$119+ Cheap flights from San Francisco Bay Area to Midway (MDW)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/12. Fares are subject to change and may not be available on all flights or dates of travel.
SFO — MDW
May 17 — May 241
Round-trip
1 adult, Economy
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Find cheap flights from San Francisco Bay Area to Midway with Cheapflights
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Cheapest flights from San Francisco Bay Area to MidwayExplore the most affordable flight options available from San Francisco Bay Area to Midway. 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 San Francisco Bay Area to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 17, 2026.
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 5/1911:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Tue 6/28:50 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Deal found 4/14![Southwest logo]()
$237
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
OAK
- MDW
1 stop6h 50m
Southwest
Tue 5/128:50 pm
MDW
- OAK
Nonstop4h 35m
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.
Sat 5/911:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Wed 5/138:50 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Deal found 4/13![Southwest logo]()
$251
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 5/138:15 am
OAK
- MDW
1 stop6h 45m
Southwest
Wed 5/204:30 pm
MDW
- OAK
1 stop6h 15m
Southwest
Deal found 4/15![Southwest logo]()
$257
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 5/1111:25 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Thu 5/149:45 pm
MDW
- SFO
Nonstop4h 35m
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.
Mon 5/1811:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Thu 5/219:50 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Deal found 4/15![Southwest logo]()
$265
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 5/286:20 am
SFO
- MDW
2 stops8h 45m
Southwest
Tue 6/99:30 pm
MDW
- SFO
Nonstop4h 40m
Southwest
Deal found 4/13![Southwest logo]()
$266
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.
Sat 5/25:40 am
SFO
- MDW
2 stops9h 35m
Southwest
Sat 5/96:45 am
MDW
- SFO
1 stop7h 50m
Southwest
Deal found 4/12![Southwest logo]()
$267
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/197:00 am
SJC
- MDW
2 stops12h 09m
Delta
Tue 6/169:54 am
MDW
- SJC
2 stops9h 23m
Delta
Deal found 4/13![Delta logo]()
$267
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 5/135:25 am
SFO
- MDW
Nonstop4h 10m
Southwest
Tue 5/196:45 am
MDW
- SFO
1 stop7h 50m
Southwest
Deal found 4/16![Southwest logo]()
$270
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.
Wed 5/2012:15 am
SFO
- MDW
1 stop6h 27m
Delta
Mon 6/11:59 pm
MDW
- SFO
1 stop8h 34m
Delta
Deal found 4/15![Delta logo]()
$271
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 5/279:25 pm
SJC
- MDW
1 stop6h 00m
Southwest
Sat 5/3010:00 am
MDW
- SJC
1 stop7h 10m
Southwest
Deal found 4/13![Southwest logo]()
$271
Best flights from San Francisco Bay Area to MidwayDiscover carefully curated flight deals from San Francisco Bay Area to Midway 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 San Francisco Bay Area to Midway 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.
Mon 5/1111:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Tue 5/128:50 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Deal found 4/12![Southwest logo]()
$251
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 8/1812:40 am
SFO
- MDW
1 stop5h 58m
Delta
Sun 8/236:00 am
MDW
- SFO
1 stop9h 21m
Delta
Deal found 4/15![Delta logo]()
$283
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 5/411:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Tue 5/127:30 am
MDW
- OAK
1 stop8h 00m
Southwest
Deal found 4/13![Southwest logo]()
$261
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 5/98:05 am
OAK
- MDW
1 stop7h 45m
Southwest
Wed 5/138:50 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Deal found 4/15![Southwest logo]()
$261
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 5/97:10 am
SJC
- MDW
1 stop7h 22m
Delta
Sat 5/169:23 am
MDW
- SJC
2 stops8h 46m
Delta
Deal found 4/15![Delta logo]()
$290
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.
Thu 5/288:55 pm
OAK
- MDW
1 stop6h 05m
Southwest
Tue 6/22:55 pm
MDW
- OAK
1 stop7h 40m
Southwest
Deal found 4/15![Southwest logo]()
$271
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.
Tue 8/185:55 am
OAK
- MDW
2 stops13h 51m
Delta
Sat 8/229:20 am
MDW
- OAK
2 stops9h 11m
Delta
Deal found 4/14![Delta logo]()
$301
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.
Fri 6/512:15 am
SFO
- MDW
1 stop6h 27m
Delta
Mon 6/85:11 pm
MDW
- SFO
2 stops30h 14m
Delta
Deal found 4/16![Delta logo]()
$310
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.
Sat 5/1611:25 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Wed 5/205:30 am
MDW
- SFO
1 stop7h 35m
Southwest
Deal found 4/12![Southwest logo]()
$284
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.
