$117+ Cheap flights from Midway (MDW) to San Francisco (SFO)
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 4/13. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SFO
Apr 9 — Apr 161
Round-trip
1 adult, Economy
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Cheapest flights from Midway to San FranciscoExplore the most affordable flight options available from Midway to San Francisco. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 10, 2026.
Explore the most affordable flight options available from Midway to San Francisco. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/9. 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 4/206:00 am
MDW
- SFO
1 stop13h 34m
Frontier
Thu 4/239:58 am
SFO
- MDW
2 stops33h 52m
Frontier
Deal found 3/9![Frontier logo]()
$225
This Southwest deal was found by Cheapflights users on 3/8. 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 5/26:10 am
MDW
- SFO
1 stop10h 15m
Southwest
Sat 5/95:40 am
SFO
- MDW
2 stops9h 35m
Southwest
Deal found 3/8![Southwest logo]()
$226
This Kiwi.com deal was found by Cheapflights users on 3/6. 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 5/86:00 am
MDW
- SFO
1 stop12h 54m
Frontier
Sun 5/1010:03 am
SFO
- MDW
2 stops26h 46m
Frontier
Deal found 3/6![Frontier logo]()
$227
This Southwest deal was found by Cheapflights users on 3/8. 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 4/155:30 am
MDW
- SFO
1 stop7h 35m
Southwest
Sat 4/1811:25 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Deal found 3/8![Southwest logo]()
$229
This Southwest deal was found by Cheapflights users on 3/8. 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 4/1810:30 am
MDW
- SFO
2 stops10h 05m
Southwest
Sat 4/255:40 am
SFO
- MDW
2 stops9h 35m
Southwest
Deal found 3/8![Southwest logo]()
$231
This Expedia deal was found by Cheapflights users on 3/5. 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.
Wed 5/278:05 am
MDW
- SFO
1 stop14h 53m
Frontier
Sun 5/3111:59 pm
SFO
- MDW
1 stop16h 37m
Frontier
Deal found 3/5![Frontier logo]()
$232
This Southwest deal was found by Cheapflights users on 3/7. 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 4/185:10 am
MDW
- SFO
1 stop8h 40m
Southwest
Wed 4/2211:25 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Deal found 3/7![Southwest logo]()
$233
This Southwest deal was found by Cheapflights users on 3/9. 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 4/49:40 pm
MDW
- SFO
Nonstop4h 40m
Southwest
Sat 4/1111:25 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Deal found 3/9![Southwest logo]()
$234
This Trip.com deal was found by Cheapflights users on 3/6. 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.
Tue 4/216:10 am
MDW
- SFO
1 stop13h 24m
Frontier
Sat 4/2510:38 pm
SFO
- MDW
1 stop9h 20m
Frontier
Deal found 3/6![Frontier logo]()
$235
This Kiwi.com deal was found by Cheapflights users on 3/8. 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.
Tue 4/146:10 am
MDW
- SFO
1 stop13h 24m
Frontier
Wed 4/227:00 am
SFO
- MDW
2 stops13h 14m
Frontier
Deal found 3/8![Frontier logo]()
$236
This Delta deal was found by Cheapflights users on 3/5. 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 4/41:10 pm
MDW
- SFO
1 stop8h 18m
Delta
Fri 4/1012:10 am
SFO
- MDW
1 stop6h 40m
Delta
Deal found 3/5![Delta logo]()
$237
Best flights from Midway to San FranciscoDiscover carefully curated flight deals from Midway to San Francisco that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 10, 2026.
Discover carefully curated flight deals from Midway to San Francisco that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 10, 2026.
This Southwest deal was found by Cheapflights users on 3/9. 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 4/49:40 pm
MDW
- SFO
Nonstop4h 40m
Southwest
Tue 4/711:25 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Deal found 3/9![Southwest logo]()
$241
This Delta deal was found by Cheapflights users on 3/6. 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.
Thu 4/231:24 pm
MDW
- SFO
1 stop7h 39m
Delta
Mon 4/2711:39 pm
SFO
- MDW
1 stop8h 17m
Delta
Deal found 3/6![Delta logo]()
$312
This Southwest deal was found by Cheapflights users on 3/9. 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 4/185:10 am
MDW
- SFO
1 stop8h 40m
Southwest
Sat 4/2511:25 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Deal found 3/9![Southwest logo]()
$255
This Southwest deal was found by Cheapflights users on 3/6. 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.
