$73 Cheap Flights from Chicago (MDW) to San Francisco (SFO)

View $73 flight on Sat, Dec 13, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to San Francisco Intl. Airport (SFO)

Cheap Flights from Chicago to San Francisco (MDW-SFO)

Prices were available within the past 7 days and start at $73 for one-way flights and $133 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Fri, Oct 24 - Mon, Oct 27
MDW
Chicago
SFO
San Francisco
$133 Roundtrip, found 4 days ago
$133
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Fri, Oct 24 from Chicago to San Francisco, returning Mon, Oct 27, priced at $133 found 4 days ago
Southwest Airlines
Sat, Nov 1 - Tue, Nov 11
MDW
Chicago
SFO
San Francisco
$138 Roundtrip, found 6 days ago
$138
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Sat, Nov 1 from Chicago to San Francisco, returning Tue, Nov 11, priced at $138 found 6 days ago
Southwest Airlines
Sat, Nov 15 - Mon, Nov 17
MDW
Chicago
SFO
San Francisco
$139 Roundtrip, found 4 days ago
$139
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Sat, Nov 15 from Chicago to San Francisco, returning Mon, Nov 17, priced at $139 found 4 days ago
Southwest Airlines
Wed, Sep 24 - Mon, Sep 29
MDW
Chicago
SFO
San Francisco
$149 Roundtrip, found 4 days ago
$149
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Wed, Sep 24 from Chicago to San Francisco, returning Mon, Sep 29, priced at $149 found 4 days ago
Southwest Airlines
Sat, Nov 1 - Tue, Nov 11
MDW
Chicago
SFO
San Francisco
$153 Roundtrip, found 6 days ago
$153
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Sat, Nov 1 from Chicago to San Francisco, returning Tue, Nov 11, priced at $153 found 6 days ago
Southwest Airlines
Thu, Dec 4 - Mon, Dec 8
MDW
Chicago
SFO
San Francisco
$155 Roundtrip, found 4 days ago
$155
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Thu, Dec 4 from Chicago to San Francisco, returning Mon, Dec 8, priced at $155 found 4 days ago
Southwest Airlines
Fri, Oct 17 - Mon, Oct 20
MDW
Chicago
SFO
San Francisco
$159 Roundtrip, found 6 days ago
$159
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Fri, Oct 17 from Chicago to San Francisco, returning Mon, Oct 20, priced at $159 found 6 days ago
Southwest Airlines
Thu, Dec 4 - Mon, Dec 8
MDW
Chicago
SFO
San Francisco
$165 Roundtrip, found 4 days ago
$165
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Thu, Dec 4 from Chicago to San Francisco, returning Mon, Dec 8, priced at $165 found 4 days ago
Delta
Fri, Oct 31 - Tue, Nov 4
MDW
Chicago
SFO
San Francisco
$227 Roundtrip, just found
$227
Roundtrip
just found
Select Delta flight, departing Fri, Oct 31 from Chicago to San Francisco, returning Tue, Nov 4, priced at $227 just found
Frontier Airlines
Fri, Sep 5 - Fri, Sep 12
MDW
Chicago
SFO
San Francisco
$281 Roundtrip, found 2 hours ago
$281
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Fri, Sep 5 from Chicago to San Francisco, returning Fri, Sep 12, priced at $281 found 2 hours ago

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

October is typically the cheapest month to fly

From $128 - $338 per traveler.

Graph displaying average flight prices per month

Flights from Chicago (MDW) to San Francisco (SFO)
Origin airport
Midway Intl.
Destination airport
San Francisco Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$133
Distance
1851 mi
Average flight time
3 hours 6 mins

Chicago to San Francisco Flights

The cheapest times to fly from Chicago to San Francisco

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 Chicago to San Francisco are during the month of October. You can find some of the cheapest flights from Chicago to San Francisco with Expedia's search tool and vast selection of airlines.

