Cheap flights from Chicago to Oklahoma from $110

The cheapest month to fly to Oklahoma from Chicago is in January. Flight prices, which tend to average around $356, are often lower during this time because this is during the off-season. If you are unable to visit Oklahoma during the month of January, then departing from Chicago during the month April is also very affordable. Most momondo users find prices during this month for around $371.

The cheapest day to depart from Chicago to Oklahoma is on a Wednesday when prices can be found for as low as $357. Flights from Chicago to Oklahoma on a Monday will generally be more expensive and average around $545. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

Flying to Oklahoma from Chicago at noon is the least expensive time of day to depart. momondo users have found prices as low as $377 when looking at flights departing at noon. If you have a flexible travel schedule, then try to avoid flying in the evening when prices are $525 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 Midway to Tulsa 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 $414 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 $277 on momondo.

There are 4 cabin classes available to choose from on Chicago to Oklahoma flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

United Airlines, Southwest, and Delta are the most popular carriers operating from Chicago to Oklahoma

United Airlines, American Airlines and Southwest are the top three most popular airlines that fly to Oklahoma from Chicago according to our data. United Airlines is the first choice among our users, with 48% 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 September 2026, there are 55 flights per day flying from Chicago to Oklahoma. The most common time of day flights depart is 4:00PM, with 45% of flights taking off in the afternoon.

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