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Midway

$125+ Cheap flights from San Francisco Bay Area to Midway (MDW)

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 12/11. Fares are subject to change and may not be available on all flights or dates of travel.
SFO — MDW
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
1 adult, Economy
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Find flight deals from San Francisco Bay Area to Midway

Cheapest flights from San Francisco Bay Area to Midway
Explore the most affordable flight options available from San Francisco Bay Area to Midway. 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 11/12. 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 12/911:00 amOAK - MDW
Nonstop4h 05mSouthwest
Thu 12/114:05 pmMDW - OAK
Nonstop4h 35mSouthwest
Deal found 11/12$269
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/2612:30 amSFO - MDW
1 stop6h 31mDelta
Sat 12/66:00 amMDW - SFO
1 stop8h 25mDelta
Deal found 11/11$288
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.
Wed 12/36:10 amSFO - MDW
Nonstop4h 05mSouthwest
Sat 12/65:55 amMDW - SFO
2 stops9h 45mSouthwest
Deal found 11/11$289
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/105:55 amOAK - MDW
2 stops10h 05mDelta
Sat 12/139:29 amMDW - OAK
2 stops8h 41mDelta
Deal found 11/12$289
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 12/610:10 amSFO - MDW
Nonstop4h 00mSouthwest
Wed 12/108:15 amMDW - SFO
Nonstop4h 45mSouthwest
Deal found 11/11$292
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/610:45 pmSFO - MDW
1 stop8h 09mDelta
Wed 12/101:50 pmMDW - SFO
1 stop8h 38mDelta
Deal found 11/11$294
This Kiwi.com deal was found by Cheapflights users on 11/13. 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 12/2611:20 pmSFO - MDW
1 stop12h 01mMultiple Airlines
Mon 1/56:12 amMDW - SFO
2 stops16h 18mMultiple Airlines
Deal found 11/13$295
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.
Fri 11/216:00 amSFO - MDW
2 stops15h 29mFrontier
Sun 11/235:30 amMDW - SFO
1 stop10h 47mFrontier
Deal found 11/12$296
This CheapOair deal was found by Cheapflights users on 11/13. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/272:54 pmSFO - MDW
1 stop25h 18mFrontier
Thu 12/46:15 amMDW - SFO
1 stop9h 03mFrontier
Deal found 11/13$297
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 12/67:45 amOAK - MDW
1 stop7h 05mSouthwest
Tue 12/94:05 pmMDW - OAK
Nonstop4h 35mSouthwest
Deal found 11/11$297
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/233:12 pmSFO - MDW
1 stop7h 01mFrontier
Wed 11/266:05 amMDW - SFO
1 stop15h 18mFrontier
Deal found 11/12$298
This Delta deal was found by Cheapflights users on 11/13. 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.
Sun 12/1412:30 amSFO - MDW
1 stop6h 49mDelta
Mon 12/157:02 pmMDW - SFO
1 stop7h 17mDelta
Deal found 11/13$299

Cheap flight deals from San Francisco Bay Area to Midway

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

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$269
(Southwest)

One-way from

$125
(Kiwi.com)

Popular in

November

Cheapest in

February

Average price

$471
Provider with most accurate pricing for San Francisco-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for San Francisco-Chicago (CHI) flights.
Search Deals
From San Francisco Bay Area to Chicago Midway
Search Deals
One-way flight from San Francisco Bay Area to Chicago Midway
Search Deals
Highest demand for flights based on searches. 18% potential increase in price ($79 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 November 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from San Francisco Bay Area to Midway 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 San Francisco Bay Area to Chicago Midway Airport that are best for you.

