Cheap flights from Columbia, Missouri to Chicago from $166

The month of January is, on average, the cheapest month to fly to Chicago from Columbia, Missouri, with most prices found around $238. If you’re not able to fly to Chicago in January, then December is your next best option. Flight prices from Columbia, Missouri to Chicago during December average around $266.

The cheapest day to depart on your flight to Chicago is on a Saturday when prices can be found for as low as $404. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Columbia, Missouri to Chicago for around $628.

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Columbia, Missouri to Chicago during this time can be as low as $443. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $544.

Fly from Columbia Regional to Chicago O'Hare Intl for the best Columbia Regional - Chicago flight prices

You are more likely to see cheaper flights to Chicago from Columbia, Missouri when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $307 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Columbia, Missouri for as low as $238 on momondo.

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

United Airlines is the most popular carrier operating from Columbia Regional to Chicago

American Airlines, United Airlines and Contour are the top three most popular airlines that fly to Chicago from Columbia, Missouri according to our data. American Airlines is the first choice among our users, with 54% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 3 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 Columbia, Missouri and Chicago is 7 per day as of September 2026. The most frequent departure time is 5:00AM, with 52% of daily flights leaving at noon.

As of September 2026, there are 52 flights per week flying from Columbia, Missouri to Chicago. The most common day of the week flights depart is Mon, with 19% of flights taking off on this day.