Cheap flights from Cincinnati to Chicago from $66

The month of April is, on average, the cheapest month to fly to Chicago from Cincinnati, with most prices found around $272. If you’re not able to fly to Chicago in April, then May is your next best option. Flight prices from Cincinnati to Chicago during May average around $310.

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $512. 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 Cincinnati to Chicago for around $715.

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Cincinnati to Chicago during this time can be as low as $504. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $1,023.

Fly from Cincinnati Cinci./N. Kentucky to Chicago Midway for the best Cincinnati Cinci./N. Kentucky - Chicago flight prices

You are more likely to see cheaper flights to Chicago from Cincinnati when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $383 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Cincinnati for as low as $222 on momondo.

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

You could potentially save up to 11% on your flight if you consider stops on a Cincinnati to Chicago flight.

As of October 2026, prices for Cincinnati to Chicago flights are approximately 0% more expensive when compared to flights at the same time last year.

Frontier, Southwest, and United Airlines are the most popular carriers operating from Cincinnati Cinci./N. Kentucky to Chicago

United Airlines, American Airlines and Southwest are the top three most popular airlines that fly to Chicago from Cincinnati according to our data. United 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 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 Cincinnati and Chicago is 27 per day as of October 2026. The most frequent departure time is 11:00AM, with 57% of daily flights leaving at noon.

As of October 2026, 192 flights take off from Cincinnati and land in Chicago each week. The most common flight departure day for this route is Thu, with 32% of weekly flights taking off on this day.