Wed 6/106:35 am
SJC
- MDW
1 stop7h 41m
Delta
Wed 6/241:49 pm
MDW
- SJC
1 stop8h 50m
Delta
Deal found 4/15![Delta logo]()
$318
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 5/285:15 am
SFO
- MDW
Nonstop4h 10m
Southwest
Mon 6/19:45 pm
MDW
- SFO
Nonstop4h 35m
Southwest
Deal found 4/16![Southwest logo]()
$300
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 5/1311:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Wed 5/204:30 pm
MDW
- OAK
1 stop6h 15m
Southwest
Deal found 4/15![Southwest logo]()
$313
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.
Mon 9/2112:40 am
SFO
- MDW
1 stop5h 58m
Delta
Mon 9/285:25 pm
MDW
- SFO
1 stop8h 37m
Delta
Deal found 4/14![Delta logo]()
$355
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
SFO
- MDW
1 stop9h 55m
Southwest
Thu 5/149:45 pm
MDW
- SFO
Nonstop4h 35m
Southwest
Deal found 4/12![Southwest logo]()
$316
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 5/198:50 pm
SJC
- MDW
2 stops9h 52m
Delta
Tue 5/266:23 am
MDW
- SJC
2 stops11h 09m
Delta
Deal found 4/15![Delta logo]()
$388
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 5/305:40 am
SFO
- MDW
2 stops9h 35m
Southwest
Sat 6/610:25 am
MDW
- SFO
1 stop8h 50m
Southwest
Deal found 4/15![Southwest logo]()
$334
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 6/179:00 pm
OAK
- MDW
1 stop6h 25m
Southwest
Sat 7/1110:15 am
MDW
- OAK
2 stops8h 10m
Southwest
Deal found 4/13![Southwest logo]()
$336
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.
Sun 5/38:20 pm
SJC
- MDW
2 stops10h 27m
Delta
Sat 5/91:59 pm
MDW
- SJC
1 stop8h 39m
Delta
Deal found 4/12![Delta logo]()
$407
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 9/236:35 am
SFO
- MDW
2 stops7h 25m
Southwest
Wed 9/238:30 pm
MDW
- SFO
Nonstop4h 35m
Southwest
Deal found 4/16![Southwest logo]()
$350
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/196:35 am
SJC
- MDW
1 stop7h 40m
Delta
Fri 7/246:05 am
MDW
- SJC
2 stops13h 07m
Delta
Deal found 4/13![Delta logo]()
$432
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 4/295:50 am
OAK
- MDW
Nonstop4h 05m
Southwest
Tue 5/1211:00 am
MDW
- OAK
1 stop7h 50m
Southwest
Deal found 4/16![Southwest logo]()
$350
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/128:15 pm
SJC
- MDW
2 stops10h 22m
Delta
Sat 8/16:05 am
MDW
- SJC
1 stop7h 25m
Delta
Deal found 4/13![Delta logo]()
$432
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 6/153:45 pm
SFO
- MDW
1 stop7h 40m
Southwest
Tue 6/238:40 am
MDW
- SFO
1 stop9h 05m
Southwest
Deal found 4/16![Southwest logo]()
$351
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 5/2311:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Tue 5/263:55 pm
MDW
- OAK
1 stop6h 25m
Southwest
Deal found 4/13![Southwest logo]()
$352
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 6/1511:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Tue 6/239:00 pm
MDW
- OAK
Nonstop4h 30m
Southwest
Deal found 4/16![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.
Fri 8/2111:55 pm
OAK
- MDW
Nonstop4h 00m
Southwest
Mon 8/246:15 pm
MDW
- OAK
1 stop6h 30m
Southwest
Deal found 4/16![Southwest logo]()
$363
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 5/611:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Sat 5/910:00 am
MDW
- OAK
1 stop8h 55m
Southwest
Deal found 4/16![Southwest logo]()
$364
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 6/173:10 pm
SFO
- MDW
1 stop6h 55m
Southwest
Sat 7/115:10 pm
MDW
- SFO
2 stops7h 15m
Southwest
Deal found 4/13![Southwest logo]()
$365
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.
Tue 6/910:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Tue 6/238:55 pm
MDW
- SJC
Nonstop4h 30m
Southwest
Deal found 4/15![Southwest logo]()
$387
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.
Sun 5/319:20 pm
SJC
- MDW
1 stop5h 40m
Southwest
Tue 6/27:30 am
MDW
- SJC
2 stops8h 15m
Southwest
Deal found 4/13![Southwest logo]()
$392
Last-minute flights from San Francisco Bay Area to MidwayDiscover last-minute flight deals from San Francisco Bay Area to Midway. Data last updated April 17, 2026 and is based on user searches.
Discover last-minute flight deals from San Francisco Bay Area to Midway. Data last updated April 17, 2026 and is based on user searches.
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.
