Cheap Flights from San Francisco International to Chicago Midway

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Compare San Francisco International to Chicago Midway flight deals

Find the cheapest month or even day of the year to fly to Chicago Midway

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Flight deals from San Francisco International to Chicago Midway

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

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

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

Direct flights from San Francisco International to Chicago Midway

San Francisco International to Chicago Midway: Alternative routes

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

San Francisco to Chicago: Flight information

The things to know before you go.
Cheapest flight foundRs27,862
Cheapest month to flyMay
Average flight time4 hrs, 5 mins
Most popular airlineSouthwest Airlines
Average flights per week7

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

The best price we found for a return flight from San Francisco International to Chicago Midway is Rs55,087. 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 5 minutes is the average flight time from San Francisco International to Chicago Midway.
Southwest Airlines flies direct from San Francisco International to Chicago Midway.
As of May 2025, there are 7 flights per week flying from San Francisco International to Chicago Midway.
The cheapest month to fly from San Francisco International to Chicago Midway is usually May 2025.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from San Francisco International Airport to Chicago Midway Airport on Tuesday, 24 June 2025.
Yes – the average flight time is 4 hours and 5 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 Chicago Midway 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 Chicago 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 Chicago Midway.

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

  • The average duration of a direct flight from San Francisco International Airport to Chicago Midway International Airport is 4 hours 10 minutes.

  • Chicago's timezone is UTC-5, which makes Chicago two hours ahead of San Francisco.

  • You can choose from nine weekly San Francisco International Airport to Chicago Midway International Airport flights. The 05:20 departure with Southwest Airlines is the earliest you can take. Southwest Airlines operates the latest service of the day at 13:00.

  • Your SFO to MDW flight won't wait if you're running late, so get to the airport on time. Arrive up to one hour in advance for domestic flights and two hours ahead when you're flying internationally.

  • Be prepared for longer lines in popular months such as August. Arriving up to four hours ahead of an international flight and two hours for a domestic departure will help ensure a smooth travel experience.

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

  • The airline that passengers book most often on this route is Frontier Airlines.

  • Southwest Airlines stands out as the most punctual carrier for SFO to MDW flights, with 90.57% of services arriving on schedule.

  • We make it easy to book a flight with a stopover. To see all your options for tickets from San Francisco International Airport to Chicago Midway International Airport, uncheck 'Direct flights only.' Then, pick a flight offering a stop long enough to visit your chosen city. Stopovers between SFO and MDW include:

    • Denver International Airport

    • Eppley Airfield Airport

    • Sacramento International Airport

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

  • At the moment, Rs27,862 is the lowest price we've seen for a one-way San Francisco International Airport to Chicago Midway International Airport flight. The best price for a return plane ticket is Rs55,087. Keep in mind that fares can change due to demand when booking.

  • Get cheap tickets from SFO to MDW by booking at least six months ahead. According to our research, that's the sweet spot for finding a bargain.

  • Plan your trip for May. That's the cheapest month for flights from San Francisco International Airport to Chicago Midway International Airport. If you're flexible on when you fly, use the 'Whole month' tool to find the cheapest price across each month.

  • Landing cheap flights from SFO to MDW is a cinch with Price Alerts. Simply create one of these automatic alerts and we'll notify you when fares go down.

  • Tailor your trip with filters. Select your ideal departure and arrival times, total journey duration and airlines. You can also sort your results by 'Cheapest,' 'Fastest' or 'Best' flights from San Francisco International Airport to Chicago Midway International Airport.

Handy information about San Francisco International Airport (SFO)

  • 77.36% of flights departing from San Francisco International Airport make it to their destination on schedule.

  • To reach San Francisco International Airport from central San Francisco, it takes about 20 minutes by car. This depends on traffic, however. It's approximately 21 kilometres from the airport to the city centre.

  • Planning to take public transport? Expect a journey time of around 45 minutes.

  • Get your journey off to a hassle-free start by staying near SFO. Whether you've booked an early flight from San Francisco International Airport to Chicago Midway International Airport or just don't want to be rushed, these stays are perfect:

Arriving at Chicago Midway International Airport (MDW)

  • The last thing you want is a lengthy trip to your hotel if you're getting in late on a San Francisco International Airport to Chicago Midway International Airport flight. Reserve one of these accommodation options near MDW instead:

  • Pick up a Chicago Midway International Airport rental car and explore Chicago and beyond with your own wheels. Dollar, Hertz and Budget are well-known companies you can book with here.

  • To lock in the lowest price, book your vehicle from Chicago Midway International Airport around four weeks before your trip.

Getting from Chicago Midway International Airport (MDW) to central Chicago

  • MDW is located at 5700 South Cicero.

  • Chicago Midway International Airport to the centre of Chicago has a drive time of about 20 minutes. It's approximately 19 kilometres away.

  • It typically takes 45 minutes if you're using public transport.

When to fly to Chicago Midway International Airport (MDW)

  • The quietest month for a flight from San Francisco International Airport to Chicago Midway International Airport is May, while July is the busiest. Pick the ideal time to visit Chicago based on whether you prefer a more relaxed vibe or a faster pace.

  • When booking your flight from San Francisco International Airport to Chicago Midway International Airport, think about the type of weather you like. July is the warmest month in Chicago, with the temperature ranging from 15ºC to 29ºC.

  • January has average temperatures of between -12ºC and 3ºC. Look for cheap tickets from SFO to MDW sometime around then if you like travelling in cooler conditions.

Explore more of United States

  • You've done Chicago, now it's time to explore more of United States. Journey about 451 kilometres south-east to Columbus to check off its top attractions. From Franklin Park Conservatory and Botanical Gardens to Ohio Statehouse and German Village, you've got a jam-packed schedule ahead.

  • Around 257 kilometres south-east of Chicago, Indianapolis is another favourite stop in United States. Experience this destination's highlights firsthand at The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

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