Cheap flights from Indianapolis to Chicago from $69

The month of August is, on average, the cheapest month to fly to Chicago from Indianapolis, with most prices found around $98. If you’re not able to fly to Chicago in August, then January is your next best option. Flight prices from Indianapolis to Chicago during January average around $99.

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $534. 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 Indianapolis to Chicago for around $704.

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Indianapolis to Chicago during this time can be as low as $498. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $885.

Fly from Indianapolis to Chicago Midway for the best Indianapolis - Chicago flight prices

You are more likely to see cheaper flights to Chicago from Indianapolis when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $303 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Indianapolis for as low as $133 on momondo.

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

As of May 2026, prices for Indianapolis to Chicago flights are approximately 11% more expensive when compared to flights at the same time last year.

Delta, Southwest, and American Airlines are the most popular carriers operating from Indianapolis to Chicago

United Airlines, American Airlines and Southwest are the top three most popular airlines that fly to Chicago from Indianapolis according to our data. United Airlines is the first choice among our users, with 56% 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.

As of May 2026, 77 flights take off from Indianapolis and land in Chicago each day. The most common flight departure time for this route is 9:00AM, with 41% of daily flights taking off in the afternoon.

As of May 2026, 543 flights take off from Indianapolis and land in Chicago each week. The most common flight departure day for this route is Mon, with 17% of weekly flights taking off on this day.