$119+ Cheap flights from Midway (MDW) to San Francisco Bay Area
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 5/5. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SFO
May 17 — May 241
Round-trip
1 adult, Economy
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Cheapest flights from Midway to San Francisco Bay AreaExplore the most affordable flight options available from Midway to San Francisco Bay Area. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 17, 2026.
Explore the most affordable flight options available from Midway to San Francisco Bay Area. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 17, 2026.
This Delta deal was found by Cheapflights users on 4/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/197:16 pm
MDW
- SFO
1 stop6h 37m
Delta
Tue 6/2310:59 pm
SFO
- MDW
1 stop9h 08m
Delta
Deal found 4/14![Delta logo]()
$243
This Orbitz deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/811:59 am
MDW
- SFO
1 stop9h 26m
Frontier
Sun 8/2311:52 pm
SFO
- MDW
1 stop12h 15m
Frontier
Deal found 4/12![Frontier logo]()
$244
This Delta deal was found by Cheapflights users on 4/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/281:24 pm
MDW
- SFO
1 stop7h 39m
Delta
Fri 5/111:59 pm
SFO
- MDW
1 stop7h 07m
Delta
Deal found 4/15![Delta logo]()
$245
This Delta deal was found by Cheapflights users on 4/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/259:27 am
MDW
- SFO
1 stop7h 28m
Delta
Wed 5/611:59 pm
SFO
- MDW
1 stop6h 43m
Delta
Deal found 4/15![Delta logo]()
$246
This Southwest deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/512:35 pm
MDW
- SFO
1 stop6h 55m
Southwest
Tue 5/511:25 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Deal found 4/13![Southwest logo]()
$247
This Southwest deal was found by Cheapflights users on 4/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/132:15 pm
MDW
- OAK
1 stop8h 05m
Southwest
Tue 5/1911:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Deal found 4/16![Southwest logo]()
$247
This Frontier deal was found by Cheapflights users on 4/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/96:00 am
MDW
- SFO
1 stop15h 26m
Frontier
Sun 6/2110:10 pm
SFO
- MDW
1 stop10h 59m
Frontier
Deal found 4/16![Frontier logo]()
$250
This Southwest deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/59:00 pm
MDW
- SFO
Nonstop4h 35m
Southwest
Mon 5/1111:25 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Deal found 4/13![Southwest logo]()
$251
This Southwest deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/68:50 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Sat 5/911:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Deal found 4/13![Southwest logo]()
$251
This Frontier deal was found by Cheapflights users on 4/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/16:00 am
MDW
- SFO
1 stop13h 34m
Frontier
Tue 5/511:59 pm
SFO
- MDW
1 stop12h 13m
Frontier
Deal found 4/16![Frontier logo]()
$252
This Frontier deal was found by Cheapflights users on 4/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/73:07 pm
MDW
- SFO
1 stop9h 57m
Frontier
Wed 5/1311:59 pm
SFO
- MDW
1 stop12h 13m
Frontier
Deal found 4/14![Frontier logo]()
$253
This Expedia deal was found by Cheapflights users on 4/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/36:00 am
MDW
- SFO
1 stop13h 34m
Frontier
Mon 5/410:38 pm
SFO
- MDW
1 stop10h 31m
Frontier
Deal found 4/14![Frontier logo]()
$255
Best flights from Midway to San Francisco Bay AreaDiscover carefully curated flight deals from Midway to San Francisco Bay Area that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 17, 2026.
Discover carefully curated flight deals from Midway to San Francisco Bay Area that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 17, 2026.
