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$126+ 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 3/6. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SFO
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheap 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 December 12, 2025.

This Frontier deal was found by Cheapflights users on 12/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/2311:29 amMDW - SFO
1 stop9h 48mFrontier
Fri 1/96:05 amSFO - MDW
1 stop6h 00mFrontier
Deal found 12/10$288
This Frontier deal was found by Cheapflights users on 12/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/2311:29 amMDW - SFO
1 stop9h 48mFrontier
Sat 1/1011:20 pmSFO - MDW
1 stop10h 11mFrontier
Deal found 12/10$304
This Delta deal was found by Cheapflights users on 12/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/259:29 amMDW - SFO
1 stop7h 10mDelta
Sun 1/412:40 amSFO - MDW
1 stop6h 28mDelta
Deal found 12/11$309
This CheapOair deal was found by Cheapflights users on 12/11. 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 CheapOair 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
Mon 1/126:05 amSFO - MDW
1 stop6h 00mFrontier
Deal found 12/11$313
This CheapOair deal was found by Cheapflights users on 12/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/236:14 amMDW - SFO
1 stop8h 59mFrontier
Thu 1/111:20 pmSFO - MDW
1 stop12h 01mFrontier
Deal found 12/10$325
This Frontier deal was found by Cheapflights users on 12/9. 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 12/213:01 pmMDW - SFO
1 stop8h 00mFrontier
Tue 12/306:24 amSFO - MDW
1 stop11h 31mFrontier
Deal found 12/9$333
This Frontier deal was found by Cheapflights users on 12/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:12 amMDW - SFO
1 stop9h 01mFrontier
Fri 1/96:05 amSFO - MDW
1 stop6h 00mFrontier
Deal found 12/10$347
This Priceline deal was found by Cheapflights users on 12/11. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:12 amMDW - SFO
1 stop9h 01mFrontier
Tue 12/308:16 pmSFO - MDW
1 stop11h 05mFrontier
Deal found 12/11$363
This Delta deal was found by Cheapflights users on 12/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/249:50 amMDW - SFO
1 stop10h 09mDelta
Wed 1/710:54 pmSFO - MDW
1 stop7h 58mDelta
Deal found 12/11$368
This CheapOair deal was found by Cheapflights users on 12/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:12 amMDW - SFO
1 stop9h 01mFrontier
Sun 12/286:24 amSFO - MDW
1 stop13h 26mFrontier
Deal found 12/10$384
This Southwest deal was found by Cheapflights users on 12/9. 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.
Wed 12/245:15 amMDW - SFO
1 stop6h 55mSouthwest
Wed 12/316:10 amSFO - MDW
Nonstop4h 05mSouthwest
Deal found 12/9$386

Find 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 December 12, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$238
(Trip.com)

One-way from

$126
(Frontier)

Popular in

December

Cheapest in

October

Average price

$506

Good round-trip deal

$537 or less

Good one-way deal

$193 or less
Provider with most accurate pricing for Chicago Midway-San Francisco flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-San Francisco flights.
Search Deals
From Chicago Midway to San Francisco
Search Deals
One-way flight from Chicago Midway to San Francisco
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($34 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Chicago Midway to San Francisco.
Search Deals
Price to beat on a one-way flight from Chicago Midway to San Francisco.
Search Deals

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 December 12, 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

Thu 1/8

6:14 pm-11:25 pm

1 stop7h 11m

San Francisco

Sun 1/11

5:45 am-5:37 pm

1 stop9h 52m

$259

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Thu 1/22

10:48 am-5:43 pm

1 stop8h 55m

San Francisco

Sun 1/25

10:54 pm-8:52 am

1 stop7h 58m

$259

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Thu 1/8

1:28 pm-6:38 pm

1 stop7h 10m

San Francisco

Thu 1/8

10:54 pm-8:52 am

1 stop7h 58m

$259

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Sun 2/15

1:28 pm-10:41 pm

2 stops11h 13m

San Francisco

Wed 2/18

10:54 pm-8:53 am

1 stop7h 59m

$265

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Fri 1/16

7:16 pm-11:47 pm

1 stop6h 31m

San Francisco

Wed 1/21

6:00 am-5:29 pm

1 stop9h 29m

$275

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Fri 1/9

7:16 pm-11:47 pm

1 stop6h 31m

San Francisco

Wed 1/14

10:54 pm-8:52 am

1 stop7h 58m

$275

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Sat 1/10

8:15 am-11:15 am

Nonstop5h 00m

San Francisco

Mon 1/12

11:10 am-9:15 pm

1 stop8h 05m

$277

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Thu 1/15

3:25 pm-10:05 pm

1 stop8h 40m

San Francisco

Tue 1/20

9:30 pm-9:05 am

1 stop9h 35m

$295

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Thu 1/22

4:10 pm-9:50 pm

1 stop7h 40m

San Francisco

Tue 1/27

8:15 am-6:50 pm

2 stops8h 35m

$298

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Fri 1/9

9:32 am-5:49 pm

2 stops10h 17m

San Francisco

Fri 1/9

12:40 am-11:05 am

1 stop8h 25m

$305

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/11

Showing 1-10 of 22 results
1
2
3

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 December.
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 $332). 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 December 12, 2025.

It’s typically best to fly out from Chicago Midway Airport to San Francisco in the morning. Doing so could potentially save you 28% on the flight price compared to flying at noon, which is usually more expensive.

What is the cheapest day to fly from Chicago Midway Airport to San Francisco?

Use this chart to determine the cheapest time to fly round-trip from Midway to San Francisco. Price data was last updated on December 6, 2025.

Travelers seeking maximum savings on their Chicago Midway Airport to San Francisco flight should consider departing on Thursday evenings when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

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 December 12, 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
7.9
Good
4,252 reviews

Boarding

8.1

Overall

7.9

Comfort

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

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
7.9
Good
4,252 reviews
Southwest
7.9
Good
4,252 reviews

Boarding

8.1

Overall

7.9

Comfort

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

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
9,095 reviews
Southwest
7.9
Good
4,252 reviews

Boarding

8.1

Overall

7.9

Comfort

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

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
3,084 reviews
Southwest
7.9
Good
4,252 reviews

Boarding

8.1

Overall

7.9

Comfort

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

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 are 0 daily inbound flights 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 7h 11m. Fly via Delta to get the fastest option. The distance between Chicago Midway Airport and San Francisco is about 1849 mi.

  • 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 ($217) 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 airlines to fly from Chicago Midway Airport to San Francisco one-way?

    The cheapest airline one-way is Frontier, with whom users have recently found tickets for as low as $96. However, be on the lookout for offers from Southwest and Delta, as they are both options that can get you from Chicago Midway Airport to San Francisco for a low price.

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

    Looking at all options, your cheapest flight can be booked for $119. While the most popular route (Chicago Midway - San Francisco) can be booked for $210 on average, our data indicates $452 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 $332). 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
San Bruno
Redwood City
Daly City
Vallejo
Hollister
Foster City
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Davis
San Ramon
Burlingame
Milpitas

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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 December 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$90Average$217FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$217Average$418FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$217Average$446FlexibilityNo cancel feeOn-time63%

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