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$102+ 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 11/10. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SFO
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago Midway to San Francisco are usually found in November or September, booked 24 days in advance, depart on a Thursday or Wednesday and return on a Wednesday

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 September 11, 2025.

Round-trip from

$212
(Southwest)

One-way from

$102
(Kiwi.com)

Popular in

December

Cheapest in

November

Average price

$309

Good round-trip deal

$333 or less

Good one-way deal

$191 or less
From Chicago Midway to San Francisco
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One-way flight from Chicago Midway to San Francisco
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High demand for flights, 0% potential price rise
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Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 11, 2025.

This Southwest deal was found by Cheapflights users on 9/10. 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.
Tue 9/308:30 amMDW - SFO
2 stops8h 10mSouthwest
Tue 10/73:00 pmSFO - MDW
1 stop7h 25mSouthwest
Deal found 9/10$212
This Southwest deal was found by Cheapflights users on 9/11. 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.
Thu 10/23:10 pmMDW - SFO
1 stop6h 35mSouthwest
Tue 10/75:45 amSFO - MDW
1 stop7h 30mSouthwest
Deal found 9/11$213
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/910:30 amMDW - SFO
2 stops15h 39mFrontier
Sun 10/128:21 pmSFO - MDW
1 stop11h 10mFrontier
Deal found 9/10$214
This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
Thu 10/21:53 pmMDW - SFO
1 stop7h 15mMultiple Airlines
Tue 10/78:00 amSFO - MDW
2 stops13h 20mMultiple Airlines
Deal found 9/11$216
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/26:30 amMDW - SFO
2 stops13h 37mFrontier
Sun 10/511:57 pmSFO - MDW
1 stop11h 14mFrontier
Deal found 9/10$217
This CheapOair deal was found by Cheapflights users on 9/10. 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.
Fri 9/265:15 pmMDW - SFO
1 stop30h 06mFrontier
Sat 10/1110:23 pmSFO - MDW
1 stop23h 23mFrontier
Deal found 9/10$218
This Southwest deal was found by Cheapflights users on 9/11. 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 10/45:05 pmMDW - SFO
1 stop6h 25mSouthwest
Sat 10/1110:55 amSFO - MDW
1 stop9h 40mSouthwest
Deal found 9/11$219
This Frontier deal was found by Cheapflights users on 9/10. 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.
Fri 9/193:48 pmMDW - SFO
1 stop10h 28mFrontier
Sun 10/511:57 pmSFO - MDW
1 stop11h 14mFrontier
Deal found 9/10$220
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/37:15 amMDW - SFO
2 stops16h 06mFrontier
Sun 10/511:57 pmSFO - MDW
1 stop11h 14mFrontier
Deal found 9/10$221
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/34:48 pmMDW - SFO
1 stop9h 28mMultiple Airlines
Tue 10/78:00 amSFO - MDW
2 stops13h 20mMultiple Airlines
Deal found 9/10$222
This CheapOair deal was found by Cheapflights users on 9/10. 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.
Thu 10/210:13 amMDW - SFO
1 stop14h 49mFrontier
Sat 10/410:49 amSFO - MDW
2 stops20h 34mFrontier
Deal found 9/10$223
This CheapOair deal was found by Cheapflights users on 9/10. 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.
Thu 10/3012:30 pmMDW - SFO
1 stop13h 44mFrontier
Sun 11/28:09 pmSFO - MDW
2 stops19h 06mFrontier
Deal found 9/10$224

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 September 11, 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

Wed 10/29

5:30 pm-11:05 pm

2 stops7h 35m

San Francisco

Sun 11/2

5:15 am-11:20 am

Nonstop4h 05m

$218

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Sat 10/4

5:05 pm-9:30 pm

1 stop6h 25m

San Francisco

Sat 10/11

10:55 am-10:35 pm

1 stop9h 40m

$219

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Thu 10/30

12:55 pm-3:25 pm

Nonstop4h 30m

San Francisco

Sun 11/2

5:15 am-11:20 am

Nonstop4h 05m

$239

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Wed 10/29

2:45 pm-5:15 pm

Nonstop4h 30m

San Francisco

Tue 11/11

6:10 am-12:15 pm

Nonstop4h 05m

$241

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Sat 10/25

5:15 pm-9:25 pm

1 stop6h 10m

San Francisco

Mon 11/3

9:25 pm-10:10 am

1 stop10h 45m

$242

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Mon 10/27

10:56 pm-5:43 pm

1 stop20h 47m

San Francisco

Mon 11/3

6:34 am-10:11 pm

2 stops13h 37m

$246

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Thu 11/6

6:45 am-2:20 pm

1 stop9h 35m

San Francisco

Sun 11/9

6:10 am-12:15 pm

Nonstop4h 05m

$249

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Sat 10/4

1:08 pm-5:47 pm

1 stop6h 39m

San Francisco

Mon 10/6

12:35 am-8:55 am

1 stop6h 20m

$257

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Sat 10/18

1:11 pm-5:51 pm

1 stop6h 40m

San Francisco

Wed 10/22

12:35 am-8:55 am

1 stop6h 20m

$257

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Sat 10/25

4:23 pm-10:30 pm

1 stop8h 07m

San Francisco

Mon 10/27

12:35 am-8:55 am

1 stop6h 20m

$257

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 23 results
1
2
3

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

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

Use this chart to determine the optimal time to book a round-trip flight from Midway to San Francisco. Price data was last updated on August 29, 2025.

The best time to book flights from Chicago Midway Airport to San Francisco is 23 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 Chicago Midway Airport to San Francisco?

Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to San Francisco (average of $276). Flying from Chicago Midway Airport to San Francisco in June is currently the most expensive (average of $357). 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 September 11, 2025.

It’s typically best to fly out from Chicago Midway Airport to San Francisco in the morning. Doing so could potentially save you 19% 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 September 7, 2025.

Travelers seeking maximum savings on their Chicago Midway Airport to San Francisco flight should consider departing on Wednesday 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 September 11, 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
4,248 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

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
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

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
8,937 reviews
Southwest
8.0
Very good
4,248 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

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
3,177 reviews
Southwest
8.0
Very good
4,248 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

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 7h 35m. Fly via Southwest 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 ($150), 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 62% 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 $98. While the most popular route (Chicago Midway - San Francisco) can be booked for $165 on average, our data indicates $399 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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to San Francisco (average of $276). Flying from Chicago Midway Airport to San Francisco in June is currently the most expensive (average of $357). 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
Santa Cruz
Livermore
South San Francisco
Turlock
Antioch
Watsonville
Manteca
Santa Clara
Sunnyvale
Hollister
Vacaville
Foster City
Vallejo
Burlingame
Redwood City
Union City
San Leandro
San Mateo
Lathrop

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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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$150Average$320FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$217Average$418FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$227Average$440FlexibilityNo cancel feeOn-time63%

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