Cheap flights from Chicago Midway to San Francisco International

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Flight deals from Chicago Midway to San Francisco International

Looking for a cheap last-minute deal or the best round-trip flight from Chicago Midway to San Francisco International? Find the lowest prices on one-way and round-trip tickets right here.

Find the cheapest month to fly from Chicago Midway to San Francisco International

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago Midway to San Francisco International flights are currently cheapest in June.

Direct flights from Chicago Midway to San Francisco International

Chicago Midway to San Francisco International: Alternative routes

Compare routes from Chicago Midway to San Francisco below. You may find an airport to fly into that's cheaper, faster, or easier than San Francisco International.

Chicago to San Francisco: Flight information

The things to know before you go.
Cheapest flight found$150
Cheapest month to flyOctober
Average flight time4 hrs, 36 mins
Most popular airlineSouthwest Airlines
Average flights per week8

Finding cheap flights from Chicago Midway to San Francisco International: Frequently asked questions

The best price we found for a round-trip flight from Chicago Midway to San Francisco International is $150. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
4 hours and 36 minutes is the average flight time from Chicago Midway to San Francisco International.
Southwest Airlines flies direct from Chicago Midway to San Francisco International.
There are 8 flights per week flying from Chicago Midway to San Francisco International, as of May 2025.
The cheapest month to fly from Chicago Midway to San Francisco International is usually May 2025.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago Midway Airport to San Francisco International Airport on Thursday, October 30, 2025.
Yes – the average flight time is 4 hours and 36 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to San Francisco International but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar, and it looks like the cheapest time to book a flight to San Francisco is around 40 days in advance, so don’t leave your flight to the last minute.
Currently, Southwest Airlines offers the cheapest flight tickets to San Francisco International.

Flying from Chicago Midway International Airport (MDW) to San Francisco International Airport (SFO): what you need to know

  • Around 4 hours 35 minutes is how long you can expect to be traveling on a direct flight from Chicago Midway International Airport to San Francisco International Airport.

  • The timezone in San Francisco is UTC-7, which is two hours behind Chicago.

  • Every week, there are nine Chicago Midway International Airport to San Francisco International Airport flights. If you want to get going as soon as possible, go for the 07:35 Southwest Airlines flight. If you'd rather make the most of your time before you fly, the last flight is at 22:20 with Southwest Airlines.

  • Leave plenty of time to make your MDW to SFO flight. As a general rule, arrive at least two hours before international departures and an hour ahead for domestic flights.

  • You can expect longer lines during popular months like July. Arriving up to four hours ahead of international flights and two hours for a domestic departure is a good idea.

  • Jetting into San Francisco (and then seeing more of United States!) is a breeze with Frontier Airlines. This popular airline offers direct flights from Chicago Midway International Airport to San Francisco International Airport.

  • Most travelers choose to travel with Frontier Airlines on this route.

  • Southwest Airlines is the most punctual carrier that operates MDW to SFO flights.

  • Think about adding a stopover when booking your ticket from Chicago Midway International Airport to San Francisco International Airport. Simply deselect 'Direct flights only' to break up your trip, or perhaps see a new city along the way. Here's where you can stop between MDW and SFO:

    • Denver International Airport

    • Eppley Airfield Airport

    • Phoenix Sky Harbor International Airport

How to find the cheapest flights from Chicago Midway International Airport (MDW) to San Francisco International Airport (SFO)

  • $66 is the lowest price for a one-way Chicago Midway International Airport to San Francisco International Airport flight. Return flights start from $150. These fares can change based on availability and demand.

  • Score cheap tickets from MDW to SFO by booking six months ahead. Based on our research, that's the sweet spot for finding a bargain.

  • May is the cheapest month for flights from Chicago Midway International Airport to San Francisco International Airport. If you prefer to travel at a different time of year, the 'Whole month' tool will give you the lowest prices for every month.

  • Spend less time searching for cheap flights from MDW to SFO by setting up a Price Alert. You'll get an email or push notification on the app when a lower fare pops up.

  • Choose your ideal arrival and departure times, number of stops and airlines with the filters. Or sort your results by 'Cheapest' to find the best deals on flights from Chicago Midway International Airport to San Francisco International Airport.

Handy information about Chicago Midway International Airport (MDW)

  • MDW is located at 5700 South Cicero.

  • Of the departures from Chicago Midway International Airport, 77.88% arrive as scheduled at their destination.

  • To reach Chicago Midway International Airport from central Chicago, it takes about 20 minutes if you're going by car. Of course, this depends on traffic. It's approximately 19 kilometers from the airport to the city center.

  • Expect a trip time of about 45 minutes when using public transport.

  • Need a convenient hotel near MDW? If you're boarding an early flight from Chicago Midway International Airport to San Francisco International Airport, these accommodation options will put you moments from your departure lounge:

Arriving at San Francisco International Airport (SFO)

Getting from San Francisco International Airport (SFO) to central San Francisco

  • From San Francisco International Airport, San Francisco is approximately 21 kilometers away. It takes around 20 minutes to reach the center by car.

  • Traveling by public transport takes around 45 minutes.

When to fly to San Francisco International Airport (SFO)

  • August is the busiest month for flights from Chicago Midway International Airport to San Francisco International Airport. For a quieter experience, head to San Francisco in February.

  • Lock in your flight from Chicago Midway International Airport to San Francisco International Airport for September if you'd like to go to San Francisco during its warmest month. Expect temperatures of between 12ºC (54ºF) and 22ºC (72ºF).

  • If you want cooler conditions, look for a cheap ticket from MDW to SFO in January. Average temperatures are between 6ºC (43ºF) and 16ºC (61ºF) then.

Explore more of United States

  • San Jose is just one of the many cities in United States waiting to be discovered once you've seen the sights of San Francisco. Around 64 kilometers away to the south-east, check out popular attractions including Winchester Mystery House, Rosicrucian Egyptian Museum and San Jose Museum of Art.

  • Around 257 kilometers south-east of San Francisco, Fresno is another essential stop in United States. Start your sightseeing at Forestiere Underground Gardens, Fresno Chaffee Zoo and Shinzen Japanese Garden.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.