Mon 4/209:45 pm
MDW
- SFO
Nonstop4h 35m
Southwest
Mon 4/2711:25 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Deal found 3/6![Southwest logo]()
$267
This Southwest deal was found by Cheapflights users on 3/8. 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.
Sun 4/55:55 am
MDW
- SFO
1 stop6h 35m
Southwest
Tue 4/710:40 pm
SFO
- MDW
1 stop7h 45m
Southwest
Deal found 3/8![Southwest logo]()
$285
This Southwest deal was found by Cheapflights users on 3/5. 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 4/11:20 pm
MDW
- SFO
2 stops10h 45m
Southwest
Mon 4/611:25 pm
SFO
- MDW
Nonstop4h 05m
Southwest
Deal found 3/5![Southwest logo]()
$292
This Southwest deal was found by Cheapflights users on 3/9. 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 5/83:05 pm
MDW
- SFO
2 stops9h 05m
Southwest
Mon 5/116:20 am
SFO
- MDW
2 stops9h 35m
Southwest
Deal found 3/9![Southwest logo]()
$306
This Southwest deal was found by Cheapflights users on 3/8. 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.
Sun 5/39:35 pm
MDW
- SFO
Nonstop4h 35m
Southwest
Thu 5/710:10 am
SFO
- MDW
1 stop9h 25m
Southwest
Deal found 3/8![Southwest logo]()
$306
This Southwest deal was found by Cheapflights users on 3/7. 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.
Mon 6/16:25 pm
MDW
- SFO
1 stop7h 20m
Southwest
Thu 10/16:05 pm
SFO
- MDW
1 stop8h 25m
Southwest
Deal found 3/7![Southwest logo]()
$320
This Southwest deal was found by Cheapflights users on 3/9. 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 4/24:05 pm
MDW
- SFO
2 stops8h 30m
Southwest
Sat 4/1111:25 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Deal found 3/9![Southwest logo]()
$330
Last-minute flights from Midway to San FranciscoDiscover last-minute flight deals from Midway to San Francisco. Data last updated March 10, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to San Francisco. Data last updated March 10, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 3/9. 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 4/49:40 pm
MDW
- SFO
Nonstop4h 40m
Southwest
Sat 4/1111:25 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Deal found 3/9![Southwest logo]()
$234
This Delta deal was found by Cheapflights users on 3/5. 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 4/41:10 pm
MDW
- SFO
1 stop8h 18m
Delta
Fri 4/1012:10 am
SFO
- MDW
1 stop6h 40m
Delta
Deal found 3/5![Delta logo]()
$237
This Southwest deal was found by Cheapflights users on 3/9. 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 4/49:40 pm
MDW
- SFO
Nonstop4h 40m
Southwest
Tue 4/711:25 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Deal found 3/9![Southwest logo]()
$241
This Kiwi.com deal was found by Cheapflights users on 3/8. 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.
Tue 4/146:10 am
MDW
- SFO
1 stop13h 24m
Frontier
Wed 4/227:00 am
SFO
- MDW
2 stops13h 14m
Frontier
Deal found 3/8![Frontier logo]()
$236
This Southwest deal was found by Cheapflights users on 3/8. 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 4/155:30 am
MDW
- SFO
1 stop7h 35m
Southwest
Sat 4/1811:25 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Deal found 3/8![Southwest logo]()
$229
This Southwest deal was found by Cheapflights users on 3/8. 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 4/187:50 am
MDW
- SFO
2 stops9h 35m
Southwest
Sat 4/255:40 am
SFO
- MDW
2 stops9h 35m
Southwest
Deal found 3/8![Southwest logo]()
$231
This Southwest deal was found by Cheapflights users on 3/7. 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 4/185:10 am
MDW
- SFO
1 stop8h 40m
Southwest
Wed 4/2211:25 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Deal found 3/7![Southwest logo]()
$233
This Kiwi.com deal was found by Cheapflights users on 3/9. 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 4/206:00 am
MDW
- SFO
1 stop13h 34m
Frontier
Thu 4/239:58 am
SFO
- MDW
2 stops33h 52m
Frontier
Deal found 3/9![Frontier logo]()
$225
This Southwest deal was found by Cheapflights users on 3/9. 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.
