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San Francisco Bay Area

$79+ Cheap flights from Midway (MDW) to San Francisco Bay Area

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 9/29. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SFO
Aug 18 — Aug 251
Mon 8/18
Mon 8/25
1 adult, Economy
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Cheap flight deals from Midway to San Francisco Bay Area

Keep the following information in mind while searching for Midway to San Francisco Bay Area flight deals. Data was last updated August 13, 2025.

Round-trip from

$173
(Southwest)

One-way from

$79
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$317
From Chicago Midway to San Francisco Bay Area
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One-way flight from Chicago Midway to San Francisco Bay Area
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Highest demand for flights based on searches. 7% potential increase in price ($26 potential increase over avg. RT price).
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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 August 2025
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Find flight deals from Midway to San Francisco Bay Area

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

This Southwest deal was found by Cheapflights users on 8/11. 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.
Tue 9/165:40 pmMDW - SJC
Nonstop4h 30mSouthwest
Tue 9/236:35 amSJC - MDW
Nonstop4h 10mSouthwest
Deal found 8/11$173
This Southwest deal was found by Cheapflights users on 8/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/105:40 pmMDW - SJC
Nonstop4h 30mSouthwest
Sun 9/147:00 amSJC - MDW
Nonstop4h 05mSouthwest
Deal found 8/12$190
This Southwest deal was found by Cheapflights users on 8/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/117:55 pmMDW - SJC
Nonstop4h 30mSouthwest
Sun 9/147:00 amSJC - MDW
Nonstop4h 05mSouthwest
Deal found 8/12$207
This Southwest deal was found by Cheapflights users on 8/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/312:55 pmMDW - SFO
Nonstop4h 30mSouthwest
Wed 10/86:30 amSFO - MDW
Nonstop4h 05mSouthwest
Deal found 8/12$207
This Southwest deal was found by Cheapflights users on 8/11. 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 10/21:20 pmMDW - SJC
1 stop7h 05mSouthwest
Sun 10/56:35 amSJC - MDW
Nonstop4h 10mSouthwest
Deal found 8/11$217
This Southwest deal was found by Cheapflights users on 8/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/241:35 pmMDW - SFO
1 stop9h 00mSouthwest
Sun 9/286:20 amSFO - MDW
1 stop6h 40mSouthwest
Deal found 8/12$227
This Southwest deal was found by Cheapflights users on 8/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/206:20 amMDW - SFO
1 stop9h 35mSouthwest
Thu 11/276:15 amSFO - MDW
Nonstop4h 05mSouthwest
Deal found 8/12$232
This Priceline deal was found by Cheapflights users on 8/12. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/166:24 pmMDW - SFO
1 stop7h 50mFrontier
Mon 10/2012:19 pmSFO - MDW
1 stop10h 05mFrontier
Deal found 8/12$235
This Southwest deal was found by Cheapflights users on 8/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/93:50 pmMDW - SFO
Nonstop4h 35mSouthwest
Tue 9/1610:45 amSFO - MDW
Nonstop4h 10mSouthwest
Deal found 8/12$236
This Southwest deal was found by Cheapflights users on 8/11. 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.
Fri 9/265:25 amMDW - SFO
1 stop6h 00mSouthwest
Sun 9/286:20 amSFO - MDW
1 stop6h 40mSouthwest
Deal found 8/11$237
This Priceline deal was found by Cheapflights users on 8/11. 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.
Thu 9/181:53 pmMDW - SFO
1 stop7h 15mFrontier
Mon 9/226:29 amSFO - MDW
1 stop7h 24mFrontier
Deal found 8/11$238
This Southwest deal was found by Cheapflights users on 8/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/33:50 pmMDW - SFO
Nonstop4h 35mSouthwest
Wed 9/108:35 amSFO - MDW
1 stop5h 55mSouthwest
Deal found 8/12$241

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to San Francisco Bay Area 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 August 13, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to San Francisco Bay Area that are best for you.