Sat 5/25:40 am
SFO
- MDW
2 stops9h 35m
Southwest
Sat 5/96:45 am
MDW
- SFO
1 stop7h 50m
Southwest
Deal found 4/12![Southwest logo]()
$267
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
OAK
- MDW
1 stop6h 50m
Southwest
Tue 5/128:50 pm
MDW
- OAK
Nonstop4h 35m
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.
Sat 5/911:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Wed 5/138:50 pm
MDW
- OAK
Nonstop4h 35m
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.
Mon 5/1111:25 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Thu 5/149:45 pm
MDW
- SFO
Nonstop4h 35m
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 5/138:15 am
OAK
- MDW
1 stop6h 45m
Southwest
Wed 5/204:30 pm
MDW
- OAK
1 stop6h 15m
Southwest
Deal found 4/15![Southwest 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 5/135:25 am
SFO
- MDW
Nonstop4h 10m
Southwest
Tue 5/196:45 am
MDW
- SFO
1 stop7h 50m
Southwest
Deal found 4/16![Southwest logo]()
$270
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.
Mon 5/1811:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Thu 5/219:50 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Deal found 4/15![Southwest logo]()
$265
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 5/1911:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Tue 6/28:50 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Deal found 4/14![Southwest logo]()
$237
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/197:00 am
SJC
- MDW
2 stops12h 09m
Delta
Wed 6/106:05 am
MDW
- SJC
2 stops13h 12m
Delta
Deal found 4/13![Delta logo]()
$267
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.
Wed 5/2012:15 am
SFO
- MDW
1 stop6h 27m
Delta
Wed 6/35:15 pm
MDW
- SFO
1 stop8h 09m
Delta
Deal found 4/15![Delta logo]()
$271
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 5/279:25 pm
SJC
- MDW
1 stop6h 00m
Southwest
Sat 5/3010:00 am
MDW
- SJC
1 stop7h 10m
Southwest
Deal found 4/13![Southwest logo]()
$271
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 5/286:20 am
SFO
- MDW
2 stops8h 45m
Southwest
Tue 6/99:30 pm
MDW
- SFO
Nonstop4h 40m
Southwest
Deal found 4/13![Southwest logo]()
$266
One-way flights from San Francisco Bay Area to MidwaySearch for one-way flight options from San Francisco Bay Area to Midway. Find affordable one-way fares based on user searches. Data last updated April 17, 2026.
Search for one-way flight options from San Francisco Bay Area to Midway. 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 5/2611:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Deal found 4/13![Southwest logo]()
$119
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/185:25 pm
SFO
- MDW
2 stops18h 47m
Frontier
Deal found 4/15![Frontier logo]()
$127
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 5/135:40 am
SFO
- MDW
1 stop8h 15m
Southwest
Deal found 4/16![Southwest logo]()
$129
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 5/139:05 pm
OAK
- MDW
1 stop5h 55m
Southwest
Deal found 4/13![Southwest logo]()
$129
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.
Sat 5/163:26 pm
SFO
- MDW
2 stops20h 46m
Frontier
Deal found 4/14![Frontier logo]()
$130
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.
Tue 5/512:52 pm
SFO
- MDW
2 stops31h 10m
Frontier
Deal found 4/14![Frontier logo]()
$131
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.
Sun 8/2311:52 pm
SFO
- MDW
1 stop12h 15m
Frontier
Deal found 4/14![Frontier logo]()
$132
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 5/115:15 am
SFO
- MDW
Nonstop4h 10m
Southwest
Deal found 4/13![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.
Mon 5/1111:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Deal found 4/13![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.
Wed 6/245:00 am
SFO
- MDW
2 stops7h 35m
Southwest
Deal found 4/13![Southwest logo]()
$134
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 5/610:45 am
OAK
- MDW
2 stops7h 10m
Southwest
Deal found 4/15![Southwest logo]()
$134
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/116:00 am
SFO
- MDW
2 stops27h 09m
Frontier
Deal found 4/16![Frontier logo]()
$135
Find flight deals from San Francisco Bay Area to Midway
Keep the following information in mind while searching for San Francisco Bay Area to Midway flight deals. Data was last updated April 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $237 (Southwest) |
One-way from | $119 (Southwest) |
Popular in | March |
Cheapest in | September |
Average price | $374 |
Cheapflights Fare Finder
Customize your flight search to find flights from San Francisco Bay Area to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 17, 2026.