Mon 4/209:45 pm
MDW
- SFO
Nonstop4h 35m
Southwest
Sat 4/2510:10 am
SFO
- MDW
1 stop5h 30m
Southwest
Deal found 3/9![Southwest logo]()
$240
This Delta deal was found by Cheapflights users on 3/8. 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.
Mon 4/207:16 pm
MDW
- SFO
1 stop6h 38m
Delta
Wed 4/2911:59 pm
SFO
- MDW
1 stop6h 47m
Delta
Deal found 3/8![Delta logo]()
$242
This Trip.com deal was found by Cheapflights users on 3/6. 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.
Tue 4/216:10 am
MDW
- SFO
1 stop13h 24m
Frontier
Sat 4/2510:38 pm
SFO
- MDW
1 stop9h 20m
Frontier
Deal found 3/6![Frontier logo]()
$235
One-way flights from Midway to San FranciscoSearch for one-way flight options from Midway to San Francisco. Find affordable one-way fares based on user searches. Data last updated March 10, 2026.
Search for one-way flight options from Midway to San Francisco. Find affordable one-way fares based on user searches. Data last updated March 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/5. 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 4/135:11 pm
MDW
- SFO
2 stops32h 14m
Frontier
Deal found 3/5![Frontier logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 3/5. 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.
Tue 5/192:20 pm
MDW
- SFO
1 stop28h 34m
Frontier
Deal found 3/5![Frontier logo]()
$118
This Southwest deal was found by Cheapflights users on 3/8. 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 3/319:05 pm
MDW
- SFO
Nonstop4h 40m
Southwest
Deal found 3/8![Southwest logo]()
$119
This Super.com deal was found by Cheapflights users on 3/6. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/186:05 am
MDW
- SFO
1 stop15h 09m
Frontier
Deal found 3/6![Frontier logo]()
$120
This Kiwi.com deal was found by Cheapflights users on 3/5. 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 5/156:15 am
MDW
- SFO
2 stops12h 37m
Frontier
Deal found 3/5![Frontier logo]()
$121
This Southwest deal was found by Cheapflights users on 3/9. 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 4/49:40 pm
MDW
- SFO
Nonstop4h 40m
Southwest
Deal found 3/9![Southwest logo]()
$123
This Delta deal was found by Cheapflights users on 3/9. 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.
Mon 4/61:10 pm
MDW
- SFO
1 stop8h 18m
Delta
Deal found 3/9![Delta logo]()
$124
This Frontier deal was found by Cheapflights users on 3/5. 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 3/266:05 am
MDW
- SFO
1 stop15h 09m
Frontier
Deal found 3/5![Frontier logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 3/9. 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.
Tue 5/122:20 pm
MDW
- SFO
2 stops26h 06m
Frontier
Deal found 3/9![Frontier logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 3/6. 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 4/226:15 am
MDW
- SFO
2 stops14h 30m
Frontier
Deal found 3/6![Frontier logo]()
$127
Find flight deals from Midway to San Francisco
Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to San Francisco (SFO). 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 March 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $225 (Kiwi.com) |
One-way from | $117 (Kiwi.com) |
Popular in | February |
Cheapest in | October |
Average price | $418 |
Good round-trip deal | $322 or less |
Good one-way deal | $148 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to San Francisco 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 March 10, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to San Francisco that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Sat 4/4
9:40 pm-12:20 am
Nonstop4h 40m
San Francisco
Tue 4/7
11:25 pm-5:40 am
Nonstop4h 15m
$241
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Sat 4/18
5:10 am-11:50 am
1 stop8h 40m
San Francisco
Sat 4/25
11:25 pm-5:40 am
Nonstop4h 15m
$255
Quickest round-trip
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Mon 4/20
9:45 pm-12:20 am
Nonstop4h 35m
San Francisco
Mon 4/27
11:25 pm-5:40 am
Nonstop4h 15m
$267
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Sun 4/5
5:55 am-10:30 am
1 stop6h 35m
San Francisco
Tue 4/7
10:40 pm-8:25 am
1 stop7h 45m
$285
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Wed 4/1
1:20 pm-10:05 pm
2 stops10h 45m
San Francisco
Mon 4/6
11:25 pm-5:30 am
Nonstop4h 05m
$292
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Fri 5/8
3:05 pm-10:10 pm
2 stops9h 05m
San Francisco
Mon 5/11
6:20 am-5:55 pm
2 stops9h 35m
$306
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Sun 5/3
9:35 pm-12:10 am
Nonstop4h 35m
San Francisco
Thu 5/7
10:10 am-9:35 pm
1 stop9h 25m
$306
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Thu 4/23
1:24 pm-7:03 pm
1 stop7h 39m
San Francisco
