S$133 Cheap Flights from San Francisco to Chicago

View S$133 flight on Mon, 11 May, 2026Opens in a new window

Popular airlines from San Francisco Intl. Airport (SFO) to Chicago Midway Airport (MDW)

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Cheap Flights from San Francisco to Chicago (SFO-MDW)

Prices were available within the past 7 days and start at S$133 for one-way flights and S$364 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Thu, 28 May - Mon, 1 Jun
SFO
San Francisco
MDW
Chicago
S$364 Return, found 21 hours ago
S$364
Return
found 21 hours ago
Select Delta flight, departing Thu, 28 May from San Francisco to Chicago, returning Mon, 1 Jun, priced at S$364 found 21 hours ago
Delta
Sat, 23 May - Sat, 30 May
SFO
San Francisco
MDW
Chicago
S$366 Return, found 5 days ago
S$366
Return
found 5 days ago
Select Delta flight, departing Sat, 23 May from San Francisco to Chicago, returning Sat, 30 May, priced at S$366 found 5 days ago
Delta
Thu, 28 May - Mon, 1 Jun
SFO
San Francisco
MDW
Chicago
S$420 Return, found 21 hours ago
S$420
Return
found 21 hours ago
Select Delta flight, departing Thu, 28 May from San Francisco to Chicago, returning Mon, 1 Jun, priced at S$420 found 21 hours ago
Delta
Sat, 23 May - Sat, 30 May
SFO
San Francisco
MDW
Chicago
S$426 Return, found 5 days ago
S$426
Return
found 5 days ago
Select Delta flight, departing Sat, 23 May from San Francisco to Chicago, returning Sat, 30 May, priced at S$426 found 5 days ago
Delta
Sat, 15 Aug - Sat, 29 Aug
SFO
San Francisco
MDW
Chicago
S$467 Return, found 5 days ago
S$467
Return
found 5 days ago
Select Delta flight, departing Sat, 15 Aug from San Francisco to Chicago, returning Sat, 29 Aug, priced at S$467 found 5 days ago
Delta
Thu, 28 May - Mon, 1 Jun
SFO
San Francisco
MDW
Chicago
S$491 Return, found 21 hours ago
S$491
Return
found 21 hours ago
Select Delta flight, departing Thu, 28 May from San Francisco to Chicago, returning Mon, 1 Jun, priced at S$491 found 21 hours ago
Delta
Sat, 23 May - Sat, 30 May
SFO
San Francisco
MDW
Chicago
S$494 Return, found 5 days ago
S$494
Return
found 5 days ago
Select Delta flight, departing Sat, 23 May from San Francisco to Chicago, returning Sat, 30 May, priced at S$494 found 5 days ago
Delta
Sat, 15 Aug - Sat, 29 Aug
SFO
San Francisco
MDW
Chicago
S$532 Return, found 5 days ago
S$532
Return
found 5 days ago
Select Delta flight, departing Sat, 15 Aug from San Francisco to Chicago, returning Sat, 29 Aug, priced at S$532 found 5 days ago
Delta
Thu, 28 May - Mon, 1 Jun
SFO
San Francisco
MDW
Chicago
S$538 Return, found 21 hours ago
S$538
Return
found 21 hours ago
Select Delta flight, departing Thu, 28 May from San Francisco to Chicago, returning Mon, 1 Jun, priced at S$538 found 21 hours ago
Delta
Sat, 23 May - Sat, 30 May
SFO
San Francisco
MDW
Chicago
S$543 Return, found 5 days ago
S$543
Return
found 5 days ago
Select Delta flight, departing Sat, 23 May from San Francisco to Chicago, returning Sat, 30 May, priced at S$543 found 5 days ago

Frequently asked questions

How much is a flight from San Francisco Airport to Midway Intl. Airport (MDW)?
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$364. Cheap fares don't wait forever, so make sure you book yours ASAP. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from San Francisco Airport to Midway Intl. Airport (MDW)?
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.
How do I find cheap flights from San Francisco Intl. Airport (SFO) to MDW that have flexible change policies?
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.
How far is the flight from San Francisco Intl. Airport (SFO) to Chicago Airport?
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.
Which airlines fly direct from San Francisco Intl. Airport (SFO) to MDW?
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.
Are San Francisco Intl. Airport (SFO) to Midway Intl. Airport (MDW) flight tickets cheaper when they're purchased at the last minute?
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.

Travel information

Origin airport
San Francisco Intl.
Destination airport
Midway Intl.
Airlines serving
Delta
Return price
S$364
Distance
2962 km
Average flight time
6 hours 38 mins

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