Fly from

Midway

Fly to

San Francisco Bay Area

Route

Depart

Return

Price

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Tue 9/16

5:40 pm-8:10 pm

Nonstop4h 30m

San Jose

Tue 9/23

6:35 am-12:45 pm

Nonstop4h 10m

$173

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Wed 9/10

5:40 pm-8:10 pm

Nonstop4h 30m

San Jose

Sun 9/14

7:00 am-1:05 pm

Nonstop4h 05m

$190

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Thu 9/18

7:55 pm-10:25 pm

Nonstop4h 30m

San Jose

Tue 9/23

6:35 am-12:45 pm

Nonstop4h 10m

$190

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Wed 10/22

4:35 pm-9:20 pm

1 stop6h 45m

San Jose

Sun 10/26

6:35 am-12:45 pm

Nonstop4h 10m

$200

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Sat 11/8

8:15 am-11:00 am

Nonstop4h 45m

San Francisco

Wed 11/12

2:15 pm-10:15 pm

1 stop6h 00m

$207

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Sat 10/25

8:15 am-10:50 am

Nonstop4h 35m

San Francisco

Sun 11/2

5:15 am-11:20 am

Nonstop4h 05m

$207

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Wed 10/22

2:45 pm-5:15 pm

Nonstop4h 30m

San Francisco

Mon 10/27

6:00 am-12:05 pm

Nonstop4h 05m

$207

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Tue 10/7

2:45 pm-5:15 pm

Nonstop4h 30m

San Francisco

Sun 10/12

6:00 am-12:05 pm

Nonstop4h 05m

$207

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Wed 10/22

2:45 pm-5:15 pm

Nonstop4h 30m

San Francisco

Sun 10/26

6:00 am-12:05 pm

Nonstop4h 05m

$207

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Fri 10/3

12:55 pm-3:25 pm

Nonstop4h 30m

San Francisco

Wed 10/8

6:30 am-12:35 pm

Nonstop4h 05m

$207

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/11

Showing 1-10 of 49 results
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Best time to book a flight from Midway to San Francisco Bay Area

Have a flexible travel schedule? Discover the best time to fly to San Francisco Bay Area 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 Bay Area

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

Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to San Francisco Bay Area (average of $276). Flying from Chicago Midway Airport to San Francisco Bay Area in June is currently the most expensive (average of $358). 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 XIH?

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

When flying from Chicago Midway Airport to San Francisco Bay Area, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Reviews of airlines servicing San Francisco Bay Area

Get insights into the airlines that provide service to San Francisco Bay Area. 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 Bay Area. Reviews last updated August 13, 2025.
Read reviews from past customers who have flown Southwest, United Airlines, and Frontier from Chicago Midway Airport to San Francisco Bay Area. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Overall

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
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Overall

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
8,920 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Overall

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
3,221 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Overall

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 Bay Area. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the most popular routes from Chicago Midway Airport to San Francisco Bay Area?

    Most travelers choose Chicago Midway - San Francisco, Chicago Midway - Oakland or Chicago Midway - San Jose when deciding on the best route from Chicago Midway Airport to San Francisco Bay Area.

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

    Looking for the cheapest flight from Chicago Midway Airport to San Francisco Bay Area? While on average our users pay $188, our data indicates the cheapest price to be $98. The most popular route (Chicago Midway - San Francisco), is priced around $188.

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

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

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

    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 Bay Area.

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

    Yes. Cheapflights offers flight deals from Midway to San Francisco Bay Area 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 Bay Area?

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to San Francisco Bay Area (average of $276). Flying from Chicago Midway Airport to San Francisco Bay Area in June is currently the most expensive (average of $358). 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

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Alternative routes for Midway to San Francisco Bay Area

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Midway to San Francisco Bay Area

Discover the top 3 airlines that operate flights from Midway to San Francisco Bay Area. 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 August 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$118Average$282FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$141Average$357FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$237Average$421FlexibilityNo cancel feeOn-time63%

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