This Southwest deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/59:00 pm
MDW
- SFO
Nonstop4h 35m
Southwest
Sat 5/911:25 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Deal found 4/12![Southwest logo]()
$251
This Delta deal was found by Cheapflights users on 4/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/135:10 pm
MDW
- SJC
1 stop7h 50m
Delta
Sat 5/165:59 pm
SJC
- MDW
2 stops12h 44m
Delta
Deal found 4/16![Delta logo]()
$276
This Southwest deal was found by Cheapflights users on 4/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/25:35 pm
MDW
- SFO
1 stop7h 10m
Southwest
Sat 6/611:40 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Deal found 4/14![Southwest logo]()
$261
This Delta deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/91:59 pm
MDW
- SJC
1 stop8h 39m
Delta
Mon 5/118:50 pm
SJC
- MDW
2 stops9h 52m
Delta
Deal found 4/12![Delta logo]()
$290
This Southwest deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/49:30 pm
MDW
- SFO
Nonstop4h 40m
Southwest
Tue 6/95:10 am
SFO
- MDW
Nonstop4h 10m
Southwest
Deal found 4/13![Southwest logo]()
$265
This Southwest deal was found by Cheapflights users on 4/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/206:45 am
MDW
- SFO
1 stop7h 50m
Southwest
Wed 5/275:25 am
SFO
- MDW
Nonstop4h 10m
Southwest
Deal found 4/15![Southwest logo]()
$270
This Southwest deal was found by Cheapflights users on 4/17. 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
Tue 6/93:35 pm
SFO
- MDW
1 stop6h 30m
Southwest
Deal found 4/17![Southwest logo]()
$271
This Delta deal was found by Cheapflights users on 4/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/226:00 am
MDW
- SFO
1 stop9h 25m
Delta
Fri 10/29:30 pm
SFO
- MDW
1 stop10h 20m
Delta
Deal found 4/15![Delta logo]()
$330
This Southwest deal was found by Cheapflights users on 4/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/92:40 pm
MDW
- SJC
1 stop7h 10m
Southwest
Mon 5/1110:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Deal found 4/16![Southwest logo]()
$275
This Delta deal was found by Cheapflights users on 4/17. 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 6/109:17 am
MDW
- SJC
2 stops10h 00m
Delta
Sat 6/137:59 pm
SJC
- MDW
2 stops11h 15m
Delta
Deal found 4/17![Delta logo]()
$352
This Southwest deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/47:40 pm
MDW
- SFO
1 stop6h 30m
Southwest
Tue 5/126:20 am
SFO
- MDW
2 stops8h 15m
Southwest
Deal found 4/13![Southwest logo]()
$276
This Delta deal was found by Cheapflights users on 4/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/96:05 am
MDW
- SJC
1 stop7h 31m
Delta
Wed 8/56:35 am
SJC
- MDW
1 stop7h 40m
Delta
Deal found 4/16![Delta logo]()
$362
This Delta deal was found by Cheapflights users on 4/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/41:22 pm
MDW
- SJC
2 stops10h 52m
Delta
Sun 6/78:15 pm
SJC
- MDW
2 stops10h 22m
Delta
Deal found 4/14![Delta logo]()
$366
This Southwest deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/275:35 pm
MDW
- SFO
1 stop7h 10m
Southwest
Wed 6/311:25 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Deal found 4/12![Southwest logo]()
$305
This Southwest deal was found by Cheapflights users on 4/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/169:30 pm
MDW
- SFO
Nonstop4h 40m
Southwest
Tue 6/235:10 am
SFO
- MDW
Nonstop4h 10m
Southwest
Deal found 4/16![Southwest logo]()
$327
This Southwest deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/510:30 am
MDW
- SJC
2 stops7h 55m
Southwest
Wed 8/1911:00 pm
SJC
- MDW
Nonstop4h 00m
Southwest
Deal found 4/12![Southwest logo]()
$337
This Southwest deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/76:00 am
MDW
- SJC
2 stops7h 45m
Southwest
Sat 5/166:25 am
SJC
- MDW
2 stops8h 25m
Southwest
Deal found 4/12![Southwest logo]()
$340
This Southwest deal was found by Cheapflights users on 4/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/155:20 am
MDW
- SJC
1 stop6h 20m
Southwest
Tue 6/237:35 pm
SJC
- MDW
1 stop7h 05m
Southwest
Deal found 4/16![Southwest logo]()
$342
This Southwest deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/319:30 pm
MDW
- SFO
Nonstop4h 40m
Southwest
Mon 8/311:40 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Deal found 4/12![Southwest logo]()
$344
This Southwest deal was found by Cheapflights users on 4/17. 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 6/105:25 am
