S$153 Cheap Flights from San Francisco to Chicago

View S$153 flight on Wed, 11 Mar, 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$153 for one-way flights and S$306 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sat, 17 Jan - Wed, 21 Jan
SFO
San Francisco
MDW
Chicago
S$306 Return, found 6 days ago
S$306
Return
found 6 days ago
Select Delta flight, departing Sat, 17 Jan from San Francisco to Chicago, returning Wed, 21 Jan, priced at S$306 found 6 days ago
Delta
Sat, 17 Jan - Mon, 26 Jan
SFO
San Francisco
MDW
Chicago
S$326 Return, found 6 days ago
S$326
Return
found 6 days ago
Select Delta flight, departing Sat, 17 Jan from San Francisco to Chicago, returning Mon, 26 Jan, priced at S$326 found 6 days ago
Delta
Wed, 4 Mar - Tue, 10 Mar
SFO
San Francisco
MDW
Chicago
S$330 Return, found 19 hours ago
S$330
Return
found 19 hours ago
Select Delta flight, departing Wed, 4 Mar from San Francisco to Chicago, returning Tue, 10 Mar, priced at S$330 found 19 hours ago
Delta
Fri, 16 Jan - Mon, 26 Jan
SFO
San Francisco
MDW
Chicago
S$345 Return, found 6 days ago
S$345
Return
found 6 days ago
Select Delta flight, departing Fri, 16 Jan from San Francisco to Chicago, returning Mon, 26 Jan, priced at S$345 found 6 days ago
Delta
Wed, 4 Mar - Tue, 10 Mar
SFO
San Francisco
MDW
Chicago
S$357 Return, found 19 hours ago
S$357
Return
found 19 hours ago
Select Delta flight, departing Wed, 4 Mar from San Francisco to Chicago, returning Tue, 10 Mar, priced at S$357 found 19 hours ago
Delta
Mon, 6 Apr - Sat, 25 Apr
SFO
San Francisco
MDW
Chicago
S$368 Return, found 5 days ago
S$368
Return
found 5 days ago
Select Delta flight, departing Mon, 6 Apr from San Francisco to Chicago, returning Sat, 25 Apr, priced at S$368 found 5 days ago
Delta
Sun, 8 Mar - Wed, 11 Mar
SFO
San Francisco
MDW
Chicago
S$383 Return, found 5 days ago
S$383
Return
found 5 days ago
Select Delta flight, departing Sun, 8 Mar from San Francisco to Chicago, returning Wed, 11 Mar, priced at S$383 found 5 days ago
Delta
Thu, 15 Jan - Wed, 21 Jan
SFO
San Francisco
MDW
Chicago
S$385 Return, found 6 days ago
S$385
Return
found 6 days ago
Select Delta flight, departing Thu, 15 Jan from San Francisco to Chicago, returning Wed, 21 Jan, priced at S$385 found 6 days ago
Delta
Mon, 6 Apr - Fri, 24 Apr
SFO
San Francisco
MDW
Chicago
S$385 Return, found 5 days ago
S$385
Return
found 5 days ago
Select Delta flight, departing Mon, 6 Apr from San Francisco to Chicago, returning Fri, 24 Apr, priced at S$385 found 5 days ago
Delta
Wed, 4 Mar - Sun, 22 Mar
SFO
San Francisco
MDW
Chicago
S$388 Return, found 5 days ago
S$388
Return
found 5 days ago
Select Delta flight, departing Wed, 4 Mar from San Francisco to Chicago, returning Sun, 22 Mar, priced at S$388 found 5 days ago

Find the cheapest month to fly from San Francisco (SFO) to Chicago (MDW)

February is typically the cheapest month to fly

From S$179 - S$521 per traveller.

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city centre is 23 minutes. Flights from S$448
ORD
O'Hare Intl.
Cheapest
Average driving time to city centre23 min
Flights from S$448

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$306. 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$306
Distance
2962 km
Average flight time
6 hours 19 mins

Book with confidence

Perfect flights from San Francisco to Chicago

Your Journey from San Francisco to Chicago

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With Expedia, you have access to a wide range of airlines, including Delta. Our selection of flights from San Francisco Intl. to Midway Intl. caters to every traveler's requirements, ensuring your journey aligns with your schedule. With options from 20 airlines, you're bound to find the perfect flight.
 

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*Note: Prices may vary based on availability and are subject to change.
Perfect flights from San Francisco to Chicago

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