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$127+ Cheap flights from San Francisco (SFO) to Midway (MDW)

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 1/22. Fares are subject to change and may not be available on all flights or dates of travel.
SFO — MDW
Dec 26 — Jan 21
Fri 12/26
Fri 1/2
1 adult, Economy
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Cheapflights Tip: The best prices from San Francisco to Chicago Midway are usually found in January or February, booked 33 days in advance, depart on a Tuesday or Wednesday and return on a Saturday

Cheap flight deals from San Francisco to Midway

Discover tips and strategies to find the most affordable flight options for your journey from San Francisco (SFO) to Midway (MDW). 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 26, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$283
(Southwest)

One-way from

$127
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$442

Good round-trip deal

$342 or less

Good one-way deal

$168 or less
Provider with most accurate pricing for San Francisco-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for San Francisco-Chicago Midway flights.
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From San Francisco to Chicago Midway
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One-way flight from San Francisco to Chicago Midway
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($13 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($12 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 San Francisco to Chicago Midway.
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Price to beat on a one-way flight from San Francisco to Chicago Midway.
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Find flight deals from San Francisco to Midway

Cheapest flights from San Francisco to Midway
Explore the most affordable flight options available from San Francisco to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 26, 2025.

This Southwest deal was found by Cheapflights users on 11/25. 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.
Wed 12/106:10 amSFO - MDW
Nonstop4h 05mSouthwest
Wed 12/178:20 amMDW - SFO
1 stop8h 45mSouthwest
Deal found 11/25$283
This Kiwi.com deal was found by Cheapflights users on 11/25. 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 12/118:43 amSFO - MDW
2 stops11h 29mFrontier
Sun 12/147:24 pmMDW - SFO
1 stop24h 10mFrontier
Deal found 11/25$285
This Delta deal was found by Cheapflights users on 11/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/255:50 amSFO - MDW
1 stop9h 36mDelta
Tue 1/66:14 pmMDW - SFO
1 stop7h 11mDelta
Deal found 11/25$288
This CheapOair deal was found by Cheapflights users on 11/25. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/511:38 pmSFO - MDW
1 stop12h 21mFrontier
Sun 12/76:15 amMDW - SFO
1 stop9h 03mFrontier
Deal found 11/25$292
This Southwest deal was found by Cheapflights users on 11/25. 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.
Mon 12/221:55 pmSFO - MDW
1 stop9h 00mSouthwest
Sat 1/178:25 amMDW - SFO
1 stop8h 20mSouthwest
Deal found 11/25$295
This Kiwi.com deal was found by Cheapflights users on 11/25. 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.
Tue 12/231:29 pmSFO - MDW
2 stops29h 16mFrontier
Thu 12/256:12 amMDW - SFO
1 stop9h 01mFrontier
Deal found 11/25$296
This Southwest deal was found by Cheapflights users on 11/24. 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.
Mon 12/156:10 amSFO - MDW
Nonstop4h 05mSouthwest
Thu 12/188:20 amMDW - SFO
Nonstop4h 45mSouthwest
Deal found 11/24$297
This Kiwi.com deal was found by Cheapflights users on 11/25. 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 12/116:30 amSFO - MDW
2 stops13h 42mFrontier
Mon 12/156:15 amMDW - SFO
1 stop13h 19mFrontier
Deal found 11/25$298
This Southwest deal was found by Cheapflights users on 11/25. 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.
Tue 12/96:10 amSFO - MDW
Nonstop4h 05mSouthwest
Sat 12/131:15 pmMDW - SFO
1 stop8h 50mSouthwest
Deal found 11/25$305

Cheapflights Fare Finder

 
Customize your flight search to find flights from San Francisco to Midway 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 26, 2025.
Use the filters below to find and compare flights from San Francisco to Chicago Midway Airport that are best for you.

