S$166 Cheap Flights from San Francisco to Chicago

View S$166 flight on Thu, 25 Dec, 2025Opens 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$166 for one-way flights and S$417 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Mon, 17 Nov - Thu, 20 Nov
SFO
San Francisco
MDW
Chicago
S$417 Return, found 2 days ago
S$417
Return
found 2 days ago
Select Delta flight, departing Mon, 17 Nov from San Francisco to Chicago, returning Thu, 20 Nov, priced at S$417 found 2 days ago
Delta
Sat, 15 Nov - Sat, 22 Nov
SFO
San Francisco
MDW
Chicago
S$468 Return, found 5 days ago
S$468
Return
found 5 days ago
Select Delta flight, departing Sat, 15 Nov from San Francisco to Chicago, returning Sat, 22 Nov, priced at S$468 found 5 days ago
Delta
Tue, 16 Dec - Wed, 24 Dec
SFO
San Francisco
MDW
Chicago
S$475 Return, found 23 hours ago
S$475
Return
found 23 hours ago
Select Delta flight, departing Tue, 16 Dec from San Francisco to Chicago, returning Wed, 24 Dec, priced at S$475 found 23 hours ago
Delta
Mon, 3 Nov - Thu, 6 Nov
SFO
San Francisco
MDW
Chicago
S$478 Return, found 2 days ago
S$478
Return
found 2 days ago
Select Delta flight, departing Mon, 3 Nov from San Francisco to Chicago, returning Thu, 6 Nov, priced at S$478 found 2 days ago
Delta
Mon, 3 Nov - Thu, 6 Nov
SFO
San Francisco
MDW
Chicago
S$540 Return, found 2 days ago
S$540
Return
found 2 days ago
Select Delta flight, departing Mon, 3 Nov from San Francisco to Chicago, returning Thu, 6 Nov, priced at S$540 found 2 days ago
Delta
Tue, 16 Dec - Wed, 24 Dec
SFO
San Francisco
MDW
Chicago
S$551 Return, found 23 hours ago
S$551
Return
found 23 hours ago
Select Delta flight, departing Tue, 16 Dec from San Francisco to Chicago, returning Wed, 24 Dec, priced at S$551 found 23 hours ago
Delta
Mon, 17 Nov - Thu, 20 Nov
SFO
San Francisco
MDW
Chicago
S$554 Return, found 2 days ago
S$554
Return
found 2 days ago
Select Delta flight, departing Mon, 17 Nov from San Francisco to Chicago, returning Thu, 20 Nov, priced at S$554 found 2 days ago
Delta
Sat, 15 Nov - Sat, 22 Nov
SFO
San Francisco
MDW
Chicago
S$584 Return, found 5 days ago
S$584
Return
found 5 days ago
Select Delta flight, departing Sat, 15 Nov from San Francisco to Chicago, returning Sat, 22 Nov, priced at S$584 found 5 days ago
Delta
Wed, 24 Dec - Wed, 7 Jan
SFO
San Francisco
MDW
Chicago
S$617 Return, found 1 day ago
S$617
Return
found 1 day ago
Select Delta flight, departing Wed, 24 Dec from San Francisco to Chicago, returning Wed, 7 Jan, priced at S$617 found 1 day ago
Delta
Tue, 16 Dec - Wed, 24 Dec
SFO
San Francisco
MDW
Chicago
S$655 Return, found 23 hours ago
S$655
Return
found 23 hours ago
Select Delta flight, departing Tue, 16 Dec from San Francisco to Chicago, returning Wed, 24 Dec, priced at S$655 found 23 hours ago

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

February is typically the cheapest month to fly

From S$178 - S$519 per traveller.

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$417. 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

Travel information

Origin airport
San Francisco Intl.
Destination airport
Midway Intl.
Airlines serving
Delta
Return price
S$416
Distance
2962 km
Average flight time
4 hours 5 mins

Book with confidence

Book with confidence

Perfect flights from San Francisco to Chicago

Your Journey from San Francisco to Chicago

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Choosing Your Ideal Flight

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.
 

Maximizing Value with San Francisco to Chicago Flights

Experience the joy of finding cheap flights from San Francisco Intl. to Midway Intl. that fit your budget. Keep an eye out for our special deals and discounts, and check our flexible one-way fares from S$166 and roundtrip prices from S$417*.
 

Pre-Flight Essentials

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Experience the Vibrant Chicago

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Traveling with Expedia is more than just a flight. We offer details about in-flight amenities, baggage policies, and more to ensure a smooth and hassle-free journey. Choose from our variety of airlines and embark on a memorable journey from San Francisco to Chicago.
 

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With Expedia, your adventure extends beyond the flight. Explore Chicago at your own pace by renting a car or booking a hotel. Discover hidden gems off the beaten path and create unforgettable memories.
 

Book Your Flight from San Francisco to Chicago with Confidence

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

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Chicago Airports

Chicago

San Francisco to O'Hare Intl.
S$351.70
*Available to Expedia members.