Cheap flights from Omaha to Chicago from $74

The month of August is, on average, the cheapest month to fly to Chicago from Omaha, with most prices found around $228. If you’re not able to fly to Chicago in August, then January is your next best option. Flight prices from Omaha to Chicago during January average around $277.

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $490. 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 Omaha to Chicago for around $716.

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Omaha to Chicago during this time can be as low as $480. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $797.

Fly from Omaha Eppley Airfield to Chicago Midway for the best Omaha Eppley Airfield - Chicago flight prices

You are more likely to see cheaper flights to Chicago from Omaha when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $318 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Omaha for as low as $188 on momondo.

There are 4 cabin classes available to choose from on Omaha Eppley Airfield 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 6% on your flight if you consider stops on a Omaha to Chicago flight.

As of March 2026, prices for Omaha to Chicago flights are approximately 31% more expensive when compared to flights at the same time last year.

Southwest, United Airlines, and Delta are the most popular carriers operating from Omaha Eppley Airfield to Chicago

United Airlines, American Airlines and Southwest are the top three most popular airlines that fly to Chicago from Omaha according to our data. United Airlines is the first choice among our users, with 62% 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.

Historically, on average around 11% of flights between Omaha and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 118 minutes.

Generally, flights departing at night tend to experience fewer delays. Flights in the evening have, in the past, seen delays more frequently in comparison.

Monday is statistically the day of the week which experiences the fewest number of delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.

According to our data, United Airlines have had the least number of delays on this route over the last 12 months; with about 9% of their flights experiencing any sort of delay.

The number of flights available between Omaha and Chicago is 36 per day as of March 2026. The most frequent departure time is 1:00PM, with 51% of daily flights leaving in the afternoon.

256 flights are operational weekly from Omaha to Chicago as of March 2026. The most popular departure day for this route is Fri, with 16% of flights per week taking off on this day.