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$95+ 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 8/23. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SFO
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$204
(Southwest)

One-way from

$95
(Southwest)

Popular in

December

Cheapest in

September

Average price

$326
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 ($28 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 June 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 June 12, 2025.

This Southwest deal was found by Cheapflights users on 6/11. 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 9/1110:50 amMDW - OAK
1 stop6h 15mSouthwest
Mon 9/158:30 pmOAK - MDW
1 stop6h 40mSouthwest
Deal found 6/11$199
This Southwest deal was found by Cheapflights users on 6/11. 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 9/69:45 amMDW - SFO
2 stops10h 35mSouthwest
Sat 9/136:20 pmSFO - MDW
1 stop8h 50mSouthwest
Deal found 6/11$204
This FlightHub deal was found by Cheapflights users on 6/10. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/226:31 pmMDW - SFO
1 stop7h 48mFrontier
Mon 8/2510:29 pmSFO - MDW
1 stop8h 33mFrontier
Deal found 6/10$252
This Delta deal was found by Cheapflights users on 6/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/14:26 pmMDW - SFO
1 stop8h 22mDelta
Mon 8/412:50 amSFO - MDW
1 stop5h 55mDelta
Deal found 6/10$257
This Delta deal was found by Cheapflights users on 6/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/19:24 amMDW - OAK
2 stops8h 52mDelta
Tue 7/84:55 pmOAK - MDW
2 stops13h 49mDelta
Deal found 6/10$308
This Frontier deal was found by Cheapflights users on 6/11. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/46:25 amMDW - SJC
1 stop8h 58mFrontier
Thu 7/1012:18 pmSJC - MDW
1 stop6h 36mFrontier
Deal found 6/11$310
This Delta deal was found by Cheapflights users on 6/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2012:43 pmMDW - SJC
1 stop9h 04mDelta
Tue 8/2610:56 pmSJC - MDW
1 stop7h 39mDelta
Deal found 6/10$319
This Southwest deal was found by Cheapflights users on 6/12. 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 8/77:55 pmMDW - SJC
Nonstop4h 30mSouthwest
Wed 8/136:35 amSJC - MDW
Nonstop4h 10mSouthwest
Deal found 6/12$351
This Trip.com deal was found by Cheapflights users on 6/10. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/239:12 pmMDW - SJC
2 stops28h 22mMultiple Airlines
Thu 6/263:26 pmSJC - MDW
2 stops21h 30mMultiple Airlines
Deal found 6/10$400
This Mytrip deal was found by Cheapflights users on 6/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/1011:37 amMDW - OAK
3 stops22h 51mMultiple Airlines
Sun 7/136:00 amOAK - MDW
2 stops25h 41mMultiple Airlines
Deal found 6/10$491

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 June 12, 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

Sat 9/6

9:45 am-6:20 pm

2 stops10h 35m

San Francisco

Sat 9/13

6:20 pm-5:10 am

1 stop8h 50m

$204

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Thu 7/3

7:20 am-9:50 am

Nonstop4h 30m

Oakland

Mon 7/7

9:15 pm-5:00 am

1 stop5h 45m

$227

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Fri 8/22

6:31 pm-12:19 am

1 stop7h 48m

San Francisco

Mon 8/25

10:29 pm-9:02 am

1 stop8h 33m

$252

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Tue 7/1

9:24 am-2:34 pm

1 stop7h 10m

San Francisco

Fri 7/4

12:49 am-8:44 am

1 stop5h 55m

$257

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Tue 7/1

9:24 am-4:16 pm

2 stops8h 52m

Oakland

Tue 7/8

4:55 pm-8:44 am

2 stops13h 49m

$308

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Fri 7/4

6:25 am-1:23 pm

1 stop8h 58m

San Jose

Thu 7/10

12:18 pm-8:54 pm

1 stop6h 36m

$310

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Wed 8/20

12:43 pm-7:47 pm

1 stop9h 04m

San Jose

Tue 8/26

10:56 pm-8:35 am

1 stop7h 39m

$319

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Thu 8/7

7:55 pm-10:25 pm

Nonstop4h 30m

San Jose

Wed 8/13

6:35 am-12:45 pm

Nonstop4h 10m

$351

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Mon 6/23

9:12 pm-11:34 pm

2 stops28h 22m

San Jose

Thu 6/26

3:26 pm-2:56 pm

2 stops21h 30m

$400

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Thu 7/10

11:37 am-8:28 am

3 stops22h 51m

Oakland

Sun 7/13

6:00 am-9:41 am

2 stops25h 41m

$491

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Showing 1-10 of 21 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 $364). 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 June 12, 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.

Rainfall in San Francisco Bay Area by month

Plan your trip to San Francisco Bay Area by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in San Francisco Bay Area ranges from 0.0 - 4.4 inches per month. January is typically the wettest month, when rainfall can reach 4.4 in. July is typically the driest time to visit San Francisco Bay Area when rainfall is around 0.0 in.

Temperature in San Francisco Bay Area by month

Plan your trip to San Francisco Bay Area by taking into account the average temperature totals by month.

If weather is an important factor for your trip to San Francisco Bay Area, use this chart to help with planning. For those seeking warmer temperatures, September is the ideal time of year to visit, when temperatures reach an average of 62.6 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 51.8 F).

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 June 12, 2025.
Read reviews from past customers who have flown Southwest, Delta and Frontier from Chicago to San Francisco Bay Area. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Crew

8.6

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Southwest
8.0
Very good
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Crew

8.6

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Delta
8.0
Very good
7,946 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Crew

8.6

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Frontier
6.0
Okay
3,295 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Crew

8.6

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

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

    To fly one-way, consider booking your trip with Southwest, which is currently one of the cheapest options available, starting at $95. Frontier flights start at $126 while deals on Delta start at $129 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 - 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 $373, our data indicates the cheapest price to be $74. The most popular route (Chicago Midway - San Francisco), is priced around $179.

  • 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 $364). 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 4 airlines flying from Midway to San Francisco Bay Area

Discover the top 4 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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$78Average$262FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$179Average$319FlexibilityNo cancel feeOn-time69%
DeltaCheapest$236Average$448FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$247Average$419FlexibilityNo cancel feeOn-time63%

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