MDW
- SJC
2 stops8h 00m
Southwest
Sat 6/137:55 pm
SJC
- MDW
1 stop6h 45m
Southwest
Deal found 4/17![Southwest logo]()
$347
This Southwest deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/305:55 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Wed 6/311:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Deal found 4/13![Southwest logo]()
$353
This Southwest deal was found by Cheapflights users on 4/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/85:25 am
MDW
- OAK
1 stop7h 25m
Southwest
Sat 7/1111:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Deal found 4/16![Southwest logo]()
$354
This Southwest deal was found by Cheapflights users on 4/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/99:40 pm
MDW
- OAK
Nonstop4h 30m
Southwest
Fri 7/179:05 pm
OAK
- MDW
1 stop6h 20m
Southwest
Deal found 4/14![Southwest logo]()
$354
This Southwest deal was found by Cheapflights users on 4/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/156:00 am
MDW
- SJC
2 stops7h 45m
Southwest
Wed 5/2010:40 am
SJC
- MDW
1 stop6h 55m
Southwest
Deal found 4/14![Southwest logo]()
$367
This Southwest deal was found by Cheapflights users on 4/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/291:55 pm
MDW
- OAK
Nonstop4h 25m
Southwest
Mon 8/315:20 am
OAK
- MDW
Nonstop4h 05m
Southwest
Deal found 4/16![Southwest logo]()
$369
This Southwest deal was found by Cheapflights users on 4/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/306:00 am
MDW
- OAK
2 stops8h 25m
Southwest
Sun 6/145:05 am
OAK
- MDW
Nonstop4h 05m
Southwest
Deal found 4/15![Southwest logo]()
$371
This Southwest deal was found by Cheapflights users on 4/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/96:00 pm
MDW
- OAK
1 stop6h 25m
Southwest
Sat 7/187:50 pm
OAK
- MDW
1 stop7h 20m
Southwest
Deal found 4/14![Southwest logo]()
$380
This Southwest deal was found by Cheapflights users on 4/17. 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 9/183:55 pm
MDW
- OAK
1 stop7h 15m
Southwest
Sun 9/205:25 am
OAK
- MDW
Nonstop4h 05m
Southwest
Deal found 4/17![Southwest logo]()
$386
This Southwest deal was found by Cheapflights users on 4/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/112:15 pm
MDW
- OAK
2 stops7h 55m
Southwest
Sun 8/911:55 pm
OAK
- MDW
Nonstop4h 00m
Southwest
Deal found 4/14![Southwest logo]()
$411
This Southwest deal was found by Cheapflights users on 4/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/111:10 am
MDW
- OAK
2 stops8h 25m
Southwest
Tue 9/86:50 am
OAK
- MDW
2 stops7h 10m
Southwest
Deal found 4/16![Southwest logo]()
$415
Last-minute flights from Midway to San Francisco Bay AreaDiscover last-minute flight deals from Midway to San Francisco Bay Area. Data last updated April 17, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to San Francisco Bay Area. Data last updated April 17, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 4/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/259:27 am
MDW
- SFO
1 stop7h 28m
Delta
Mon 5/1112:15 am
SFO
- MDW
1 stop6h 27m
Delta
Deal found 4/15![Delta logo]()
$246
This Delta deal was found by Cheapflights users on 4/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/281:24 pm
MDW
- SFO
1 stop7h 39m
Delta
Fri 5/111:59 pm
SFO
- MDW
1 stop7h 07m
Delta
Deal found 4/15![Delta logo]()
$245
This Frontier deal was found by Cheapflights users on 4/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/16:00 am
MDW
- SFO
1 stop13h 34m
Frontier
Tue 5/511:59 pm
SFO
- MDW
1 stop12h 13m
Frontier
Deal found 4/16![Frontier logo]()
$252
This Expedia deal was found by Cheapflights users on 4/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/36:00 am
MDW
- SFO
1 stop13h 34m
Frontier
Mon 5/410:38 pm
SFO
- MDW
1 stop10h 31m
Frontier
Deal found 4/14![Frontier logo]()
$255
This Southwest deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/512:35 pm
MDW
- SFO
1 stop6h 55m
Southwest
Tue 5/511:25 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Deal found 4/13![Southwest logo]()
$247
This Southwest deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/59:00 pm
MDW
- SFO
Nonstop4h 35m
Southwest
Mon 5/1111:25 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Deal found 4/13![Southwest logo]()
$251
