$139+ 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 9/6. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SFO
Jul 11 — Jul 181
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 June 11, 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 June 11, 2026.
This Southwest deal was found by Cheapflights users on 6/7. 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.
Wed 7/295:30 am
MDW
- SFO
1 stop6h 20m
Southwest
Tue 8/411:05 pm
SFO
- MDW
1 stop9h 50m
Southwest
Deal found 6/7![Southwest logo]()
$294
This Southwest deal was found by Cheapflights users on 6/8. 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.
Thu 9/310:15 am
MDW
- SFO
Nonstop4h 35m
Southwest
Mon 9/75:35 am
SFO
- MDW
Nonstop4h 05m
Southwest
Deal found 6/8![Southwest logo]()
$297
This Trip.com deal was found by Cheapflights users on 6/10. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/306:05 am
MDW
- SFO
1 stop15h 13m
Frontier
Sun 8/210:10 pm
SFO
- MDW
1 stop10h 57m
Frontier
Deal found 6/10![Frontier logo]()
$298
This Southwest deal was found by Cheapflights users on 6/8. 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.
Thu 7/305:20 am
MDW
- SFO
2 stops8h 00m
Southwest
Wed 8/57:25 pm
SFO
- MDW
1 stop7h 05m
Southwest
Deal found 6/8![Southwest logo]()
$299
This Southwest deal was found by Cheapflights users on 6/10. 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 10/236:00 am
MDW
- SFO
1 stop6h 15m
Southwest
Mon 10/265:30 am
SFO
- MDW
Nonstop4h 05m
Southwest
Deal found 6/10![Southwest logo]()
$300
This Frontier deal was found by Cheapflights users on 6/9. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/146:05 am
MDW
- SFO
1 stop15h 13m
Frontier
Tue 7/2110:10 pm
SFO
- MDW
1 stop10h 57m
Frontier
Deal found 6/9![Frontier logo]()
$301
This Expedia deal was found by Cheapflights users on 6/7. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/26:00 am
MDW
- SFO
1 stop15h 26m
Frontier
Thu 7/910:10 pm
SFO
- MDW
1 stop10h 57m
Frontier
Deal found 6/7![Frontier logo]()
$303
This Southwest deal was found by Cheapflights users on 6/8. 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.
Thu 7/95:45 am
MDW
- SFO
1 stop7h 15m
Southwest
Tue 7/1411:40 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Deal found 6/8![Southwest logo]()
$304
This Delta deal was found by Cheapflights users on 6/8. 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.
Wed 12/161:05 pm
MDW
- SFO
1 stop8h 32m
Delta
Fri 12/256:15 am
SFO
- MDW
1 stop8h 35m
Delta
Deal found 6/8![Delta logo]()
$305
This Frontier deal was found by Cheapflights users on 6/11. 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.
Wed 7/294:45 pm
MDW
- SFO
1 stop8h 14m
Frontier
Sun 8/210:10 pm
SFO
- MDW
1 stop10h 57m
Frontier
Deal found 6/11![Frontier logo]()
$306
This Frontier deal was found by Cheapflights users on 6/9. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/276:05 am
MDW
- SFO
1 stop15h 13m
Frontier
Thu 7/3010:10 pm
SFO
- MDW
1 stop10h 57m
Frontier
Deal found 6/9![Frontier logo]()
$307
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 June 11, 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 June 11, 2026.
This Delta deal was found by Cheapflights users on 6/10. 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.
Tue 8/45:10 pm
MDW
- SFO
1 stop8h 48m
Delta
Mon 8/1012:12 am
SFO
- MDW
1 stop6h 27m
Delta
Deal found 6/10![Delta logo]()
$308
This Southwest deal was found by Cheapflights users on 6/10. 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.
Tue 7/146:10 am
MDW
- SFO
1 stop9h 30m
Southwest
Sat 7/183:25 pm
SFO
- MDW
1 stop6h 45m
Southwest
Deal found 6/10![Southwest logo]()
$323
This Delta deal was found by Cheapflights users on 6/9. 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.
