Cheap flights from California to Chicago from $108

The month of February is, on average, the cheapest month to fly to Chicago Midway Airport from California, with most prices found around $397. If you are unable to visit Chicago Midway Airport during the month of February, then departing from California during the month April is also very affordable. Most momondo users find prices during this month for around $400.

According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from California. The lowest ticket price found for a Wednesday departure recently was $435. 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, Monday is the most expensive day to depart from California because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $501.

Flying to Chicago Midway Airport from California in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $411 when looking at flights departing in the afternoon. Try not to purchase tickets in the evening because they tend to be around $489. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

You are more likely to see cheaper flights to Chicago Midway Airport from California when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $417 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 California for as low as $327 on momondo.

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

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

Southwest, Frontier and Delta are the top three most popular airlines that fly to Chicago Midway Airport from California according to our data. Southwest is the first choice among our users, with 93% of people opting to fly with this airline when traveling to Chicago Midway Airport. Keep in mind that there are 6 different airlines that fly to Chicago Midway Airport on a routine basis, so you have a few additional options to choose from.

As of October 2026, there are 13 flights per day flying from California to Chicago Midway Airport. The most common time of day flights depart is 11:00PM, with 44% of flights taking off in the evening.

As of October 2026, 95 flights take off from California and land in Chicago Midway Airport each week. The most common flight departure day for this route is Mon, with 28% of weekly flights taking off on this day.