Cheap flights from Chicago Midway Airport to San Francisco from $101

According to our data, Monday is the cheapest day to fly to Oakland, California from Chicago Midway Airport. The lowest ticket price found for a Monday departure recently was $333. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Chicago Midway Airport to Oakland, California for around $623.

In the evening is the cheapest time of day to fly from Chicago Midway Airport to Oakland, California when you can find flight prices for as low as $287. Flying to Oakland, California in the evening is an ideal time because this is during off-peak travel hours. Flights in the morning are often more expensive with an average ticket price of $592.

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

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

No. A direct flight is the cheapest option for a flight between Chicago Midway Airport to Oakland, California.

Historically, on average around 28% of flights between Chicago and Oakland have experienced a delay on any given week. The average delay length over the past 12 months has been 121 minutes.

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

Friday 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 28% of their flights experiencing any sort of delay.

As of March 2026, there are 2 flights per day flying from Chicago Midway Airport to Oakland, California. The most common time of day flights depart is 10:00AM, with 50% of flights taking off at noon.

17 flights are operational weekly from Chicago Midway Airport to Oakland, California as of March 2026. The most popular departure day for this route is Mon, with 24% of flights per week taking off on this day.