Cheap flights from Oklahoma City to Chicago from $65

The month of September is, on average, the cheapest month to fly to Chicago from Oklahoma City, with most prices found around $264. If you’re not able to fly to Chicago in September, then January is your next best option. Flight prices from Oklahoma City to Chicago during January average around $322.

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $528. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Oklahoma City to Chicago for around $748.

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Oklahoma City to Chicago during this time can be as low as $522. In contrast, the most expensive time of day to depart to Chicago is in the evening when prices are around $909.

Fly from Oklahoma City Will Rogers World to Chicago Midway for the best Oklahoma City Will Rogers World - Chicago flight prices

You are more likely to see cheaper flights to Chicago from Oklahoma City when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $366 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Oklahoma City for as low as $244 on momondo.

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

No. A direct flight is the cheapest option for a flight between Oklahoma City to Chicago.

As of March 2026, prices for Oklahoma City to Chicago flights are approximately 234% more expensive when compared to flights at the same time last year.

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

American Airlines, United Airlines and Southwest are the top three most popular airlines that fly to Chicago from Oklahoma City according to our data. American Airlines is the first choice among our users, with 45% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 4 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

17 flights are operational daily from Oklahoma City to Chicago as of March 2026. The most popular departure time for this route is 1:00PM, with 50% of flights per day taking off in the afternoon.

As of March 2026, 124 flights take off from Oklahoma City and land in Chicago each week. The most common flight departure day for this route is Fri, with 22% of weekly flights taking off on this day.