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$129+ Cheap flights from Midway (MDW) to San Francisco (SFO)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/6. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SFO
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
1 adult, Economy
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Cheap flight deals from Midway to San Francisco

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to San Francisco (SFO). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated November 13, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$249
(Southwest)

One-way from

$129
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$390

Good round-trip deal

$309 or less

Good one-way deal

$249 or less
Provider with most accurate pricing for Chicago Midway-San Francisco flight deals.
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Provider most trusted by Cheapflights users for Chicago Midway-San Francisco flights.
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From Chicago Midway to San Francisco
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One-way flight from Chicago Midway to San Francisco
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Highest demand for flights based on searches. 5% potential increase in price ($25 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Price to beat on a round-trip flight from Chicago Midway to San Francisco.
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Price to beat on a one-way flight from Chicago Midway to San Francisco.
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Find flight deals from Midway to San Francisco

Cheapest flights from Midway to San Francisco
Explore the most affordable flight options available from Midway to San Francisco. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 13, 2025.

This Southwest deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/59:40 amMDW - SFO
1 stop7h 00mSouthwest
Mon 12/86:10 amSFO - MDW
Nonstop4h 05mSouthwest
Deal found 11/10$249
This Kiwi.com deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/2110:50 pmMDW - SFO
2 stops24h 59mFrontier
Sat 12/2711:32 amSFO - MDW
1 stop24h 27mFrontier
Deal found 11/11$251
This Southwest deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/68:15 amMDW - SFO
Nonstop4h 45mSouthwest
Sat 12/135:30 amSFO - MDW
2 stops9h 00mSouthwest
Deal found 11/11$254
This Kiwi.com deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/247:10 pmMDW - SFO
2 stops38h 58mFrontier
Fri 11/286:32 amSFO - MDW
1 stop9h 40mFrontier
Deal found 11/11$257
This Delta deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/69:29 amMDW - SFO
1 stop6h 54mDelta
Thu 1/812:47 amSFO - MDW
1 stop6h 21mDelta
Deal found 11/10$259
This Frontier deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/186:12 amMDW - SFO
1 stop9h 01mFrontier
Sun 1/116:15 amSFO - MDW
1 stop11h 47mFrontier
Deal found 11/11$260
This Frontier deal was found by Cheapflights users on 11/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/296:12 amMDW - SFO
1 stop9h 01mFrontier
Fri 1/96:15 amSFO - MDW
1 stop11h 47mFrontier
Deal found 11/12$261
This Frontier deal was found by Cheapflights users on 11/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/216:00 amMDW - SFO
1 stop9h 13mFrontier
Sun 12/2811:20 pmSFO - MDW
1 stop12h 01mFrontier
Deal found 11/12$263
This Kiwi.com deal was found by Cheapflights users on 11/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/47:23 pmMDW - SFO
1 stop19h 55mFrontier
Mon 12/86:30 amSFO - MDW
2 stops13h 42mFrontier
Deal found 11/12$264
This Kiwi.com deal was found by Cheapflights users on 11/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/117:23 pmMDW - SFO
1 stop19h 55mFrontier
Thu 12/186:00 amSFO - MDW
2 stops29h 59mFrontier
Deal found 11/12$265
This Kiwi.com deal was found by Cheapflights users on 11/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/266:05 amMDW - SFO
1 stop15h 18mFrontier
Mon 12/16:32 pmSFO - MDW
2 stops12h 45mFrontier
Deal found 11/12$266

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to San Francisco that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated November 13, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to San Francisco that are best for you.