Use the filters below to find and compare flights from San Francisco Bay Area to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
OaklandChicago
OAK - MDW
OAKMDW
Oakland
Mon 5/11
11:55 pm-6:00 am
Nonstop4h 05m
Chicago Midway
Tue 5/12
8:50 pm-11:25 pm
Nonstop4h 35m
$251
OaklandChicago
OAK - MDW
OAKMDW
Oakland
Mon 5/4
11:55 pm-6:00 am
Nonstop4h 05m
Chicago Midway
Tue 5/12
7:30 am-1:30 pm
1 stop8h 00m
$261
OaklandChicago
OAK - MDW
OAKMDW
Oakland
Sat 5/9
8:05 am-5:50 pm
1 stop7h 45m
Chicago Midway
Wed 5/13
8:50 pm-11:25 pm
Nonstop4h 35m
$261
OaklandChicago
OAK - MDW
OAKMDW
Oakland
Thu 5/28
8:55 pm-5:00 am
1 stop6h 05m
Chicago Midway
Tue 6/2
2:55 pm-8:35 pm
1 stop7h 40m
$271
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Tue 8/18
12:40 am-8:38 am
1 stop5h 58m
Chicago Midway
Sun 8/23
6:00 am-1:21 pm
1 stop9h 21m
$283
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Sat 5/16
11:25 pm-5:40 am
Nonstop4h 15m
Chicago Midway
Wed 5/20
5:30 am-11:05 am
1 stop7h 35m
$284
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Sat 5/9
7:10 am-4:32 pm
1 stop7h 22m
Chicago Midway
Sat 5/16
9:23 am-4:09 pm
2 stops8h 46m
$290
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Thu 5/28
5:15 am-11:25 am
Nonstop4h 10m
Chicago Midway
Mon 6/1
9:45 pm-12:20 am
Nonstop4h 35m
$300
OaklandChicago
OAK - MDW
OAKMDW
Oakland
Tue 8/18
5:55 am-9:46 pm
2 stops13h 51m
Chicago Midway
Sat 8/22
9:20 am-4:31 pm
2 stops9h 11m
$301
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Fri 6/5
12:15 am-8:42 am
1 stop6h 27m
Chicago Midway
Mon 6/8
5:11 pm-9:25 pm
2 stops30h 14m
$310
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from San Francisco Bay Area to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from San Francisco Bay Area with our price prediction graph.
OAK-MDW
SJC-MDW
SFO-MDW
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from San Francisco Bay Area to Chicago Midway Airport
zzXIH-MDW
OAK-MDW
SJC-MDW
SFO-MDW
What is the cheapest month to book a flight from San Francisco Bay Area to Chicago Midway Airport?
Currently, January is the cheapest month in which you can book a flight from San Francisco Bay Area to Chicago Midway Airport (average of $118). Flying from San Francisco Bay Area to Chicago Midway Airport in December is currently the most expensive (average of $239). 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 XIH to MDW?
Find hourly flight availability from San Francisco Bay Area to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 17, 2026.
It’s optimal to fly from San Francisco Bay Area to Chicago Midway Airport in the afternoon. By choosing this option you can save up to 43% on the cost of your flight, compared to a flight at noon.
What is the cheapest day to fly from San Francisco Bay Area to Chicago Midway Airport?
Use this chart to determine the cheapest time to fly round-trip from San Francisco Bay Area to Midway. Price data was last updated on April 11, 2026.
Travelers seeking maximum savings on their San Francisco Bay Area to Chicago Midway Airport flight should consider departing on Saturday afternoons when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from San Francisco Bay Area to Chicago Midway Airport
Explore weekly flight availability from San Francisco Bay Area to Midway. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated April 17, 2026.
The most flights from zzXIH to MDW are scheduled on a Monday (2 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (1 on average).
Reviews of airlines servicing Midway
Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated April 17, 2026.
See what other customers who have flown with Southwest,Delta, andUnited Airlines from San Francisco Bay Area to Chicago Midway Airport have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Boarding
8.1
Entertainment
7.5
Overall
8.0
Comfort
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Crew
8.6
Boarding
8.1
Entertainment
7.5
Overall
8.0
Comfort
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Crew
8.6
Boarding
8.1
Entertainment
7.5
Overall
8.0
Comfort
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Crew
8.6
Boarding
8.1
Entertainment
7.5
Overall
8.0
Comfort
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Crew
8.6
Boarding
8.1
Entertainment
7.5
Overall
8.0
Comfort
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Related info for your journey
Find useful and relevant information for your journey from San Francisco Bay Area to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Hammond
Porter
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Alternative routes for San Francisco Bay Area to Midway
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Complete your trip
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Search flights from San Francisco Bay Area to Midway by cabin class
Find flights from San Francisco Bay Area to Midway, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Other flights to Midway
Explore flights to Midway departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on April 17, 2026.
San Francisco Bay Area and Midway flights
Browse other San Francisco Bay Area and Midway flight options. Last updated on April 17, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 4 airlines flying from San Francisco Bay Area to Midway
Discover the top 4 airlines that operate flights from San Francisco Bay Area to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$133 | Average$450 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$147 | Average$237 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$241 | Average$358 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$250 | Average$475 | FlexibilityNo cancel fee | On-time63% |