$99 Cheap Flights from San Francisco (SFO) to Chicago (MDW)

View $99 flight on Sat, Sep 13, 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 $99 for one-way flights and $197 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Wed, Oct 15 - Sat, Oct 18
SFO
San Francisco
MDW
Chicago
$197 Roundtrip, found 4 hours ago
$197
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Wed, Oct 15 from San Francisco to Chicago, returning Sat, Oct 18, priced at $197 found 4 hours ago
Southwest Airlines
Sat, Sep 6 - Wed, Sep 10
SFO
San Francisco
MDW
Chicago
$207 Roundtrip, found 3 hours ago
$207
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Sat, Sep 6 from San Francisco to Chicago, returning Wed, Sep 10, priced at $207 found 3 hours ago
Southwest Airlines
Sat, Sep 6 - Wed, Sep 10
SFO
San Francisco
MDW
Chicago
$217 Roundtrip, found 3 hours ago
$217
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Sat, Sep 6 from San Francisco to Chicago, returning Wed, Sep 10, priced at $217 found 3 hours ago
Southwest Airlines
Wed, Nov 12 - Mon, Nov 17
SFO
San Francisco
MDW
Chicago
$217 Roundtrip, found 5 hours ago
$217
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Wed, Nov 12 from San Francisco to Chicago, returning Mon, Nov 17, priced at $217 found 5 hours ago
Southwest Airlines
Tue, Sep 23 - Sat, Sep 27
SFO
San Francisco
MDW
Chicago
$226 Roundtrip, found 5 days ago
$226
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Tue, Sep 23 from San Francisco to Chicago, returning Sat, Sep 27, priced at $226 found 5 days ago
Delta
Sat, Sep 6 - Wed, Sep 10
SFO
San Francisco
MDW
Chicago
$227 Roundtrip, found 3 hours ago
$227
Roundtrip
found 3 hours ago
Select Delta flight, departing Sat, Sep 6 from San Francisco to Chicago, returning Wed, Sep 10, priced at $227 found 3 hours ago
Delta
Sun, Aug 31 - Wed, Sep 3
SFO
San Francisco
MDW
Chicago
$228 Roundtrip, found 1 day ago
$228
Roundtrip
found 1 day ago
Select Delta flight, departing Sun, Aug 31 from San Francisco to Chicago, returning Wed, Sep 3, priced at $228 found 1 day ago
Southwest Airlines
Fri, Nov 7 - Tue, Nov 11
SFO
San Francisco
MDW
Chicago
$232 Roundtrip, found 12 hours ago
$232
Roundtrip
found 12 hours ago
Select Southwest Airlines flight, departing Fri, Nov 7 from San Francisco to Chicago, returning Tue, Nov 11, priced at $232 found 12 hours ago
Southwest Airlines
Wed, Dec 10 - Wed, Dec 17
SFO
San Francisco
MDW
Chicago
$235 Roundtrip, found 1 day ago
$235
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Dec 10 from San Francisco to Chicago, returning Wed, Dec 17, priced at $235 found 1 day ago
Frontier Airlines
Mon, Aug 11 - Sat, Aug 23
SFO
San Francisco
MDW
Chicago
$243 Roundtrip, found 9 hours ago
$243
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Mon, Aug 11 from San Francisco to Chicago, returning Sat, Aug 23, priced at $243 found 9 hours ago

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

October is typically the cheapest month to fly

From $132 - $347 per traveler.

