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$125+ 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 3/7. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SFO
Feb 25 — Mar 41
Wed 2/25
Wed 3/4
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 January 26, 2026.

This Southwest deal was found by Cheapflights users on 1/24. 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 2/144:40 pm
MDW
-
SFO
1 stop7h 15m
Southwest
Tue 2/176:25 am
SFO
-
MDW
Nonstop4h 00m
Southwest
Deal found 1/24$241
This Southwest deal was found by Cheapflights users on 1/25. 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 3/146:20 pm
MDW
-
SFO
1 stop6h 55m
Southwest
Sat 3/215:15 am
SFO
-
MDW
Nonstop3h 55m
Southwest
Deal found 1/25$242
This Southwest deal was found by Cheapflights users on 1/25. 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 3/149:40 pm
MDW
-
SFO
Nonstop4h 40m
Southwest
Wed 3/1810:55 pm
SFO
-
MDW
1 stop8h 25m
Southwest
Deal found 1/25$244
This Southwest deal was found by Cheapflights users on 1/25. 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 3/710:15 am
MDW
-
SFO
2 stops9h 00m
Southwest
Sat 3/1411:25 pm
SFO
-
MDW
Nonstop4h 05m
Southwest
Deal found 1/25$246
This Southwest deal was found by Cheapflights users on 1/25. 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.
Thu 2/267:55 am
MDW
-
SFO
Nonstop5h 00m
Southwest
Sat 2/286:55 am
SFO
-
MDW
Nonstop4h 00m
Southwest
Deal found 1/25$248
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 3/57:30 am
MDW
-
SFO
1 stop16h 09m
Frontier
Mon 3/99:24 pm
SFO
-
MDW
2 stops35h 01m
Frontier
Deal found 1/25$249
This Southwest deal was found by Cheapflights users on 1/25. 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 3/149:40 pm
MDW
-
SFO
Nonstop4h 40m
Southwest
Fri 3/2011:25 pm
SFO
-
MDW
Nonstop4h 05m
Southwest
Deal found 1/25$250
This Kiwi.com deal was found by Cheapflights users on 1/25. 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.
Fri 2/277:32 pm
MDW
-
SFO
1 stop24h 26m
Frontier
Mon 3/23:18 pm
SFO
-
MDW
1 stop6h 36m
Frontier
Deal found 1/25$253
This Southwest deal was found by Cheapflights users on 1/24. 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 2/144:40 pm
MDW
-
SFO
1 stop7h 15m
Southwest
Sat 2/216:40 am
SFO
-
MDW
2 stops8h 20m
Southwest
Deal found 1/24$254
This Southwest deal was found by Cheapflights users on 1/25. 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 4/43:05 pm
MDW
-
SFO
2 stops11h 05m
Southwest
Sat 4/117:00 am
SFO
-
MDW
1 stop10h 20m
Southwest
Deal found 1/25$255

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 January 26, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$241
(Southwest)

One-way from

$125
(Expedia)

Popular in

December

Cheapest in

October

Average price

$431

Good round-trip deal

$283 or less

Good one-way deal

$158 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. 8% potential increase in price ($38 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 26, 2026.
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 2/14

4:40 pm-9:55 pm

1 stop7h 15m

San Francisco

Tue 2/17

6:25 am-12:25 pm

Nonstop4h 00m

$241

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Sat 3/14

9:40 pm-12:20 am

Nonstop4h 40m

San Francisco

Sat 3/21

5:15 am-11:10 am

Nonstop3h 55m

$252

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Wed 3/4

10:49 am-5:48 pm

1 stop8h 59m

San Francisco

Mon 3/9

9:35 pm-9:56 am

1 stop10h 21m

$262

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Mon 4/6

1:10 pm-7:07 pm

1 stop7h 57m

San Francisco

Wed 4/15

10:35 pm-9:56 am

1 stop9h 21m

$264

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Wed 3/4

4:10 pm-9:50 pm

1 stop7h 40m

San Francisco

Wed 3/11

11:25 pm-5:30 am

Nonstop4h 05m

$265

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Sat 3/21

9:40 pm-12:20 am

Nonstop4h 40m

San Francisco

Mon 3/23

11:25 pm-5:30 am

Nonstop4h 05m

$279

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Wed 3/18

5:45 am-11:45 am

1 stop8h 00m

San Francisco

Wed 3/25

5:55 am-4:10 pm

2 stops8h 15m

$282

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Tue 3/31

7:05 am-1:50 pm

1 stop8h 45m

San Francisco

Mon 4/13

11:25 pm-5:40 am

Nonstop4h 15m

$282

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Thu 4/23

9:45 pm-12:20 am

Nonstop4h 35m

San Francisco

Wed 4/29

7:40 pm-4:35 am

1 stop6h 55m

$282

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Sat 2/28

2:05 pm-10:05 pm

2 stops10h 00m

San Francisco

Sat 3/7

5:00 am-5:40 pm

2 stops10h 40m

$285

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/24

Showing 1-10 of 20 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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star
CheapOairPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-San Francisco flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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 January 26, 2026.

It’s typically best to fly out from Chicago Midway Airport to San Francisco in the evening. Doing so could potentially save you 29% 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 January 24, 2026.

Travelers seeking maximum savings on their Chicago Midway Airport to San Francisco flight should consider departing on Tuesday afternoons 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 January 26, 2026.
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
4,268 reviews

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Overall

8.0

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
8.0
Very good
4,268 reviews
Southwest
8.0
Very good
4,268 reviews

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Overall

8.0

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
9,199 reviews
Southwest
8.0
Very good
4,268 reviews

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Overall

8.0

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
5.7
Fair
3,058 reviews
Southwest
8.0
Very good
4,268 reviews

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Overall

8.0

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 15m. 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 ($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 $98. 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 $108. While the most popular route (Chicago Midway - San Francisco) can be booked for $222 on average, our data indicates $243 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
South San Francisco
Santa Cruz
Roseville
Santa Clara
Livermore
Watsonville
San Bruno
Daly City
Sunnyvale
Turlock
Vacaville
San Carlos
San Ramon
Manteca
Vallejo
San Lorenzo
Davis
Hollister
Redwood City
Union City

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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 January 26, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$90Average$217FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$217Average$418FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$217Average$442FlexibilityNo cancel feeOn-time63%

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