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$119+ 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 2/18. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SFO
Jan 30 — Feb 61
Fri 1/30
Fri 2/6
1 adult, Economy
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Cheap 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 December 31, 2025.

This Delta deal was found by Cheapflights users on 12/30. 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.
Wed 12/319:29 amMDW - SFO
1 stop7h 10mDelta
Wed 1/710:54 pmSFO - MDW
1 stop7h 58mDelta
Deal found 12/30$688
This Delta deal was found by Cheapflights users on 12/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/309:29 amMDW - SFO
1 stop7h 10mDelta
Fri 1/96:00 amSFO - MDW
1 stop8h 29mDelta
Deal found 12/29$722
This Delta deal was found by Cheapflights users on 12/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/295:05 pmMDW - SFO
1 stop8h 52mDelta
Wed 1/72:25 pmSFO - MDW
2 stops18h 02mDelta
Deal found 12/29$811
This Delta deal was found by Cheapflights users on 12/30. 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.
Wed 12/319:29 amMDW - SFO
1 stop7h 10mDelta
Sun 1/410:45 pmSFO - MDW
1 stop8h 07mDelta
Deal found 12/30$843
This Delta deal was found by Cheapflights users on 12/30. 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.
Wed 12/316:00 amMDW - SFO
1 stop8h 51mDelta
Thu 1/110:45 pmSFO - MDW
1 stop8h 04mDelta
Deal found 12/30$853
This Delta deal was found by Cheapflights users on 12/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/305:59 pmMDW - SFO
1 stop8h 00mDelta
Mon 1/510:55 pmSFO - MDW
2 stops15h 34mDelta
Deal found 12/29$856
This Southwest deal was found by Cheapflights users on 12/29. 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.
Tue 12/301:25 pmMDW - SFO
Nonstop4h 40mSouthwest
Mon 1/56:10 amSFO - MDW
Nonstop4h 05mSouthwest
Deal found 12/29$868
This Southwest deal was found by Cheapflights users on 12/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/314:05 pmMDW - OAK
Nonstop4h 35mSouthwest
Mon 1/55:25 amOAK - MDW
Nonstop4h 05mSouthwest
Deal found 12/28$868
This Delta deal was found by Cheapflights users on 12/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/305:59 pmMDW - SFO
1 stop8h 00mDelta
Fri 1/210:30 pmSFO - MDW
1 stop8h 35mDelta
Deal found 12/29$877
This Southwest deal was found by Cheapflights users on 12/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/307:05 pmMDW - OAK
1 stop6h 40mSouthwest
Sun 1/43:45 pmOAK - MDW
1 stop6h 25mSouthwest
Deal found 12/28$892
This Delta deal was found by Cheapflights users on 12/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/305:59 pmMDW - SFO
1 stop8h 00mDelta
Thu 1/84:05 pmSFO - MDW
2 stops16h 22mDelta
Deal found 12/29$896
This Southwest deal was found by Cheapflights users on 12/30. 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 12/315:15 pmMDW - SJC
1 stop6h 35mSouthwest
Tue 1/68:40 amSJC - MDW
1 stop5h 55mSouthwest
Deal found 12/30$987

Find 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 December 31, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$242
(Southwest)

One-way from

$119
(Southwest)

Popular in

December

Cheapest in

July

Average price

$449
Provider with most accurate pricing for Chicago (CHI)-San Francisco flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-San Francisco flights.
Search Deals
From Chicago Midway to San Francisco Bay Area
Search Deals
One-way flight from Chicago Midway to San Francisco Bay Area
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($59 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 31, 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

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Sat 1/17

2:35 pm-7:20 pm

1 stop6h 45m

Oakland

Wed 1/21

11:10 am-5:15 pm

Nonstop4h 05m

$242

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Thu 3/5

1:29 pm-6:36 pm

1 stop7h 07m

San Francisco

Tue 3/10

12:06 pm-10:31 pm

1 stop8h 25m

$249

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Sat 3/21

9:40 pm-12:20 am

Nonstop4h 40m

San Francisco

Wed 3/25

11:00 am-8:25 pm

1 stop7h 25m

$255

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Tue 2/3

1:26 pm-6:38 pm

1 stop7h 12m

San Francisco

Fri 2/13

12:40 am-11:03 am

1 stop8h 23m

$257

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Sun 1/18

6:14 pm-11:25 pm

1 stop7h 11m

San Francisco

Tue 1/27

8:00 am-5:29 pm

1 stop7h 29m

$257

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Tue 2/3

11:10 am-2:05 pm

Nonstop4h 55m

Oakland

Tue 2/17

2:45 pm-12:25 am

1 stop7h 40m

$257

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Sat 1/24

1:26 pm-6:38 pm

1 stop7h 12m

San Francisco

Wed 2/4

11:40 am-10:22 pm

1 stop8h 42m

$257

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Sat 1/24

1:26 pm-6:38 pm

1 stop7h 12m

San Francisco

Sat 1/31

6:10 am-4:16 pm

1 stop8h 06m

$257

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Tue 3/10

9:00 pm-11:40 pm

Nonstop4h 40m

Oakland

Fri 3/13

11:55 pm-5:55 am

Nonstop4h 00m

$265

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Sat 1/17

11:21 am-9:38 pm

2 stops12h 17m

Oakland

Wed 1/21

5:55 am-6:36 pm

2 stops10h 41m

$266

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/30

Showing 1-10 of 58 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, October is the cheapest month in which you can book a flight from Chicago Midway Airport to San Francisco Bay Area (average of $145). Flying from Chicago Midway Airport to San Francisco Bay Area in December is currently the most expensive (average of $344). 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 December 31, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 18% on flights from Chicago Midway Airport to San Francisco Bay Area by exploring options for tickets in the afternoon.

What is the cheapest day to fly from Chicago Midway Airport to San Francisco Bay Area?

Use this chart to determine the cheapest time to fly round-trip from Midway to San Francisco Bay Area. Price data was last updated on December 27, 2025.

Travelers seeking maximum savings on their Chicago Midway Airport to San Francisco Bay Area flight should consider departing on Tuesday afternoons when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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 December 31, 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
4,252 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Food

7.0

Boarding

8.1

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
4,252 reviews
Southwest
8.0
Very good
4,252 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Food

7.0

Boarding

8.1

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
9,125 reviews
Southwest
8.0
Very good
4,252 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Food

7.0

Boarding

8.1

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
3,068 reviews
Southwest
8.0
Very good
4,252 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Food

7.0

Boarding

8.1

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 6h 45m. Fly via Southwest or Delta to get the fastest option. Airlines will cover a distance of 1839 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Chicago Midway Airport to San Francisco Bay Area one-way?

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $96. Southwest flights start at $98 while deals on Delta start at $128 one-way.

  • 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 $333, our data indicates the cheapest price to be $139. The most popular route (Chicago Midway - San Francisco), is priced around $195.

  • 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, October is the cheapest month in which you can book a flight from Chicago Midway Airport to San Francisco Bay Area (average of $145). Flying from Chicago Midway Airport to San Francisco Bay Area in December is currently the most expensive (average of $344). 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 December 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$90Average$217FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$217Average$418FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$217Average$447FlexibilityNo cancel feeOn-time63%

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