Cheap flights from San Diego to Chicago from $140

The month of October is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from San Diego averaging around $253.

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Friday when prices can be found for as low as $361. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from San Diego because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $543.

Flying to Chicago O'Hare Intl Airport from San Diego in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $292 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $447. Of course, these prices can vary depending on the time of year and what airport you fly to.

Fly from San Diego to Chicago O'Hare Intl for the best San Diego - Chicago O'Hare Intl flight prices

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from San Diego when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $296 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from San Diego for as low as $257 on momondo.

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

United Airlines, Delta, and Alaska Airlines are the most popular carriers operating from San Diego to Chicago O'Hare Intl

American Airlines, United Airlines and Alaska Airlines are the top three most popular airlines that fly to Chicago O'Hare Intl Airport from San Diego according to our data. American Airlines is the first choice among our users, with 47% of people opting to fly with this airline when traveling to Chicago O'Hare Intl Airport. Keep in mind that there are 8 different airlines that fly to Chicago O'Hare Intl Airport on a routine basis, so you have a few additional options to choose from.

Historically, on average around 10% of flights between San Diego and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 181 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.

Tuesday 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 7% of their flights experiencing any sort of delay.

43 flights are operational daily from San Diego to Chicago O'Hare Intl Airport as of June 2026. The most popular departure time for this route is 10:00AM, with 59% of flights per day taking off at noon.

As of June 2026, 304 flights take off from San Diego and land in Chicago O'Hare Intl Airport each week. The most common flight departure day for this route is Mon, with 17% of weekly flights taking off on this day.