart from Chicago to Oklahoma is on a Wednesday when prices can be found for as low as $338. Flights from Chicago to Oklahoma on a Monday will generally be more expensive and average around $552. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

Flying to Oklahoma from Chicago in the morning is the least expensive time of day to depart. momondo users have found prices as low as $377 when looking at flights departing in the morning. If you have a flexible travel schedule, then try to avoid flying in the evening when prices are $524 on average. Flights to Oklahoma from Chicago in the evening are generally more expensive because this time of day is more convenient for travelers’ schedules.

Fly from Chicago O'Hare Intl to Oklahoma City Will Rogers World for the best Chicago - Oklahoma flight prices

You are more likely to see cheaper flights to Oklahoma from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Oklahoma for around $406 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Oklahoma from Chicago for as low as $237 on momondo.

Southwest, Allegiant Air, and Delta are the most popular carriers operating from Chicago to Oklahoma

American Airlines, United Airlines and Southwest are the top three most popular airlines that fly to Oklahoma from Chicago according to our data. American Airlines is the first choice among our users, with 51% of people opting to fly with this airline when traveling to Oklahoma. Keep in mind that there are 4 different airlines that fly to Oklahoma on a routine basis, so you have a few additional options to choose from.

As of May 2026, there are 165 flights per day flying from Chicago to Oklahoma. The most common time of day flights depart is 4:00PM, with 44% of flights taking off in the afternoon.

1,155 flights are operational weekly from Chicago to Oklahoma as of May 2026. The most popular departure day for this route is Mon, with 15% of flights per week taking off on this day.