S$175 Cheap Flights from San Francisco to Chicago

View S$175 flight on Wed, 8 Jul, 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$175 for one-way flights and S$360 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, 19 Aug - Mon, 24 Aug
SFO
San Francisco
MDW
Chicago
S$360 Return, found 4 days ago
S$360
Return
found 4 days ago
Select Delta flight, departing Wed, 19 Aug from San Francisco to Chicago, returning Mon, 24 Aug, priced at S$360 found 4 days ago
Delta
Wed, 19 Aug - Mon, 24 Aug
SFO
San Francisco
MDW
Chicago
S$361 Return, found 4 days ago
S$361
Return
found 4 days ago
Select Delta flight, departing Wed, 19 Aug from San Francisco to Chicago, returning Mon, 24 Aug, priced at S$361 found 4 days ago
Delta
Tue, 7 Jul - Fri, 10 Jul
SFO
San Francisco
MDW
Chicago
S$414 Return, found 6 days ago
S$414
Return
found 6 days ago
Select Delta flight, departing Tue, 7 Jul from San Francisco to Chicago, returning Fri, 10 Jul, priced at S$414 found 6 days ago
Delta
Wed, 19 Aug - Mon, 24 Aug
SFO
San Francisco
MDW
Chicago
S$415 Return, found 4 days ago
S$415
Return
found 4 days ago
Select Delta flight, departing Wed, 19 Aug from San Francisco to Chicago, returning Mon, 24 Aug, priced at S$415 found 4 days ago
Delta
Wed, 19 Aug - Mon, 24 Aug
SFO
San Francisco
MDW
Chicago
S$424 Return, found 4 days ago
S$424
Return
found 4 days ago
Select Delta flight, departing Wed, 19 Aug from San Francisco to Chicago, returning Mon, 24 Aug, priced at S$424 found 4 days ago
Delta
Tue, 21 Jul - Tue, 28 Jul
SFO
San Francisco
MDW
Chicago
S$456 Return, found 2 days ago
S$456
Return
found 2 days ago
Select Delta flight, departing Tue, 21 Jul from San Francisco to Chicago, returning Tue, 28 Jul, priced at S$456 found 2 days ago
Delta
Tue, 7 Jul - Fri, 10 Jul
SFO
San Francisco
MDW
Chicago
S$477 Return, found 6 days ago
S$477
Return
found 6 days ago
Select Delta flight, departing Tue, 7 Jul from San Francisco to Chicago, returning Fri, 10 Jul, priced at S$477 found 6 days ago
Delta
Sat, 25 Jul - Tue, 28 Jul
SFO
San Francisco
MDW
Chicago
S$521 Return, found 2 days ago
S$521
Return
found 2 days ago
Select Delta flight, departing Sat, 25 Jul from San Francisco to Chicago, returning Tue, 28 Jul, priced at S$521 found 2 days ago
Delta
Tue, 16 Jun - Wed, 24 Jun
SFO
San Francisco
MDW
Chicago
S$583 Return, found 1 day ago
S$583
Return
found 1 day ago
Select Delta flight, departing Tue, 16 Jun from San Francisco to Chicago, returning Wed, 24 Jun, priced at S$583 found 1 day ago
Delta
Tue, 21 Jul - Tue, 28 Jul
SFO
San Francisco
MDW
Chicago
S$596 Return, found 2 days ago
S$596
Return
found 2 days ago
Select Delta flight, departing Tue, 21 Jul from San Francisco to Chicago, returning Tue, 28 Jul, priced at S$596 found 2 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$360. 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.
Return price
S$359
Distance
2962 km
Average flight time
6 hours 16 mins

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Perfect flights from San Francisco to Chicago

Your Journey from San Francisco to Chicago

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*Note: Prices may vary based on availability and are subject to change.
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