Fly from

San Francisco

Fly to

Midway

Route

Depart

Return

Price

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Thu 12/25

5:50 am-5:26 pm

1 stop9h 36m

Chicago Midway

Tue 1/6

6:14 pm-11:25 pm

1 stop7h 11m

$288

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Mon 12/22

8:40 am-6:55 pm

1 stop8h 15m

Chicago Midway

Sat 1/17

7:00 am-2:45 pm

2 stops9h 45m

$300

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Sun 1/11

12:40 am-9:08 am

1 stop6h 28m

Chicago Midway

Thu 1/15

1:28 pm-6:38 pm

1 stop7h 10m

$305

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Fri 12/12

12:30 am-9:19 am

1 stop6h 49m

Chicago Midway

Tue 1/6

6:14 pm-11:25 pm

1 stop7h 11m

$307

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Thu 1/8

12:40 am-9:08 am

1 stop6h 28m

Chicago Midway

Fri 1/16

7:16 pm-11:47 pm

1 stop6h 31m

$313

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Fri 2/13

5:55 am-11:55 am

Nonstop4h 00m

Chicago Midway

Mon 2/16

7:55 am-10:55 am

Nonstop5h 00m

$315

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Wed 4/1

5:40 am-11:40 am

Nonstop4h 00m

Chicago Midway

Wed 4/1

9:05 pm-11:45 pm

Nonstop4h 40m

$315

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Thu 1/1

5:30 am-1:40 pm

1 stop6h 10m

Chicago Midway

Wed 1/7

10:05 am-2:55 pm

1 stop6h 50m

$320

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Wed 12/31

12:10 am-11:06 am

1 stop8h 56m

Chicago Midway

Wed 1/7

9:32 am-5:49 pm

2 stops10h 17m

$332

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Fri 4/17

9:30 pm-9:51 am

1 stop10h 21m

Chicago Midway

Mon 4/20

5:25 pm-12:15 am

1 stop8h 50m

$333

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/25

Showing 1-10 of 20 results
1
2

Compare providers for flights from San Francisco to Midway

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 San Francisco to Midway in November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
OvagoPrice Accuracy2 starsTrust Score*2 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 San Francisco-Chicago Midway Airport flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on San Francisco-Chicago Midway Airport flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from San Francisco-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on San Francisco-Chicago Midway Airport flights, Cheapflights users trust eDreams the most. eDreams 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 San Francisco-Chicago Midway Airport 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 San Francisco to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from San Francisco 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 San Francisco to Chicago Midway Airport

How far ahead should I book a flight from San Francisco to Chicago Midway Airport?

Use this chart to determine the optimal time to book a round-trip flight from San Francisco to Midway. Price data was last updated on November 21, 2025.

The best time to book flights from San Francisco to Chicago Midway Airport is 33 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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

Currently, January is the cheapest month in which you can book a flight from San Francisco to Chicago Midway Airport (average of $148). Flying from San Francisco to Chicago Midway Airport in June is currently the most expensive (average of $242). 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 SFO to MDW?

Find hourly flight availability from San Francisco to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 26, 2025.

It’s typically best to fly out from San Francisco to Chicago Midway Airport in the afternoon. Doing so could potentially save you 50% on the flight price compared to flying in the evening, which is usually more expensive.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated November 26, 2025.
Read through reviews of airlines operating flights from San Francisco to Chicago Midway Airport, such as Southwest, Delta, and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,254 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

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
4,254 reviews
Southwest
8.0
Very good
4,254 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

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.
Delta
7.9
Good
7,999 reviews
Southwest
8.0
Very good
4,254 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

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
9,046 reviews
Southwest
8.0
Very good
4,254 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

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.
American Airlines
7.2
Good
11,038 reviews
Southwest
8.0
Very good
4,254 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

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
3,099 reviews
Southwest
8.0
Very good
4,254 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

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 San Francisco to Midway. 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 from for flights from San Francisco to Chicago Midway?

    San Francisco (SFO), located 11.8 mi from the city center, is the airport you fly out of when you book flights from San Francisco to Chicago Midway. 5 airlines have flights from San Francisco to Chicago Midway on a regular basis. Booking flights from San Francisco to Chicago Midway should not be difficult; the airport handles an average of 0 outbound flights to Chicago Midway per day.

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

    Delta and Southwest can get you from San Francisco to Chicago Midway Airport in just under 8h 15m. Your travel time can differ by up to 1h 21m. The distance from San Francisco to Chicago Midway Airport is about 1849 mi. This flight may include one or multiple stops.

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

    Cheapflights users have booked flights from San Francisco to Chicago Midway Airport round-trip from $133. Other airlines that can offer you cheap pricing are Frontier, from $147, and American Airlines, from $197. These flights start at 63% lower than the current average price 3 months from now.

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

    On average you can expect to pay $352 for a flight from San Francisco to Chicago Midway Airport. The cheapest flight overall is $98 while the most popular route, (San Francisco - Chicago Midway) is currently priced at $207.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from San Francisco to Midway 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 San Francisco to Chicago Midway Airport?

    Currently, January is the cheapest month in which you can book a flight from San Francisco to Chicago Midway Airport (average of $148). Flying from San Francisco to Chicago Midway Airport in June is currently the most expensive (average of $242). 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from San Francisco to Midway

Discover the top 5 airlines that operate flights from San Francisco to Midway. 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 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$133Average$407FlexibilityNo cancel feeOn-time69%
FrontierCheapest$147Average$237FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$197Average$332FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$217Average$399FlexibilityNo cancel feeOn-time63%
DeltaCheapest$256Average$338FlexibilityNo cancel feeOn-timeN/A

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