Graph displaying average flight prices per month

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. Average driving time to city center is 23 minutes. Flights from $258
ORD
O'Hare Intl.
Average driving time to city center23 min
Flights from $258
Flights from San Francisco (SFO) to Chicago (MDW)
Origin airport
San Francisco Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$197
Distance
1851 mi
Average flight time
7 hours 35 mins

San Francisco to Chicago Flights

The cheapest times to fly from San Francisco to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from San Francisco to Chicago are during the month of October. You can find some of the cheapest flights from San Francisco to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from San Francisco to Chicago

Sunday is one of the best days to book for cheap flights from San Francisco to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from San Francisco to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from San Francisco to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $99 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap San Francisco to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your San Francisco to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from San Francisco Intl. Airport (SFO) to Midway Intl. Airport (MDW) cost?
You can find cheap return fares from San Francisco Intl. Airport (SFO) to Midway Intl. Airport (MDW) starting at $197. Reserve your seat and take off on your trip. This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Southwest Airlines and American Airlines flight leaving SFO on August 19 2025 and touching down at MDW. The price was last updated on July 23 2025 and has not changed since.
What is the cheapest month to fly from SFO to MDW?
The cheapest flights from SFO to MDW are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from San Francisco Intl. Airport (SFO) to Midway Intl. Airport (MDW)?
When flying out of San Francisco Intl. Airport (SFO), you can jump on a direct flight to Midway Intl. Airport (MDW) with Southwest Airlines.
What is the cheapest airline that flies from SFO to MDW?
Take off from SFO to MDW with Southwest Airlines. This airline currently has the cheapest one-way fare on this route, starting at $99. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from SFO on October 18 2025. Prices were last updated on July 23 2025 and have not changed since.
How many flights per day from San Francisco Intl. Airport (SFO) to Midway Intl. Airport (MDW)?
On average, there are 4 nonstop flights departing from San Francisco Intl. Airport (SFO) to Midway Intl. Airport (MDW) each week. If you don't see one that works for your schedule, consider a flight that includes a layover. Filter your search results on Expedia to include one or two stops and opt for the next best option.
What are the most popular departure times for flights from San Francisco Intl. Airport (SFO) to Midway Intl. Airport (MDW)?
The 6 AM departures from SFO to MDW are the busiest. They can also be more expensive. If you're hoping to save money, choose a less crowded time to fly.
What day of the week has the most flights from SFO to MDW?
Sunday has the most flights from San Francisco Intl. Airport (SFO) to Midway Intl. Airport (MDW). Consider leaving on this day and you'll have the best chance of finding a schedule that works for you.
What is the earliest flight from San Francisco Intl. Airport (SFO) to Midway Intl. Airport (MDW)?
Hop on the earliest flight at around 6:10AM UTC-8, leaving from San Francisco Intl. Airport (SFO). You'll be in the air for roughly 4h 10m, landing at Midway Intl. Airport (MDW) at approximately 12:20PM UTC-6.
How long does it take to fly from San Francisco Intl. Airport (SFO) to Midway Intl. Airport (MDW)?
Flights from SFO to MDW have an average travel time of 4 hours and 9 minutes. The distance between the two is 1,850 mi.
What is the best time to fly from San Francisco Intl. Airport (SFO) to Midway Intl. Airport (MDW)?
To touch down at Midway Intl. Airport (MDW) on schedule, pick a flight that leaves San Francisco Intl. Airport (SFO) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this hour.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from San Francisco Intl. Airport (SFO)?
Catch a direct flight from San Francisco Intl. Airport (SFO) to Chicago and arrive at O'Hare Intl. Airport (ORD). Another convenient gateway to the city is Midway Intl. Airport (MDW).
Is it cheaper to buy a plane ticket from San Francisco Intl. Airport (SFO) to Midway Intl. Airport (MDW) last-minute?
Waiting until just before your trip to book a ticket from SFO to MDW generally means paying more. While you may come across some last-minute offers, they're not always guaranteed. Be flexible with your travel plans to maximize your chances of snagging a bargain.
Is it cheaper to book a SFO to MDW flight and hotel package?
Securing a SFO to MDW flight and hotel package is typically cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your trip all in one place. Select from our wide range of hotels and then add car rentals, activities and flights to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from San Francisco Intl. Airport (SFO) to Midway Intl. Airport (MDW)?
In most instances, you can reschedule or cancel your SFO to MDW flight. However, additional charges may apply, especially if your booking was made over 24 hours ago. Double-check your itinerary for the airline's fees and guidelines on flight changes, or if you'd like more information, head to our Customer Service portal.

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*Available to One Key members.