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$87+ 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 10/30. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SFO
Oct 29 — Nov 51
Wed 10/29
Wed 11/5
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 September 29, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$217
(Gotogate)

One-way from

$87
(Booking.com)

Popular in

December

Cheapest in

July

Average price

$299
Provider with most accurate pricing for Chicago (CHI)-San Francisco flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-San Francisco flights.
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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. 8% potential increase in price ($30 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 29, 2025.

This Gotogate deal was found by Cheapflights users on 9/28. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/236:24 pmMDW - SFO
1 stop21h 58mFrontier
Thu 10/304:06 pmSFO - MDW
1 stop23h 09mFrontier
Deal found 9/28$217
This Frontier deal was found by Cheapflights users on 9/27. 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.
Mon 10/205:10 amMDW - SFO
1 stop12h 50mFrontier
Mon 10/2710:23 pmSFO - MDW
1 stop11h 15mFrontier
Deal found 9/27$219
This Kiwi.com deal was found by Cheapflights users on 9/27. 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 11/141:37 pmMDW - SFO
1 stop9h 34mFrontier
Wed 11/197:30 amSFO - MDW
2 stops31h 00mFrontier
Deal found 9/27$226
This Frontier deal was found by Cheapflights users on 9/29. 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 11/78:55 amMDW - SFO
2 stops17h 16mFrontier
Sun 11/98:55 pmSFO - MDW
2 stops18h 20mFrontier
Deal found 9/29$230
This Frontier deal was found by Cheapflights users on 9/29. 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 10/245:10 amMDW - SFO
1 stop12h 50mFrontier
Sun 10/268:21 pmSFO - MDW
1 stop12h 55mFrontier
Deal found 9/29$232
This Kiwi.com deal was found by Cheapflights users on 9/26. 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 10/175:10 amMDW - SFO
1 stop12h 50mFrontier
Sun 10/269:08 amSFO - MDW
2 stops13h 28mFrontier
Deal found 9/26$233
This Frontier deal was found by Cheapflights users on 9/29. 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.
Mon 10/205:10 amMDW - SFO
1 stop12h 50mFrontier
Thu 10/233:25 pmSFO - MDW
1 stop7h 11mFrontier
Deal found 9/29$236
This Booking.com deal was found by Cheapflights users on 9/29. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/275:10 amMDW - SFO
1 stop12h 50mFrontier
Thu 10/3012:43 pmSFO - MDW
1 stop20h 47mFrontier
Deal found 9/29$237
This Booking.com deal was found by Cheapflights users on 9/27. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/256:15 amMDW - SFO
1 stop17h 08mFrontier
Sat 11/110:23 pmSFO - MDW
1 stop19h 16mFrontier
Deal found 9/27$239
This Gotogate deal was found by Cheapflights users on 9/29. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1312:30 pmMDW - SFO
1 stop28h 10mFrontier
Thu 11/202:54 pmSFO - MDW
1 stop25h 18mFrontier
Deal found 9/29$241
This Frontier deal was found by Cheapflights users on 9/28. 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 11/91:37 pmMDW - SFO
1 stop9h 34mFrontier
Mon 11/1710:23 pmSFO - MDW
1 stop11h 15mFrontier
Deal found 9/28$242
This Southwest deal was found by Cheapflights users on 9/29. 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 10/222:45 pmMDW - SFO
Nonstop4h 30mSouthwest
Wed 10/291:05 pmSFO - MDW
1 stop8h 30mSouthwest
Deal found 9/29$243

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 September 29, 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 Francisco

MDW - SFO

MDWSFO

Chicago Midway

Wed 12/3

12:05 pm-5:25 pm

1 stop7h 20m

San Francisco

Tue 12/9

6:10 am-12:15 pm

Nonstop4h 05m

$253

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Tue 11/11

10:47 am-6:14 pm

1 stop9h 27m

San Francisco

Wed 11/12

7:15 am-4:39 pm

1 stop7h 24m

$257

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Wed 11/19

5:34 pm-12:13 am

1 stop8h 39m

San Francisco

Wed 12/3

10:45 pm-8:54 am

1 stop8h 09m

$257

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Wed 11/12

6:00 am-12:30 pm

1 stop8h 30m

San Francisco

Wed 11/19

7:15 am-4:39 pm

1 stop7h 24m

$257

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Wed 10/22

1:08 pm-5:51 pm

1 stop6h 43m

San Francisco

Tue 10/28

12:35 am-8:55 am

1 stop6h 20m

$257

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Tue 10/21

5:30 pm-11:05 pm

2 stops7h 35m

San Francisco

Tue 10/28

6:30 am-12:35 pm

Nonstop4h 05m

$258

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Thu 10/23

12:55 pm-3:25 pm

Nonstop4h 30m

San Francisco

Wed 10/29

1:05 pm-11:35 pm

1 stop8h 30m

$266

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Sat 10/25

8:15 am-10:50 am

Nonstop4h 35m

San Francisco

Tue 10/28

6:30 am-12:35 pm

Nonstop4h 05m

$271

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Thu 10/23

8:00 am-12:25 pm

1 stop6h 25m

Oakland

Wed 10/29

4:10 pm-12:25 am

1 stop6h 15m

$271

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Thu 10/23

12:48 pm-6:56 pm

1 stop8h 08m

San Francisco

Tue 10/28

12:35 am-8:55 am

1 stop6h 20m

$273

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/26

Showing 1-10 of 54 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 $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 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 September 29, 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 September 29, 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
4,245 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

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
4,245 reviews
Southwest
8.0
Very good
4,245 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

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
8,924 reviews
Southwest
8.0
Very good
4,245 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

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
3,157 reviews
Southwest
8.0
Very good
4,245 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

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.

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

    There are many flights that can get you from Chicago Midway Airport to San Francisco Bay Area in 7h 20m. Fly via Southwest or Delta to get the fastest option. Airlines will cover a distance of 1849 mi. This flight may include one or multiple stops.

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

    Most travelers choose Chicago Midway - San Francisco, Chicago Midway - San Jose or Chicago Midway - Oakland 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 $406, our data indicates the cheapest price to be $119. The most popular route (Chicago Midway - San Francisco), is priced around $176.

  • 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 $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

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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 September 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$150Average$324FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$217Average$418FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$227Average$428FlexibilityNo cancel feeOn-time63%

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