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Midway

$100+ Cheap flights from San Francisco (SFO) 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 11/16. Fares are subject to change and may not be available on all flights or dates of travel.
SFO — MDW
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheapflights Tip: The best prices from San Francisco to Chicago Midway are usually found in January or November, booked 40 days in advance, depart on a Thursday or Wednesday and return on a Thursday

Cheap flight deals from San Francisco to Midway

Discover tips and strategies to find the most affordable flight options for your journey from San Francisco (SFO) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 17, 2025.

Round-trip from

$206
(Kiwi.com)

One-way from

$100
(Booking.com)

Popular in

July

Cheapest in

January

Average price

$376

Good round-trip deal

$317 or less

Good one-way deal

$209 or less
From San Francisco to Chicago Midway
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One-way flight from San Francisco to Chicago Midway
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Highest demand for flights based on searches. 7% potential increase in price ($27 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from San Francisco to Chicago Midway.
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Price to beat on a one-way flight from San Francisco to Chicago Midway.
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Find flight deals from San Francisco to Midway

Cheapest flights from San Francisco to Midway
Explore the most affordable flight options available from San Francisco to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/319:55 pmSFO - MDW
1 stop15h 02mFrontier
Fri 11/71:37 pmMDW - SFO
1 stop9h 34mFrontier
Deal found 9/16$206
This CheapOair deal was found by Cheapflights users on 9/15. 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 11/136:33 pmSFO - MDW
2 stops14h 57mFrontier
Sun 11/1612:30 pmMDW - SFO
1 stop13h 44mFrontier
Deal found 9/15$207
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 11/148:55 pmSFO - MDW
1 stop15h 02mFrontier
Mon 11/171:37 pmMDW - SFO
1 stop9h 34mFrontier
Deal found 9/15$208
This Priceline deal was found by Cheapflights users on 9/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/2811:57 pmSFO - MDW
1 stop11h 14mFrontier
Mon 10/206:24 pmMDW - SFO
1 stop7h 50mFrontier
Deal found 9/15$210
This CheapOair deal was found by Cheapflights users on 9/15. 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.
Mon 10/1310:17 pmSFO - MDW
2 stops23h 03mFrontier
Mon 10/205:10 amMDW - SFO
1 stop12h 50mFrontier
Deal found 9/15$211
This CheapOair deal was found by Cheapflights users on 9/16. 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 10/211:57 pmSFO - MDW
1 stop18h 55mFrontier
Mon 10/206:24 pmMDW - SFO
1 stop7h 50mFrontier
Deal found 9/16$212
This Mytrip deal was found by Cheapflights users on 9/14. 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.
Fri 10/311:57 pmSFO - MDW
1 stop8h 31mFrontier
Fri 10/105:10 amMDW - SFO
1 stop12h 50mFrontier
Deal found 9/14$213
This CheapOair deal was found by Cheapflights users on 9/15. 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.
Fri 10/1710:43 pmSFO - MDW
2 stops22h 37mFrontier
Mon 10/205:10 amMDW - SFO
1 stop12h 50mFrontier
Deal found 9/15$214
This Priceline deal was found by Cheapflights users on 9/16. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/66:29 amSFO - MDW
1 stop7h 24mFrontier
Thu 10/96:24 pmMDW - SFO
1 stop7h 50mFrontier
Deal found 9/16$215
This CheapOair deal was found by Cheapflights users on 9/14. 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.
Mon 10/1310:23 pmSFO - MDW
1 stop13h 15mFrontier
Sat 10/186:15 amMDW - SFO
1 stop17h 08mFrontier
Deal found 9/14$216
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/193:17 pmSFO - MDW
2 stops31h 07mFrontier
Thu 10/236:24 pmMDW - SFO
1 stop7h 50mFrontier
Deal found 9/16$217
This CheapOair deal was found by Cheapflights users on 9/15. 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 10/166:34 amSFO - MDW
1 stop16h 02mFrontier
Mon 10/206:24 pmMDW - SFO
1 stop7h 50mFrontier
Deal found 9/15$218

Cheapflights Fare Finder

 
Customize your flight search to find flights from San Francisco 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 September 17, 2025.
Use the filters below to find and compare flights from San Francisco to Chicago Midway Airport that are best for you.