Fly from

San Francisco Bay Area

Fly to

Midway

Route

Depart

Return

Price

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Wed 2/4

10:00 pm-9:58 am

1 stop9h 58m

Chicago Midway

Tue 2/17

1:28 pm-6:38 pm

1 stop7h 10m

$289

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Fri 2/6

6:30 am-12:35 pm

Nonstop4h 05m

Chicago Midway

Sun 2/8

8:15 am-2:35 pm

1 stop8h 20m

$289

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Wed 2/4

10:54 pm-8:54 am

1 stop8h 00m

Chicago Midway

Wed 2/18

7:17 pm-11:49 pm

1 stop6h 32m

$289

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Fri 1/30

11:10 am-5:15 pm

Nonstop4h 05m

Chicago Midway

Mon 2/2

8:15 am-2:35 pm

1 stop8h 20m

$289

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Sat 12/13

5:55 am-6:06 pm

2 stops10h 11m

Chicago Midway

Tue 12/16

1:14 pm-12:08 am

2 stops12h 54m

$289

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Wed 4/1

6:05 am-2:50 pm

1 stop6h 45m

Chicago Midway

Wed 4/8

10:00 am-12:35 pm

Nonstop4h 35m

$289

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Wed 12/10

5:55 am-6:00 pm

2 stops10h 05m

Chicago Midway

Sat 12/13

9:29 am-4:10 pm

2 stops8h 41m

$289

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Wed 12/10

5:55 am-6:00 pm

2 stops10h 05m

Chicago Midway

Tue 12/16

1:14 pm-12:08 am

2 stops12h 54m

$289

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Sat 12/6

10:45 pm-8:54 am

1 stop8h 09m

Chicago Midway

Wed 12/10

1:50 pm-8:28 pm

1 stop8h 38m

$294

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Mon 12/8

12:30 am-9:19 am

1 stop6h 49m

Chicago Midway

Thu 12/11

9:59 am-10:31 pm

2 stops14h 32m

$296

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/10

Showing 1-10 of 59 results
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Best time to book a flight from San Francisco Bay Area to Midway

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

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

Currently, January is the cheapest month in which you can book a flight from San Francisco Bay Area to Chicago Midway Airport (average of $147). Flying from San Francisco Bay Area to Chicago Midway Airport in June is currently the most expensive (average of $242). 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 XIH to MDW?

Find hourly flight availability from San Francisco Bay Area to Midway. 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.

It’s optimal to fly from San Francisco Bay Area to Chicago Midway Airport in the afternoon. By choosing this option you can save up to 34% on the cost of your flight, compared to a flight in the evening.

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

Use this chart to determine the cheapest time to fly round-trip from San Francisco Bay Area to Midway. Price data was last updated on November 2, 2025.

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

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated November 13, 2025.
See what other customers who have flown with Southwest, Delta, and United Airlines from San Francisco Bay Area to Chicago Midway Airport have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

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.
Delta
7.9
Good
8,007 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

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
9,017 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

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.
American Airlines
7.2
Good
11,051 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

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
3,109 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

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 San Francisco Bay Area to Midway. 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 San Francisco Bay Area to Chicago Midway Airport?

    Departing from San Francisco Bay Area to Chicago Midway Airport will take you 4h 05m. San Francisco Bay Area and Chicago Midway Airport are separated by a distance of 1839 mi. This flight may include one or multiple stops.

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

    While some choose either San Jose - Chicago Midway or Oakland - Chicago Midway, San Francisco - Chicago Midway is the most popular route from San Francisco Bay Area to Chicago Midway Airport.

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

    Looking for the cheapest flight from San Francisco Bay Area to Chicago Midway Airport? While on average our users pay $372, our data indicates the cheapest price to be $111. The most popular route (San Francisco - Chicago Midway), is priced around $130.

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

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

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

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from San Francisco Bay Area to Midway.

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

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

    Currently, January is the cheapest month in which you can book a flight from San Francisco Bay Area to Chicago Midway Airport (average of $147). Flying from San Francisco Bay Area to Chicago Midway Airport in June is currently the most expensive (average of $242). 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

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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Alternative routes for San Francisco Bay Area to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from San Francisco Bay Area to Midway

Discover the top 5 airlines that operate flights from San Francisco Bay Area to Midway. 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
United AirlinesCheapest$133Average$426FlexibilityNo cancel feeOn-time69%
FrontierCheapest$147Average$249FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$197Average$332FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$219Average$459FlexibilityNo cancel feeOn-time63%
DeltaCheapest$256Average$338FlexibilityNo cancel feeOn-timeN/A

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