S$147 Cheap Flights from San Francisco to Chicago

Within the past 7 days on Expedia, for flights departing within the next year, the lowest price advertised for a round-trip flight from SFO to Midway Airport was S$387. Cheap fares don’t wait forever, so make sure you book yours ASAP. Prices and availability are subject to change. Additional terms apply.

Most flights can be cancelled online, but every air carrier has its own terms and conditions. If you do need to cancel your flight, visit our Customer Service Portal and follow the instructions.

Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you’re searching for San Francisco Airport to Chicago Airport flights, you’ll see a “no change fees” filter for you to select.

It’s around 3,000 kilometres from San Francisco Intl. Airport (SFO) to Chicago Airport, so you’ll be strapped into your seat for a while. Keep yourself entertained by packing things like playing cards (if you’re travelling with friends) or a good old-fashioned book.

Unfortunately, there are no airlines that directly fly between San Francisco Airport and Midway Intl. Airport (MDW). You’ll need to book a flight with one or more stops.

Flight prices go up and down like a yo-yo, so it’s no sure thing. While last-minute flight deals between SFO and MDW are possible, it’s also a good idea to keep a close eye on prices well before you fly. In fact, some carriers publish their prices up to a year prior to the departure date. Expedia is constantly updating the best airfare bargains around, so keep checking and be ready to pounce when the fares dip.