Fly from

San Francisco

Fly to

Midway

Route

Depart

Return

Price

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Sat 11/1

10:57 pm-9:40 am

1 stop8h 43m

Chicago Midway

Wed 11/5

10:40 am-5:22 pm

1 stop8h 42m

$297

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Tue 10/14

5:30 am-3:10 pm

1 stop7h 40m

Chicago Midway

Wed 10/15

5:50 am-1:20 pm

1 stop9h 30m

$297

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Tue 11/4

12:35 am-8:55 am

1 stop6h 20m

Chicago Midway

Mon 11/10

7:02 pm-12:12 am

1 stop7h 10m

$297

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Fri 10/31

12:35 am-10:30 am

1 stop7h 55m

Chicago Midway

Sat 11/1

3:00 pm-8:40 pm

1 stop7h 40m

$297

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Mon 10/13

6:00 am-12:05 pm

Nonstop4h 05m

Chicago Midway

Tue 10/21

5:30 pm-11:05 pm

2 stops7h 35m

$302

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Thu 11/27

6:15 am-12:20 pm

Nonstop4h 05m

Chicago Midway

Sat 12/6

2:45 pm-8:20 pm

1 stop7h 35m

$307

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Sat 11/15

10:10 am-4:10 pm

Nonstop4h 00m

Chicago Midway

Sat 11/22

7:00 pm-12:30 am

1 stop7h 30m

$307

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Fri 11/7

7:45 am-6:30 pm

2 stops8h 45m

Chicago Midway

Tue 11/11

5:25 am-11:30 am

1 stop8h 05m

$325

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Fri 10/24

3:10 pm-12:35 am

1 stop7h 25m

Chicago Midway

Tue 10/28

2:45 pm-5:15 pm

Nonstop4h 30m

$342

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Wed 10/15

6:30 am-12:35 pm

Nonstop4h 05m

Chicago Midway

Sat 10/18

1:45 pm-8:45 pm

1 stop9h 00m

$342

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 21 results
1
2
3

Best time to book a flight from San Francisco to Midway

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

How far ahead should I book a flight from San Francisco to Chicago Midway Airport?

Use this chart to determine the optimal time to book a round-trip flight from San Francisco to Midway. Price data was last updated on September 12, 2025.

The best time to book flights from San Francisco to Chicago Midway Airport is 40 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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

Currently, April is the cheapest month in which you can book a flight from San Francisco to Chicago Midway Airport (average of $160). Flying from San Francisco to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 SFO to MDW?

Find hourly flight availability from San Francisco 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 September 17, 2025.

It’s typically best to fly out from San Francisco to Chicago Midway Airport in the evening. Doing so could potentially save you 47% on the flight price compared to flying at noon, which is usually more expensive.

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

Use this chart to determine the cheapest time to fly round-trip from San Francisco to Midway. Price data was last updated on September 14, 2025.

Travelers seeking maximum savings on their San Francisco to Chicago Midway Airport flight should consider departing on Friday 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 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 September 17, 2025.
Read through reviews of airlines operating flights from San Francisco to Chicago Midway Airport, such as Southwest, Delta, and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

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

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

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.
Delta
8.0
Very good
7,961 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

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
8,926 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

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.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

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
3,173 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

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 San Francisco to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from San Francisco to Chicago Midway?

    San Francisco (SFO), located 11.8 mi from the city center, is the airport you fly out of when you book flights from San Francisco to Chicago Midway. 6 airlines have flights from San Francisco to Chicago Midway on a regular basis. Booking flights from San Francisco to Chicago Midway should not be difficult; the airport handles an average of 1 outbound flight to Chicago Midway per day.

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

    Delta and Southwest can get you from San Francisco to Chicago Midway Airport in just under 7h 40m. Your travel time can differ by up to 1h 03m. The distance from San Francisco to Chicago Midway Airport is about 1849 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from San Francisco to Chicago Midway Airport round-trip?

    Cheapflights users have booked flights from San Francisco to Chicago Midway Airport round-trip from $133. Other airlines that can offer you cheap pricing are Frontier, from $140, and American Airlines, from $197. These flights start at 60% lower than the current average price 3 months from now.

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

    On average you can expect to pay $344 for a flight from San Francisco to Chicago Midway Airport. The cheapest flight overall is $98 while the most popular route, (San Francisco - Chicago Midway) is currently priced at $203.

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

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

  • How can I find direct flights from San Francisco 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 to Midway.

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

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

    Currently, April is the cheapest month in which you can book a flight from San Francisco to Chicago Midway Airport (average of $160). Flying from San Francisco to Chicago Midway Airport in November is currently the most expensive (average of $249). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for San Francisco to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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Top 6 airlines flying from San Francisco to Midway

Discover the top 6 airlines that operate flights from San Francisco 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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$133Average$307FlexibilityNo cancel feeOn-time69%
FrontierCheapest$140Average$239FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$197Average$332FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$197Average$280FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$216Average$397FlexibilityNo cancel feeOn-time63%
DeltaCheapest$256Average$357FlexibilityNo cancel feeOn-timeN/A

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