Sat 7/49:54 am
MDW
- SFO
1 stop8h 30m
Delta
Mon 7/612:35 am
SFO
- MDW
1 stop6h 02m
Delta
Deal found 6/9![Delta logo]()
$314
This Southwest deal was found by Cheapflights users on 6/6. 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.
Thu 9/175:30 am
MDW
- SFO
1 stop8h 05m
Southwest
Mon 9/215:35 am
SFO
- MDW
Nonstop4h 05m
Southwest
Deal found 6/6![Southwest logo]()
$345
This Delta deal was found by Cheapflights users on 6/10. 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 7/189:54 am
MDW
- SFO
1 stop8h 31m
Delta
Mon 7/2012:35 am
SFO
- MDW
1 stop6h 02m
Delta
Deal found 6/10![Delta logo]()
$314
This Southwest deal was found by Cheapflights users on 6/10. 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.
Thu 7/28:40 am
MDW
- SFO
1 stop7h 45m
Southwest
Sat 7/115:20 am
SFO
- MDW
Nonstop4h 10m
Southwest
Deal found 6/10![Southwest logo]()
$345
This Southwest deal was found by Cheapflights users on 6/10. 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.
Tue 6/305:50 pm
MDW
- SFO
2 stops7h 25m
Southwest
Tue 7/712:10 pm
SFO
- MDW
1 stop8h 50m
Southwest
Deal found 6/10![Southwest logo]()
$354
This Southwest deal was found by Cheapflights users on 6/8. 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.
Fri 7/2411:50 am
MDW
- SFO
1 stop8h 25m
Southwest
Tue 7/2811:40 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Deal found 6/8![Southwest logo]()
$354
This Southwest deal was found by Cheapflights users on 6/7. 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.
Fri 7/109:30 pm
MDW
- SFO
Nonstop4h 45m
Southwest
Mon 7/206:10 pm
SFO
- MDW
1 stop8h 30m
Southwest
Deal found 6/7![Southwest logo]()
$354
This Southwest deal was found by Cheapflights users on 6/6. 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 8/109:30 pm
MDW
- SFO
Nonstop4h 35m
Southwest
Sat 8/1511:05 pm
SFO
- MDW
2 stops12h 40m
Southwest
Deal found 6/6![Southwest logo]()
$356
This Southwest deal was found by Cheapflights users on 6/7. 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.
Fri 7/172:15 pm
MDW
- SFO
1 stop6h 45m
Southwest
Tue 7/216:00 am
SFO
- MDW
2 stops8h 55m
Southwest
Deal found 6/7![Southwest logo]()
$369
This Southwest deal was found by Cheapflights users on 6/7. 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 6/299:30 pm
MDW
- SFO
Nonstop4h 40m
Southwest
Mon 7/611:40 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Deal found 6/7![Southwest logo]()
$371
Last-minute flights from Midway to San FranciscoDiscover last-minute flight deals from Midway to San Francisco. Data last updated June 11, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to San Francisco. Data last updated June 11, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 6/8. 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.
Thu 7/95:45 am
MDW
- SFO
1 stop7h 15m
Southwest
Tue 7/1411:40 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Deal found 6/8![Southwest logo]()
$304
This Expedia deal was found by Cheapflights users on 6/7. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/106:05 am
MDW
- SFO
1 stop15h 13m
Frontier
Sun 7/1210:10 pm
SFO
- MDW
1 stop10h 57m
Frontier
Deal found 6/7![Frontier logo]()
$305
This Frontier deal was found by Cheapflights users on 6/9. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/106:05 am
MDW
- SFO
1 stop15h 13m
Frontier
Sun 7/1910:10 pm
SFO
- MDW
1 stop10h 57m
Frontier
Deal found 6/9![Frontier logo]()
$309
This Frontier deal was found by Cheapflights users on 6/9. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/146:05 am
MDW
- SFO
1 stop15h 13m
Frontier
Mon 7/2011:00 pm
SFO
- MDW
1 stop10h 07m
Frontier
Deal found 6/9![Frontier logo]()
$301
This Southwest deal was found by Cheapflights users on 6/10. 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.
