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$100+ 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 2/27. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SFO
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
1 adult, Economy
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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 November 13, 2025.

This Southwest deal was found by Cheapflights users on 11/10. 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.
Fri 12/59:40 amMDW - SFO
1 stop7h 00mSouthwest
Mon 12/86:10 amSFO - MDW
Nonstop4h 05mSouthwest
Deal found 11/10$249
This Kiwi.com deal was found by Cheapflights users on 11/11. 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.
Sun 12/2110:50 pmMDW - SFO
2 stops24h 59mFrontier
Sat 12/2711:32 amSFO - MDW
1 stop24h 27mFrontier
Deal found 11/11$251
This Southwest deal was found by Cheapflights users on 11/11. 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 12/68:15 amMDW - SFO
Nonstop4h 45mSouthwest
Sat 12/135:30 amSFO - MDW
2 stops9h 00mSouthwest
Deal found 11/11$254
This Kiwi.com deal was found by Cheapflights users on 11/11. 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.
Mon 11/247:10 pmMDW - SFO
2 stops38h 58mFrontier
Fri 11/286:32 amSFO - MDW
1 stop9h 40mFrontier
Deal found 11/11$257
This Delta deal was found by Cheapflights users on 11/10. 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.
Sat 12/69:29 amMDW - SFO
1 stop6h 54mDelta
Thu 1/812:47 amSFO - MDW
1 stop6h 21mDelta
Deal found 11/10$259
This Southwest deal was found by Cheapflights users on 11/10. 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.
Fri 12/52:35 pmMDW - OAK
1 stop7h 15mSouthwest
Tue 1/62:50 pmOAK - MDW
1 stop5h 50mSouthwest
Deal found 11/10$259
This Frontier deal was found by Cheapflights users on 11/11. 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.
Thu 12/186:12 amMDW - SFO
1 stop9h 01mFrontier
Sun 1/116:15 amSFO - MDW
1 stop11h 47mFrontier
Deal found 11/11$260
This Frontier deal was found by Cheapflights users on 11/12. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/296:12 amMDW - SFO
1 stop9h 01mFrontier
Fri 1/96:15 amSFO - MDW
1 stop11h 47mFrontier
Deal found 11/12$261
This Frontier deal was found by Cheapflights users on 11/12. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/216:00 amMDW - SFO
1 stop9h 13mFrontier
Sun 12/2811:20 pmSFO - MDW
1 stop12h 01mFrontier
Deal found 11/12$263
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/47:23 pmMDW - SFO
1 stop19h 55mFrontier
Mon 12/86:30 amSFO - MDW
2 stops13h 42mFrontier
Deal found 11/12$264
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/117:23 pmMDW - SFO
1 stop19h 55mFrontier
Thu 12/186:00 amSFO - MDW
2 stops29h 59mFrontier
Deal found 11/12$265
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/266:05 amMDW - SFO
1 stop15h 18mFrontier
Mon 12/16:32 pmSFO - MDW
2 stops12h 45mFrontier
Deal found 11/12$266

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 November 13, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$249
(Southwest)

One-way from

$100
(Kiwi.com)

Popular in

November

Cheapest in

July

Average price

$421
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 ($56 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 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 November 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

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Fri 12/5

2:35 pm-7:50 pm

1 stop7h 15m

Oakland

Tue 1/6

2:50 pm-10:40 pm

1 stop5h 50m

$259

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Sat 12/6

9:29 am-4:10 pm

2 stops8h 41m

Oakland

Wed 1/7

5:55 am-6:32 pm

2 stops10h 37m

$269

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Sat 12/6

2:45 pm-8:20 pm

1 stop7h 35m

San Francisco

Sat 12/13

10:10 am-4:10 pm

Nonstop4h 00m

$269

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Sat 12/6

2:05 pm-4:45 pm

Nonstop4h 40m

Oakland

Sun 12/7

5:25 am-11:30 am

Nonstop4h 05m

$269

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Sat 12/6

9:29 am-2:23 pm

1 stop6h 54m

San Francisco

Sat 12/13

6:00 am-3:44 pm

1 stop7h 44m

$279

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Wed 12/17

1:50 pm-8:28 pm

1 stop8h 38m

San Francisco

Wed 1/7

11:46 am-10:09 pm

1 stop8h 23m

$279

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Fri 12/5

4:05 pm-6:40 pm

Nonstop4h 35m

Oakland

Sat 12/6

5:05 am-1:20 pm

1 stop6h 15m

$279

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Mon 12/8

4:15 pm-8:45 pm

1 stop6h 30m

Oakland

Tue 12/9

11:00 am-5:05 pm

Nonstop4h 05m

$279

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Fri 1/9

5:35 pm-10:15 pm

1 stop6h 40m

Oakland

Sat 1/10

5:55 am-12:00 pm

Nonstop4h 05m

$279

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Mon 12/8

1:14 pm-10:31 pm

2 stops11h 17m

San Francisco

Sun 12/14

12:30 am-9:19 am

1 stop6h 49m

$286

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/10

Showing 1-10 of 55 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 November is currently the most expensive (average of $307). 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 November 13, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 17% 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 16, 2024.

Travelers seeking maximum savings on their Chicago Midway Airport to San Francisco Bay Area flight should consider departing on Thursday evenings 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.

Weekly flight availability from Chicago Midway Airport to San Francisco Bay Area

Explore weekly flight availability from Midway to San Francisco Bay Area. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated November 13, 2025.

The most flights from MDW to zzXIH are scheduled on a Monday (2 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (1 on average).

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 November 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
4,236 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

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
4,236 reviews
Southwest
8.0
Very good
4,236 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

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
9,015 reviews
Southwest
8.0
Very good
4,236 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

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
3,114 reviews
Southwest
8.0
Very good
4,236 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

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 15m. 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 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 $366, our data indicates the cheapest price to be $134. The most popular route (Chicago Midway - San Francisco), is priced around $146.

  • 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 November is currently the most expensive (average of $307). 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 November 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$90Average$313FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$217Average$418FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$227Average$453FlexibilityNo cancel feeOn-time63%

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