The cheapest times to fly from SFO to MDW are
- January 1st to February 25th (except the week of February 12th)
- April 23rd to May 6th
- August 6th to November 18th
- early December
based on data collected exclusively by Champion Traveler across tens of millions of flights. Among all the dates above, the very cheapest time to fly from SFO to MDW is early December. Prices can be as high as $1178 for Sunday flights during late March, or as low as $266 for Tuesday flights around early December.
When to Fly to Chicago
Flying from San Francisco, CA (SFO) to Chicago, IL (MDW) will usually cost between $278 to $695 per person if booking more than four weeks in advance. On average the very cheapest time to fly is early December with an average ticket price of $297. Due to high demand the most expensive time to fly is late March, with an average price of $607. Planning your trip to low-cost times can easily save you $310 on economy flights and even more on first-class flights. Generally, any price below $354 can be considered a good price for a round-trip SFO to MDW flight.
See below for a graph of average weekly prices for the SFO to MDW route. All prices are for round-trip tickets in USD.
Compared to other flights, the SFO to MDW flight is much cheaper than the average and costs much less than the average flight leaving from San Francisco. The average price per mile (for a direct flight) is $0.12, which is far below average.
Flight Prices by Day of the Week
Tuesday is usually the cheapest day to depart and return on this flight. Sundays are the most expensive days to fly out or take a return trip. Selecting flights on the least expensive days could save you up to $178 (35%) on this flight.
Departing prices are for round-trip flights returning on the day of departure. For example, a flight departing on Tuesday and returning a week later will cost an average of $326. Return trip prices are from the MDW to SFO flight, and often highlight the quality of our data in showing the same trend.
Departing Prices by Day
Return Trip Prices by Day
Nonstop Flights and Layovers
Travelers looking to fly from SFO to MDW can generally find a 0-layover flight. Because there is a direct flight option the real-world direct flight time of 4 hour 19 minutes may be realistic.
Alternative Nearby Airports
Champion Traveler tells you which airports are nearby and whether tickets might be cheaper alternative airports nearby. Sometimes it’s worth it to fly into a closer airport and then commute to your destination. Remember that there is a nonstop flight from SFO to MDW while comparing.
- 15 miles (24 km) away from MDW
- Usually 12.99% less expensive than MDW
- Nonstop flights available
- 81 miles (130 km) away from MDW
- Usually 12.43% less expensive than MDW
- 1-layover flights available
Flight Questions Answered
Still have questions about flying from SFO to MDW? We’ve got answers.
Which airlines fly this route?
You can find 4 major airlines flying this route most often: Alaska, Delta, Southwest, United, and potentially more during busy seasons.
How far away is it from Chicago Midway International Airport to San Francisco International Airport?
The distance between the two airports is roughly 1850 miles or 2977 kilometers.
How long does it take to fly from SFO to MDW?
The real-world flight time for a nonstop SFO to MDW flight is about 4 hour 19 minutes.
How many flights go between San Francisco, CA and Chicago, IL?
It depends on the day of the week and the date, but a typical day might have around 78 available flights from SFO to MDW.
Airport Location Info
|Origination airport name||San Francisco International Airport|
|City||San Francisco, CA|
|Country||the United States|
|Destination airport name||Chicago Midway International Airport|
|Country||the United States|
Late and Early Flight Data
Flights from SFO to MDW tend to depart as late as the average flight. According to our recently updated data, 30% of flights departed 5 or more minutes late, and 0% of flights left 5 or more minutes early. On average you can expect to leave MDW heading for SFO about 6 minutes late. This does not significantly impact arrival time, as the average landing time in Chicago, IL is about 6 minutes early. The numbers below show a recent average of take-off times versus the scheduled departure flight:
- Southwest: 6 minutes late
- Some airlines not reporting
Please note that while we’ve worked hard to analyzed tens of millions of flights to get you this data, we do not calculate current live prices or guarantee pricing. Please see our partners using the links above for current offers.