 

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

Sunday is one of the best days to book for cheap flights from Chicago to San Francisco: 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 Chicago to San Francisco

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 Chicago to San Francisco in 2025. You can also book with separate airlines for your outbound and return journeys, from $73 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 Chicago to San Francisco 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 Chicago to San Francisco 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 Midway Intl. Airport (MDW) to San Francisco Intl. Airport (SFO) cost?
Grab cheap return flights starting from $106 from Midway Intl. Airport (MDW) to San Francisco Intl. Airport (SFO). 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 United flight leaving MDW on August 9 2025 and touching down at SFO. The price was last updated on July 13 2025 and has not changed since.
What is the cheapest month to fly from MDW to SFO?
The cheapest flights from MDW to SFO 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 Midway Intl. Airport (MDW) to San Francisco Intl. Airport (SFO)?
Take a nonstop flight with Southwest Airlines and journey straight from Midway Intl. Airport (MDW) to San Francisco Intl. Airport (SFO).
What is the cheapest airline that flies from MDW to SFO?
Take off from MDW to SFO with Southwest Airlines. This carrier currently has the cheapest one-way ticket for this route, starting from $53. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from MDW on October 7 2025. Prices were last updated on July 13 2025 and have not changed since.
How many flights per day from Midway Intl. Airport (MDW) to San Francisco Intl. Airport (SFO)?
On average, you can pick from 4 direct flights each week from Midway Intl. Airport (MDW) to San Francisco Intl. Airport (SFO). To broaden your travel options, consider taking a flight with a layover. Simply enter your details on Expedia and then set the filters to include one stop or more.
What are the most popular departure times for flights from Midway Intl. Airport (MDW) to San Francisco Intl. Airport (SFO)?
More travelers fly between MDW and SFO at 4 PM than at any other time. Looking for a quieter experience? Pick a flight outside the busiest times and you could save on your fare as well.
What day of the week has the most flights from MDW to SFO?
Depart on a Friday if you're searching for the biggest selection of flights from Midway Intl. Airport (MDW) to San Francisco Intl. Airport (SFO).
What is the earliest flight from Midway Intl. Airport (MDW) to San Francisco Intl. Airport (SFO)?
Midway Intl. Airport (MDW)'s first flight to San Francisco Intl. Airport (SFO) is at approximately 9:05AM UTC-6. With a flight time of 4h 55m, you'll land at around 12:00PM UTC-8.
How long does it take to fly from Midway Intl. Airport (MDW) to San Francisco Intl. Airport (SFO)?
The average flight time from MDW to SFO is 4 hours and 55 minutes, covering a total distance of 1,850 mi.
What is the best time to fly from Midway Intl. Airport (MDW) to San Francisco Intl. Airport (SFO)?
To avoid potential delays on the Midway Intl. Airport (MDW) to San Francisco Intl. Airport (SFO) route, travel before 3 PM. Later departures have a 22% higher chance of being canceled.**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 San Francisco from Midway Intl. Airport (MDW)?
Midway Intl. Airport (MDW) offers direct flights to San Francisco. Here are some of the airports you can fly to without stops:

  • San Francisco Intl. Airport (SFO)
  • Norman Y. Mineta San Jose Intl. Airport (SJC)
  • Oakland Intl. Airport (OAK)

Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to San Francisco Intl. Airport (SFO) last-minute?
Booking your flight from MDW to SFO shortly before your trip is generally more expensive. However, if you're flexible with your travel times and dates, you could score a cheap last-minute fare.
Is it cheaper to book a MDW to SFO flight and hotel package?
Securing a MDW to SFO flight and hotel package tends to be 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 accommodations 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 Midway Intl. Airport (MDW) to San Francisco Intl. Airport (SFO)?
If you reserved your MDW to SFO flight within the last 24 hours, you may be able to modify or cancel it at no cost. Depending on the airline and the fare type you purchased, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, visit our Customer Service portal for further details.

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*Available to One Key members.