This Southwest deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/68:50 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Sat 5/911:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Deal found 4/13![Southwest logo]()
$251
This Frontier deal was found by Cheapflights users on 4/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/73:07 pm
MDW
- SFO
1 stop9h 57m
Frontier
Wed 5/1311:59 pm
SFO
- MDW
1 stop12h 13m
Frontier
Deal found 4/14![Frontier logo]()
$253
This Delta deal was found by Cheapflights users on 4/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/87:13 pm
MDW
- SFO
1 stop6h 37m
Delta
Sun 5/1011:59 pm
SFO
- MDW
1 stop8h 01m
Delta
Deal found 4/14![Delta logo]()
$256
This Delta deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/121:59 pm
MDW
- SFO
1 stop8h 38m
Delta
Mon 5/1812:15 am
SFO
- MDW
1 stop6h 27m
Delta
Deal found 4/12![Delta logo]()
$257
This Southwest deal was found by Cheapflights users on 4/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/132:15 pm
MDW
- OAK
1 stop8h 05m
Southwest
Tue 5/1911:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Deal found 4/16![Southwest logo]()
$247
This Frontier deal was found by Cheapflights users on 4/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:00 am
MDW
- SFO
1 stop15h 34m
Frontier
Wed 6/1010:10 pm
SFO
- MDW
1 stop11h 02m
Frontier
Deal found 4/14![Frontier logo]()
$250
One-way flights from Midway to San Francisco Bay AreaSearch for one-way flight options from Midway to San Francisco Bay Area. Find affordable one-way fares based on user searches. Data last updated April 17, 2026.
Search for one-way flight options from Midway to San Francisco Bay Area. Find affordable one-way fares based on user searches. Data last updated April 17, 2026.
This Southwest deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/510:00 am
MDW
- OAK
Nonstop4h 35m
Southwest
Deal found 4/13![Southwest logo]()
$119
This Frontier deal was found by Cheapflights users on 4/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/236:00 am
MDW
- SFO
1 stop13h 34m
Frontier
Deal found 4/14![Frontier logo]()
$132
This Southwest deal was found by Cheapflights users on 4/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/79:45 pm
MDW
- SFO
Nonstop4h 35m
Southwest
Deal found 4/16![Southwest logo]()
$133
This Southwest deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/149:50 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Deal found 4/13![Southwest logo]()
$133
This Southwest deal was found by Cheapflights users on 4/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/274:00 pm
MDW
- SFO
2 stops9h 15m
Southwest
Deal found 4/15![Southwest logo]()
$134
This Kissandfly.com deal was found by Cheapflights users on 4/16. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/296:10 am
MDW
- SFO
1 stop13h 24m
Frontier
Deal found 4/16![Frontier logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 4/17. 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 5/317:49 pm
MDW
- SFO
2 stops23h 18m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 4/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/303:27 pm
MDW
- SFO
1 stop26h 37m
Frontier
Deal found 4/14![Frontier logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 4/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/206:00 am
MDW
- SFO
2 stops15h 43m
Frontier
Deal found 4/14![Frontier logo]()
$139
This Frontier deal was found by Cheapflights users on 4/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/226:15 am
MDW
- SFO
1 stop13h 19m
Frontier
Deal found 4/16![Frontier logo]()
$141
This Kiwi.com deal was found by Cheapflights users on 4/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/16:00 am
MDW
- SFO
2 stops44h 23m
Frontier
Deal found 4/14![Frontier logo]()
$142
This Southwest deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/166:55 am
MDW
- SJC
1 stop8h 35m
Southwest
Deal found 4/13![Southwest logo]()
$143
Find flight deals from Midway to San Francisco Bay Area
Keep the following information in mind while searching for Midway to San Francisco Bay Area flight deals. Data was last updated April 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $243 (Delta) |
One-way from | $119 (Southwest) |
Popular in | February |
Cheapest in | September |
Average price | $365 |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to San Francisco Bay Area 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 April 17, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to San Francisco Bay Area that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Tue 5/5
