Cheap flights from Los Angeles to Chicago from $99

The month of September is, on average, the cheapest month to fly to Chicago Midway Airport from Los Angeles, with most prices found around $285. If you are unable to visit Chicago Midway Airport during the month of September, then departing from Los Angeles during the month August is also very affordable. Most momondo users find prices during this month for around $297.

According to our data, Saturday is the cheapest day to fly to Chicago Midway Airport from Los Angeles. The lowest ticket price found for a Saturday departure recently was $363. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Los Angeles because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $453.

Flying to Chicago Midway Airport from Los Angeles in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $351 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $444. Of course, these prices can vary depending on the time of year and what airport you fly to.

Fly from Los Angeles Los Angeles to Chicago Midway for the best Los Angeles Los Angeles - Chicago Midway flight prices

You are more likely to see cheaper flights to Chicago Midway Airport from Los Angeles when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $347 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from Los Angeles for as low as $274 on momondo.

There is only 1 cabin class available to choose from on Los Angeles Los Angeles to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Southwest and Delta are the most popular carriers operating from Los Angeles Los Angeles to Chicago Midway

Southwest, Frontier and Delta are the top three most popular airlines that fly to Chicago Midway Airport from Los Angeles according to our data. Southwest is the first choice among our users, with 85% of people opting to fly with this airline when traveling to Chicago Midway Airport. Keep in mind that there are 5 different airlines that fly to Chicago Midway Airport on a routine basis, so you have a few additional options to choose from.

Historically, on average around 12% of flights between Los Angeles and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 131 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.

Saturday 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, Southwest have had the least number of delays on this route over the last 12 months; with about 11% of their flights experiencing any sort of delay.

As of March 2026, there are 3 flights per day flying from Los Angeles to Chicago Midway Airport. The most common time of day flights depart is 11:00PM, with 33% of flights taking off at noon.

25 flights are operational weekly from Los Angeles to Chicago Midway Airport as of March 2026. The most popular departure day for this route is Mon, with 20% of flights per week taking off on this day.