Wed 7/229:30 pm
MDW
- SFO
Nonstop4h 45m
Southwest
Sat 7/255:20 am
SFO
- MDW
Nonstop4h 10m
Southwest
Deal found 6/10![Southwest logo]()
$303
This Booking.com deal was found by Cheapflights users on 6/9. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/246:05 am
MDW
- SFO
1 stop15h 13m
Frontier
Fri 7/3111:00 pm
SFO
- MDW
1 stop10h 07m
Frontier
Deal found 6/9![Frontier logo]()
$308
This Frontier deal was found by Cheapflights users on 6/9. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/276:05 am
MDW
- SFO
1 stop15h 13m
Frontier
Thu 7/3010:10 pm
SFO
- MDW
1 stop10h 57m
Frontier
Deal found 6/9![Frontier logo]()
$307
This Southwest deal was found by Cheapflights users on 6/7. 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.
Wed 7/295:30 am
MDW
- SFO
1 stop6h 20m
Southwest
Tue 8/411:05 pm
SFO
- MDW
1 stop9h 50m
Southwest
Deal found 6/7![Southwest logo]()
$294
This Frontier deal was found by Cheapflights users on 6/8. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/296:05 am
MDW
- SFO
1 stop15h 13m
Frontier
Sun 8/210:10 pm
SFO
- MDW
1 stop10h 57m
Frontier
Deal found 6/8![Frontier logo]()
$306
This Trip.com deal was found by Cheapflights users on 6/10. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/306:05 am
MDW
- SFO
1 stop15h 13m
Frontier
Sun 8/210:10 pm
SFO
- MDW
1 stop10h 57m
Frontier
Deal found 6/10![Frontier logo]()
$298
This Southwest deal was found by Cheapflights users on 6/8. 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.
Thu 7/305:20 am
MDW
- SFO
2 stops8h 00m
Southwest
Wed 8/57:25 pm
SFO
- MDW
1 stop7h 05m
Southwest
Deal found 6/8![Southwest logo]()
$299
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 June 11, 2026.
Search for one-way flight options from Midway to San Francisco. Find affordable one-way fares based on user searches. Data last updated June 11, 2026.
This Frontier deal was found by Cheapflights users on 6/7. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/63:02 pm
MDW
- SFO
1 stop9h 55m
Frontier
Deal found 6/7![Frontier logo]()
$139
This Southwest deal was found by Cheapflights users on 6/9. 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 9/51:45 pm
MDW
- SFO
2 stops7h 50m
Southwest
Deal found 6/9![Southwest logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 6/9. 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 8/115:46 pm
MDW
- SFO
2 stops19h 36m
Frontier
Deal found 6/9![Frontier logo]()
$147
This Super.com deal was found by Cheapflights users on 6/10. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/212:27 pm
MDW
- SFO
1 stop8h 59m
Frontier
Deal found 6/10![Frontier logo]()
$148
This Super.com deal was found by Cheapflights users on 6/8. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/154:45 pm
MDW
- SFO
1 stop8h 14m
Frontier
Deal found 6/8![Frontier logo]()
$150
This Frontier deal was found by Cheapflights users on 6/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/1511:06 am
MDW
- SFO
1 stop10h 07m
Frontier
Deal found 6/10![Frontier logo]()
$152
This Super.com deal was found by Cheapflights users on 6/6. 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.