9:00 pm-11:35 pm
Nonstop4h 35m
San Francisco
Sat 5/9
11:25 pm-5:40 am
Nonstop4h 15m
$251
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Tue 6/2
5:35 pm-10:45 pm
1 stop7h 10m
San Francisco
Sat 6/6
11:40 pm-5:55 am
Nonstop4h 15m
$261
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Thu 6/4
9:30 pm-12:10 am
Nonstop4h 40m
San Francisco
Tue 6/9
5:10 am-11:20 am
Nonstop4h 10m
$265
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Wed 5/20
6:45 am-12:35 pm
1 stop7h 50m
San Francisco
Wed 5/27
5:25 am-11:35 am
Nonstop4h 10m
$270
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Mon 6/1
6:25 pm-11:45 pm
1 stop7h 20m
San Francisco
Tue 6/9
3:35 pm-12:05 am
1 stop6h 30m
$271
ChicagoSan Jose
MDW - SJC
MDWSJC
Chicago Midway
Sat 5/9
2:40 pm-7:50 pm
1 stop7h 10m
San Jose
Mon 5/11
10:55 pm-5:00 am
Nonstop4h 05m
$275
ChicagoSan Jose
MDW - SJC
MDWSJC
Chicago Midway
Wed 5/13
5:10 pm-11:00 pm
1 stop7h 50m
San Jose
Sat 5/16
5:59 pm-8:43 am
2 stops12h 44m
$276
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Mon 5/4
7:40 pm-12:10 am
1 stop6h 30m
San Francisco
Tue 5/12
6:20 am-4:35 pm
2 stops8h 15m
$276
ChicagoSan Jose
MDW - SJC
MDWSJC
Chicago Midway
Sat 5/9
1:59 pm-8:38 pm
1 stop8h 39m
San Jose
Mon 5/11
8:50 pm-8:42 am
2 stops9h 52m
$290
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Wed 5/27
5:35 pm-10:45 pm
1 stop7h 10m
San Francisco
Wed 6/3
11:25 pm-5:40 am
Nonstop4h 15m
$305
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Midway to San Francisco Bay Area
Have a flexible travel schedule? Discover the best time to fly to San Francisco Bay Area from Midway with our price prediction graph.
MDW-OAK
MDW-SFO
MDW-SJC
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 Bay Area
MDW-zzXIH
MDW-OAK
MDW-SFO
MDW-SJC
What is the cheapest month to book a flight from Chicago Midway Airport to San Francisco Bay Area?
Currently, October is the cheapest month in which you can book a flight from Chicago Midway Airport to San Francisco Bay Area (average of $122). Flying from Chicago Midway Airport to San Francisco Bay Area in November is currently the most expensive (average of $309). 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 XIH?
Find hourly flight availability from Midway to San Francisco Bay Area. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 17, 2026.
Unlike in the morning, when flights are generally more expensive, you can save up to 26% on flights from Chicago Midway Airport to San Francisco Bay Area by exploring options for tickets in the afternoon.
What is the cheapest day to fly from Chicago Midway Airport to San Francisco Bay Area?
Use this chart to determine the cheapest time to fly round-trip from Midway to San Francisco Bay Area. Price data was last updated on April 11, 2026.
Travelers seeking maximum savings on their Chicago Midway Airport to San Francisco Bay Area flight should consider departing on Tuesday afternoons when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing San Francisco Bay Area
Get insights into the airlines that provide service to San Francisco Bay Area. 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 Bay Area. Reviews last updated April 17, 2026.
Read reviews from past customers who have flown Southwest from Chicago Midway Airport to San Francisco Bay Area. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Overall
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Overall
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from Midway to San Francisco Bay Area. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Complete your trip
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Search flights from Midway to San Francisco Bay Area by cabin class
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Midway and San Francisco Bay Area flights
Browse other Midway and San Francisco Bay Area flight options. Last updated on April 17, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top airline flying from Midway to San Francisco Bay Area
Discover the top airline that operate flights from Midway to San Francisco Bay Area. 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 April 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$231 | Average$441 | FlexibilityNo cancel fee | On-time63% |