Fly from

Midway

Fly to

San Francisco

Route

Depart

Return

Price

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Sat 12/6

2:45 pm-8:20 pm

1 stop7h 35m

San Francisco

Sat 12/13

10:10 am-4:10 pm

Nonstop4h 00m

$269

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Sat 12/6

9:29 am-2:23 pm

1 stop6h 54m

San Francisco

Sat 12/13

6:00 am-3:44 pm

1 stop7h 44m

$279

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Wed 12/17

1:50 pm-8:28 pm

1 stop8h 38m

San Francisco

Wed 1/7

11:46 am-10:09 pm

1 stop8h 23m

$279

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Mon 12/8

1:14 pm-10:31 pm

2 stops11h 17m

San Francisco

Sun 12/14

12:30 am-9:19 am

1 stop6h 49m

$286

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Thu 11/27

8:15 am-11:00 am

Nonstop4h 45m

San Francisco

Wed 12/3

6:10 am-12:15 pm

Nonstop4h 05m

$288

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Wed 12/10

8:15 am-11:00 am

Nonstop4h 45m

San Francisco

Sat 12/13

5:30 am-4:30 pm

2 stops9h 00m

$289

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Tue 12/9

8:35 am-2:40 pm

2 stops8h 05m

San Francisco

Tue 12/16

10:35 am-8:55 pm

1 stop8h 20m

$299

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Mon 1/19

10:46 am-7:45 pm

1 stop10h 59m

$130

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Fri 1/16

8:15 am-11:15 am

Nonstop5h 00m

$140

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Sun 12/14

8:20 am-11:05 am

Nonstop4h 45m

$140

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/10

Showing 1-10 of 18 results
1
2

Compare providers for flights from Midway to San Francisco

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to San Francisco in November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star
CheapOairPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-San Francisco flights, users find the pricing of CheapOair to be most consistent on Cheapflights vs. CheapOair Users can find the same prices on Chicago Midway Airport-San Francisco flight deals on Cheapflights vs. CheapOair >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-San Francisco flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-San Francisco flights, Cheapflights users trust CheapOair the most. CheapOair has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-San Francisco flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Midway to San Francisco

Have a flexible travel schedule? Discover the best time to fly to San Francisco from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to San Francisco

What is the cheapest month to book a flight from Chicago Midway Airport to San Francisco?

Currently, October is the cheapest month in which you can book a flight from Chicago Midway Airport to San Francisco (average of $145). Flying from Chicago Midway Airport to San Francisco in November is currently the most expensive (average of $307). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from MDW to SFO?

Find hourly flight availability from Midway to San Francisco. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 13, 2025.

It’s typically best to fly out from Chicago Midway Airport to San Francisco in the morning. Doing so could potentially save you 23% on the flight price compared to flying at noon, which is usually more expensive.

Reviews of airlines servicing San Francisco

Get insights into the airlines that provide service to San Francisco. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to San Francisco. Reviews last updated November 13, 2025.
Read reviews from past customers who have flown Southwest, United Airlines, and Frontier from Chicago Midway Airport to San Francisco. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,236 reviews

Entertainment

7.5

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,236 reviews
Southwest
8.0
Very good
4,236 reviews

Entertainment

7.5

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
United Airlines
7.4
Good
9,015 reviews
Southwest
8.0
Very good
4,236 reviews

Entertainment

7.5

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Frontier
5.8
Fair
3,114 reviews
Southwest
8.0
Very good
4,236 reviews

Entertainment

7.5

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

Related info for your journey

Find useful and relevant information for your journey from Midway to San Francisco. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to San Francisco from Chicago Midway?

    Located just 11.8 mi from the city center, San Francisco is the airport most travelers will use when flying to San Francisco from Chicago Midway. Booking flights from Chicago Midway to San Francisco (SFO) should be relatively easy as there is 1 daily inbound flight from Chicago Midway from 3 different airlines.

  • How long is the flight from Chicago Midway Airport to San Francisco?

    There are many flights that can get you from Chicago Midway Airport to San Francisco in 6h 54m. Fly via Southwest or Delta to get the fastest option. The distance between Chicago Midway Airport and San Francisco is about 1849 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines flying from Chicago Midway Airport to San Francisco round-trip?

    According to our current data, Frontier ($90), United Airlines ($217), and Southwest ($227) offers the cheapest pricing from Chicago Midway Airport to San Francisco. You may be able to fly from Chicago Midway Airport to San Francisco for 77% less than the average price by searching for these airlines.

  • What are the cheapest flights from Chicago Midway Airport to San Francisco?

    Looking at all options, your cheapest flight can be booked for $134. While the most popular route (Chicago Midway - San Francisco) can be booked for $130 on average, our data indicates $366 when flying from Chicago Midway Airport to San Francisco.

  • Can I find deals for flights from Midway to San Francisco that include hotel bookings?

    Yes. In addition to deals on Midway to San Francisco flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to San Francisco?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to San Francisco.

  • Can I find deals for business class flights from Midway to San Francisco?

    Yes. Cheapflights offers flight deals from Midway to San Francisco by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago Midway Airport to San Francisco?

    Currently, October is the cheapest month in which you can book a flight from Chicago Midway Airport to San Francisco (average of $145). Flying from Chicago Midway Airport to San Francisco in November is currently the most expensive (average of $307). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near San Francisco?

Book flights to San Francisco if you plan to visit one of these locations
Roseville
South San Francisco
Santa Cruz
Livermore
Turlock
Manteca
Watsonville
Sunnyvale
Santa Clara
Vallejo
Hollister
San Bruno
Foster City
Redwood City
Union City
Burlingame
Lodi
San Mateo
Vacaville
Lathrop

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Alternative routes for Midway to San Francisco

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Top 3 airlines flying from Midway to San Francisco

Discover the top 3 airlines that operate flights from Midway to San Francisco. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated November 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$90Average$313FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$217Average$418FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$227Average$457FlexibilityNo cancel feeOn-time63%

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