Mon 4/27
11:39 pm-9:56 am
1 stop8h 17m
$312
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Mon 6/1
6:25 pm-11:45 pm
1 stop7h 20m
San Francisco
Thu 10/1
6:05 pm-4:30 am
1 stop8h 25m
$320
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Thu 4/2
4:05 pm-10:35 pm
2 stops8h 30m
San Francisco
Sat 4/11
11:25 pm-5:40 am
Nonstop4h 15m
$330
Showing 1-10 of 20 resultsSorted by cheapest first
Compare providers for flights from Midway to San Francisco
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 Midway to San Francisco in March.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago Midway Airport-San Francisco flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-San Francisco flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-San Francisco flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago Midway Airport-San Francisco flights, Cheapflights users trust FlightHub the most. FlightHub 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 Chicago Midway Airport-San Francisco 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 Midway to San Francisco
Have a flexible travel schedule? Discover the best time to fly to San Francisco from Midway with our price prediction graph.
MDW-SFO
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
Prices
Delays
What is the cheapest month to book a flight from Chicago Midway Airport to San Francisco?
Currently, October is the cheapest month in which you can book a flight from Chicago Midway Airport to San Francisco (average of $145). Flying from Chicago Midway Airport to San Francisco in November is currently the most expensive (average of $332). 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 SFO?
Find hourly flight availability from Midway to San Francisco. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated March 10, 2026.
It’s typically best to fly out from Chicago Midway Airport to San Francisco in the evening. Doing so could potentially save you 41% on the flight price compared to flying in the afternoon, which is usually more expensive.
What is the cheapest day to fly from Chicago Midway Airport to San Francisco?
Use this chart to determine the cheapest time to fly round-trip from Midway to San Francisco. Price data was last updated on February 21, 2026.
Travelers seeking maximum savings on their Chicago Midway Airport to San Francisco flight should consider departing on Tuesday afternoons when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
How often are flights from Chicago to San Francisco delayed?
About 25% of weekly flights between Chicago and San Francisco have experienced delays in the past year, with the average delay time being 137 minutes.
What is the most punctual flight time for Chicago to San Francisco flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving at night tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Saturday tends to have the lowest number of delays on this route, whereas Monday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to San Francisco flights?
Over the last year, Southwest have had the lowest number of delays on this route, with just 25% of flights being delayed.
Reviews of airlines servicing San Francisco
Get insights into the airlines that provide service to San Francisco. 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. Reviews last updated March 10, 2026.
Read reviews from past customers who have flown Southwest and United Airlines from Chicago Midway Airport to San Francisco. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentWalter,Aug 2025
OAK - SAN
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentWalter,Aug 2025
OAK - SAN
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentWalter,Aug 2025
OAK - SAN
Related info for your journey
Find useful and relevant information for your journey from Midway to San Francisco. 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 San Francisco?
Book flights to San Francisco if you plan to visit one of these locationsSouth San Francisco
Santa Clara
Santa Cruz
Livermore
Roseville
Watsonville
San Bruno
Sunnyvale
Vacaville
Turlock
San Carlos
San Ramon
Redwood City
Daly City
Rancho Cordova
San Lorenzo
Davis
Hollister
Manteca
Union City
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Midway and San Francisco flights
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Top 2 airlines flying from Midway to San Francisco
Discover the top 2 airlines that operate flights from Midway to San Francisco. 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 March 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$217 | Average$418 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$231 | Average$436 | FlexibilityNo cancel fee | On-time63% |