Cheap flights from Oklahoma to Chicago from $48

The month of September is, on average, the cheapest month to fly to Chicago from Oklahoma, 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 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 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 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 Tulsa to Chicago O'Hare Intl for the best Oklahoma - Chicago flight prices

You are more likely to see cheaper flights to Chicago from Oklahoma 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 for as low as $244 on momondo.

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

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

American Airlines, United Airlines and Southwest are the top three most popular airlines that fly to Chicago from Oklahoma according to our data. American Airlines is the first choice among our users, with 50% 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.

The number of flights available between Oklahoma and Chicago is 91 per day as of March 2026. The most frequent departure time is 10:00AM, with 50% of daily flights leaving at noon.

As of March 2026, 639 flights take off from Oklahoma and land in Chicago each week. The most common flight departure day for this route is Thu, with 23% of weekly flights taking off on this day.