S$166 Cheap Flights from San Francisco to Chicago

View S$166 flight on Sun, 4 Jan, 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$166 for one-way flights and S$330 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, 13 Aug - Sat, 16 Aug
SFO
San Francisco
MDW
Chicago
S$330 Return, found 6 days ago
S$330
Return
found 6 days ago
Select Delta flight, departing Wed, 13 Aug from San Francisco to Chicago, returning Sat, 16 Aug, priced at S$330 found 6 days ago
Delta
Wed, 27 Aug - Sun, 31 Aug
SFO
San Francisco
MDW
Chicago
S$332 Return, found 13 hours ago
S$332
Return
found 13 hours ago
Select Delta flight, departing Wed, 27 Aug from San Francisco to Chicago, returning Sun, 31 Aug, priced at S$332 found 13 hours ago
Delta
Wed, 13 Aug - Sat, 16 Aug
SFO
San Francisco
MDW
Chicago
S$379 Return, found 6 days ago
S$379
Return
found 6 days ago
Select Delta flight, departing Wed, 13 Aug from San Francisco to Chicago, returning Sat, 16 Aug, priced at S$379 found 6 days ago
Delta
Wed, 27 Aug - Sun, 31 Aug
SFO
San Francisco
MDW
Chicago
S$383 Return, found 3 days ago
S$383
Return
found 3 days ago
Select Delta flight, departing Wed, 27 Aug from San Francisco to Chicago, returning Sun, 31 Aug, priced at S$383 found 3 days ago
Delta
Wed, 13 Aug - Sat, 16 Aug
SFO
San Francisco
MDW
Chicago
S$427 Return, found 6 days ago
S$427
Return
found 6 days ago
Select Delta flight, departing Wed, 13 Aug from San Francisco to Chicago, returning Sat, 16 Aug, priced at S$427 found 6 days ago
Delta
Wed, 13 Aug - Sat, 16 Aug
SFO
San Francisco
MDW
Chicago
S$434 Return, found 6 days ago
S$434
Return
found 6 days ago
Select Delta flight, departing Wed, 13 Aug from San Francisco to Chicago, returning Sat, 16 Aug, priced at S$434 found 6 days ago
Delta
Fri, 8 Aug - Fri, 15 Aug
SFO
San Francisco
MDW
Chicago
S$436 Return, found 1 day ago
S$436
Return
found 1 day ago
Select Delta flight, departing Fri, 8 Aug from San Francisco to Chicago, returning Fri, 15 Aug, priced at S$436 found 1 day ago
Delta
Fri, 4 Jul - Tue, 15 Jul
SFO
San Francisco
MDW
Chicago
S$448 Return, found 5 days ago
S$448
Return
found 5 days ago
Select Delta flight, departing Fri, 4 Jul from San Francisco to Chicago, returning Tue, 15 Jul, priced at S$448 found 5 days ago
Delta
Wed, 13 Aug - Sat, 16 Aug
SFO
San Francisco
MDW
Chicago
S$483 Return, found 6 days ago
S$483
Return
found 6 days ago
Select Delta flight, departing Wed, 13 Aug from San Francisco to Chicago, returning Sat, 16 Aug, priced at S$483 found 6 days ago
Delta
Fri, 4 Jul - Tue, 15 Jul
SFO
San Francisco
MDW
Chicago
S$499 Return, found 5 days ago
S$499
Return
found 5 days ago
Select Delta flight, departing Fri, 4 Jul from San Francisco to Chicago, returning Tue, 15 Jul, priced at S$499 found 5 days ago

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

September is typically the cheapest month to fly

From S$75 - S$422 per traveller.

Graph displaying average flight prices per month

San Francisco to Chicago route information
Origin airport
San Francisco Intl.
Destination airport
Midway Intl.
Airlines serving
Delta
Return price
S$330
Distance
2962 km
Average flight time
7 hours 5 mins

Perfect flights from San Francisco to Chicago

Your Journey from San Francisco to Chicago

Start your unforgettable journey with Expedia. Our broad selection of flights from San Francisco to Chicago caters to every travel need. Whether you're yearning for a romantic escape, a solo adventure, or a cultural immersion, we've got you covered.
 

Choosing Your Ideal Flight

With Expedia, you have access to a wide range of airlines, including Delta, Alaska Airlines. 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$330*.
 

Pre-Flight Essentials

Ensure a smooth journey from San Francisco to Chicago with Expedia. From information about check-in times and in-flight amenities to guidance on baggage policies, we provide all the essentials to prepare you for your flight.
 

Experience the Vibrant Chicago

Picture yourself stepping off the plane in Chicago and immersing yourself in the unique atmosphere of Chicago. From local markets to cultural festivals, each city offers its distinct charm. Make the most of your trip by exploring local attractions and indulging in the local cuisine. With Expedia, explore all this and more, tailored to your budget.
 

Added Convenience on Your San Francisco to Chicago Flight

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.
 

Beyond the Flight – Exploring Chicago

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

Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support make your travel experience seamless and stress-free. Embark on your journey from San Francisco to Chicago with confidence. Book your travel arrangements with Expedia today.
 
*Note: Prices may vary based on availability and are subject to change.

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$330. 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.

Explore a world of travel with Expedia

Chicago Airports

Chicago

San Francisco to O'Hare Intl.
S$331.20
*Available to Expedia members.