$126+ 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 2/19. Fares are subject to change and may not be available on all flights or dates of travel.
SFO — MDW
Jan 25 — Feb 11
1 adult, Economy
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Find cheap flights from San Francisco to Midway with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from San Francisco to Chicago Midway are usually found in January or February, booked 33 days in advance, depart on a Tuesday or Wednesday and return on a Saturday
Cheap flight deals from San Francisco to Midway
Cheapest flights from San Francisco to MidwayExplore 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 December 26, 2025.
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 December 26, 2025.
This Delta deal was found by Cheapflights users on 12/23. 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 12/315:50 amSFO - MDW
1 stop9h 36mDelta
Sat 1/36:00 amMDW - SFO
1 stop8h 51mDelta
Deal found 12/23![Delta logo]()
$392
This Expedia deal was found by Cheapflights users on 12/25. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/306:24 amSFO - MDW
1 stop11h 31mFrontier
Thu 1/16:12 amMDW - SFO
1 stop9h 01mFrontier
Deal found 12/25![Frontier logo]()
$407
This Priceline deal was found by Cheapflights users on 12/25. 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.
Fri 12/2611:20 pmSFO - MDW
1 stop12h 01mFrontier
Thu 1/16:12 amMDW - SFO
1 stop9h 01mFrontier
Deal found 12/25![Frontier logo]()
$452
This Expedia deal was found by Cheapflights users on 12/24. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/2811:20 pmSFO - MDW
1 stop12h 01mFrontier
Tue 12/306:14 amMDW - SFO
1 stop8h 59mFrontier
Deal found 12/24![Frontier logo]()
$462
This CheapOair deal was found by Cheapflights users on 12/24. 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 12/2611:20 pmSFO - MDW
1 stop12h 01mFrontier
Mon 1/56:12 amMDW - SFO
1 stop9h 01mFrontier
Deal found 12/24![Frontier logo]()
$473
This Delta deal was found by Cheapflights users on 12/24. 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 12/3111:30 pmSFO - MDW
1 stop7h 35mDelta
Sun 1/412:45 pmMDW - SFO
1 stop10h 05mDelta
Deal found 12/24![Delta logo]()
$478
This Southwest deal was found by Cheapflights users on 12/23. 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 12/312:35 pmSFO - MDW
1 stop12h 30mSouthwest
Sat 1/311:55 amMDW - SFO
2 stops10h 15mSouthwest
Deal found 12/23![Southwest logo]()
$484
This Frontier deal was found by Cheapflights users on 12/24. 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 12/2811:20 pmSFO - MDW
1 stop12h 01mFrontier
Thu 1/16:12 amMDW - SFO
1 stop9h 01mFrontier
Deal found 12/24![Frontier logo]()
$492
This Priceline deal was found by Cheapflights users on 12/25. 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.
Fri 12/2611:20 pmSFO - MDW
1 stop12h 01mFrontier
Sun 12/286:00 amMDW - SFO
1 stop9h 13mFrontier
Deal found 12/25![Frontier logo]()
$502
Find 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 December 26, 2025.
Most accurate provider | CheapOair 3 stars |
|---|---|
Most trusted provider | CheapOair 3 stars |
Round-trip from | $264 (Southwest) |
One-way from | $126 (Kiwi.com) |
Popular in | July |
Cheapest in | January |
Average price | $415 |
Good round-trip deal | $374 or less |
Good one-way deal | $243 or less |
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 December 26, 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
Thu 1/1
10:45 pm-8:49 am
1 stop8h 04m
Chicago Midway
Wed 1/28
9:50 am-5:49 pm
2 stops9h 59m
$265
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Sat 1/17
5:10 am-6:30 pm
2 stops11h 20m
Chicago Midway
Sat 1/24
7:00 am-1:50 pm
1 stop8h 50m
$267
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Wed 2/18
12:40 am-9:06 am
1 stop6h 26m
Chicago Midway
Mon 2/23
1:49 pm-8:57 pm
1 stop9h 08m
$267
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Wed 3/4
10:45 pm-8:54 am
1 stop8h 09m
Chicago Midway
Sun 3/8
7:20 pm-11:56 pm
1 stop6h 36m
$270
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Thu 3/12
5:10 am-11:10 am
Nonstop4h 00m
Chicago Midway
Sat 3/14
9:40 pm-12:20 am
Nonstop4h 40m
$272
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Wed 2/11
12:30 pm-9:50 pm
1 stop7h 20m
Chicago Midway
Mon 3/30
9:25 pm-12:05 am
Nonstop4h 40m
$277
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Thu 2/19
6:25 am-12:25 pm
Nonstop4h 00m
Chicago Midway
Mon 2/23
8:15 am-11:15 am
Nonstop5h 00m
$283
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Thu 2/19
6:25 am-12:25 pm
Nonstop4h 00m
Chicago Midway
Sun 2/22
7:55 am-10:55 am
Nonstop5h 00m
$283
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Tue 2/3
11:10 am-9:50 pm
2 stops8h 40m
Chicago Midway
Thu 2/5
8:15 am-11:15 am
Nonstop5h 00m
$284
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Thu 3/5
5:10 am-11:10 am
Nonstop4h 00m
Chicago Midway
Wed 3/11
10:05 am-12:45 pm
Nonstop4h 40m
$286
Showing 1-10 of 20 results
Compare providers for flights from San Francisco to Midway
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from San Francisco to Midway in December.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*2 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on San Francisco-Chicago Midway Airport flights, users find the pricing of CheapOair to be most consistent on Cheapflights vs. CheapOair Users can find the same prices on San Francisco-Chicago Midway Airport flight deals on Cheapflights vs. CheapOair >95% of the time. Price accuracy is based on data collected from San Francisco-Chicago Midway Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on San Francisco-Chicago Midway Airport flights, Cheapflights users trust CheapOair the most. CheapOair has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for San Francisco-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
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 December 19, 2025.
The best time to book flights from San Francisco to Chicago Midway Airport is 33 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, January is the cheapest month in which you can book a flight from San Francisco to Chicago Midway Airport (average of $146). Flying from San Francisco 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 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 December 26, 2025.
It’s typically best to fly out from San Francisco to Chicago Midway Airport in the afternoon. Doing so could potentially save you 43% on the flight price compared to flying at noon, which is usually more expensive.
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 December 26, 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.
Overall
8.0
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Overall
8.0
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Overall
8.0
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Overall
8.0
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Overall
8.0
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Overall
8.0
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
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.
Traveling to a place near Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
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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.
Top 5 airlines flying from San Francisco to Midway
Discover the top 5 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 December 26, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$133 | Average$407 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$147 | Average$237 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$197 | Average$332 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$217 | Average$392 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$256 | Average$338 | FlexibilityNo cancel fee | On-timeN/A |