Fri 7/246:05 am
MDW
- SFO
1 stop15h 13m
Frontier
Deal found 6/6![Frontier logo]()
$157
This Super.com deal was found by Cheapflights users on 6/10. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/316:05 am
MDW
- SFO
1 stop15h 13m
Frontier
Deal found 6/10![Frontier logo]()
$158
This Trip.com deal was found by Cheapflights users on 6/7. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1012:11 pm
MDW
- SFO
1 stop9h 07m
Frontier
Deal found 6/7![Frontier logo]()
$159
This Orbitz deal was found by Cheapflights users on 6/9. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/236:00 am
MDW
- SFO
1 stop15h 25m
Frontier
Deal found 6/9![Frontier logo]()
$160
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 June 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $294 (Southwest) |
One-way from | $139 (Frontier) |
Popular in | February |
Cheapest in | April |
Average price | $383 |
Good round-trip deal | $311 or less |
Good one-way deal | $203 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 June 11, 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
Tue 8/4
5:10 pm-11:58 pm
1 stop8h 48m
San Francisco
Mon 8/10
12:12 am-8:39 am
1 stop6h 27m
$308
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Sat 7/4
9:54 am-4:24 pm
1 stop8h 30m
San Francisco
Mon 7/6
12:35 am-8:37 am
1 stop6h 02m
$314
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Sat 7/18
9:54 am-4:25 pm
1 stop8h 31m
San Francisco
Mon 7/20
12:35 am-8:37 am
1 stop6h 02m
$314
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Tue 7/14
6:10 am-1:40 pm
1 stop9h 30m
San Francisco
Sat 7/18
3:25 pm-12:10 am
1 stop6h 45m
$323
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Thu 9/17
5:30 am-11:35 am
1 stop8h 05m
San Francisco
Mon 9/21
5:35 am-11:40 am
Nonstop4h 05m
$345
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Thu 7/2
8:40 am-2:25 pm
1 stop7h 45m
San Francisco
Sat 7/11
5:20 am-11:30 am
Nonstop4h 10m
$345
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Tue 6/30
5:50 pm-11:15 pm
2 stops7h 25m
San Francisco
Tue 7/7
12:10 pm-11:00 pm
1 stop8h 50m
$354
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Fri 7/24
11:50 am-6:15 pm
1 stop8h 25m
San Francisco
Tue 7/28
11:40 pm-5:55 am
Nonstop4h 15m
$354
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Fri 7/10
9:30 pm-12:15 am
Nonstop4h 45m
San Francisco
Mon 7/20
6:10 pm-4:40 am
1 stop8h 30m
$354
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Mon 8/10
9:30 pm-12:05 am
Nonstop4h 35m
San Francisco
Sat 8/15
11:05 pm-1:45 pm
2 stops12h 40m
$356
Showing 1-10 of 24 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 June.
| 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 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, April is the cheapest month in which you can book a flight from Chicago Midway Airport to San Francisco (average of $288). Flying from Chicago Midway Airport to San Francisco in February is currently the most expensive (average of $635). 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 June 11, 2026.
It’s typically best to fly out from Chicago Midway Airport to San Francisco in the evening. Doing so could potentially save you 33% on the flight price compared to flying at noon, 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 June 8, 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 31% of weekly flights between Chicago and San Francisco have experienced delays in the past year, with the average delay time being 123 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 Friday 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 31% 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 June 11, 2026.
Read reviews from past customers who have flown Southwest 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
Comfort
8.0
Boarding
8.1
Food
7.0
Overall
7.9
Crew
8.6
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Food
7.0
Overall
7.9
Crew
8.6
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
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 Cruz
Santa Clara
Fairfield
Rancho Cordova
Roseville
Cupertino
Emeryville
Newark
San Bruno
Watsonville
San Ramon
Vacaville
San Carlos
Redwood City
Daly City
Sunnyvale
Turlock
Vallejo
San Lorenzo
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Midway and San Francisco flights
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Other flights to San Francisco
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Top airline flying from Midway to San Francisco
Discover the top airline 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 June 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$234 | Average$401 | FlexibilityNo cancel fee | On-time63% |