$89+ 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 5/19. Fares are subject to change and may not be available on all flights or dates of travel.
SFO — MDW
Mar 30 — Apr 61
1 adult, Economy
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Find cheap flights from San Francisco Bay Area to Midway with Cheapflights
1. Tell us where you want to go
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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 February 28, 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 February 28, 2026.
This Southwest deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/1311:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Mon 4/209:50 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Deal found 2/25![Southwest logo]()
$177
This Southwest deal was found by Cheapflights users on 2/26. 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 4/2811:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Sat 5/25:55 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Deal found 2/26![Southwest logo]()
$211
This Southwest deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2711:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Tue 4/288:50 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Deal found 2/26![Southwest logo]()
$218
This Southwest deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/225:45 am
OAK
- MDW
2 stops7h 20m
Southwest
Fri 4/249:50 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Deal found 2/25![Southwest logo]()
$219
This Southwest deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/215:45 am
OAK
- MDW
2 stops7h 20m
Southwest
Thu 4/239:50 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Deal found 2/24![Southwest logo]()
$225
This Kiwi.com deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/311:16 pm
SFO
- MDW
2 stops18h 15m
Frontier
Fri 5/86:15 am
MDW
- SFO
1 stop13h 31m
Frontier
Deal found 2/25![Frontier logo]()
$229
This Southwest deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/208:30 pm
OAK
- MDW
1 stop6h 55m
Southwest
Tue 4/2110:10 am
MDW
- OAK
2 stops7h 50m
Southwest
Deal found 2/25![Southwest logo]()
$229
This Southwest deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/217:40 pm
SFO
- MDW
1 stop6h 55m
Southwest
Tue 4/289:00 pm
MDW
- SFO
Nonstop4h 35m
Southwest
Deal found 2/25![Southwest logo]()
$232
This Southwest deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/185:40 am
SFO
- MDW
2 stops9h 35m
Southwest
Sat 4/2510:05 am
MDW
- SFO
2 stops9h 10m
Southwest
Deal found 2/28![Southwest logo]()
$233
This Southwest deal was found by Cheapflights users on 2/28. 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 5/211:25 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Tue 5/53:00 pm
MDW
- SFO
1 stop7h 55m
Southwest
Deal found 2/28![Southwest logo]()
$234
This Southwest deal was found by Cheapflights users on 2/26. 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 5/65:25 am
SFO
- MDW
Nonstop4h 10m
Southwest
Sat 5/96:10 pm
MDW
- SFO
Nonstop4h 35m
Southwest
Deal found 2/26![Southwest logo]()
$236
This Delta deal was found by Cheapflights users on 2/28. 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 5/26:00 am
SFO
- MDW
1 stop8h 26m
Delta
Tue 5/56:00 am
MDW
- SFO
1 stop8h 33m
Delta
Deal found 2/28![Delta logo]()
$237
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 February 28, 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 February 28, 2026.
This Southwest deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/55:45 am
OAK
- MDW
2 stops7h 20m
Southwest
Fri 5/86:55 am
MDW
- OAK
1 stop7h 15m
Southwest
Deal found 2/25![Southwest logo]()
$229
This Delta deal was found by Cheapflights users on 2/26. 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 4/2110:55 pm
SFO
- MDW
1 stop7h 52m
Delta
Sat 4/251:24 pm
MDW
- SFO
1 stop7h 39m
Delta
Deal found 2/26![Delta logo]()
$237
This Southwest deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/2511:55 pm
OAK
- MDW
Nonstop4h 00m
Southwest
Wed 4/19:00 pm
MDW
- OAK
Nonstop4h 40m
Southwest
Deal found 2/25![Southwest logo]()
$247
This Delta deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/610:55 pm
SFO
- MDW
1 stop7h 48m
Delta
Wed 5/1312:51 pm
MDW
- SFO
1 stop9h 50m
Delta
Deal found 2/25![Delta logo]()
$278
This Southwest deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/115:50 am
OAK
- MDW
Nonstop4h 05m
Southwest
Thu 3/199:30 pm
MDW
- OAK
Nonstop4h 40m
Southwest
Deal found 2/25![Southwest logo]()
$272
This Delta deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/88:45 pm
SJC
- MDW
2 stops9h 57m
Delta
Mon 5/119:22 am
MDW
- SJC
2 stops9h 53m
Delta
Deal found 2/24![Delta logo]()
$312
This Southwest deal was found by Cheapflights users on 2/27. 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 4/245:15 am
SFO
- MDW
Nonstop4h 10m
Southwest
Mon 4/279:45 pm
MDW
- SFO
Nonstop4h 35m
Southwest
Deal found 2/27![Southwest logo]()
$285
This Southwest deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/76:20 am
SFO
- MDW
2 stops8h 15m
Southwest
Mon 4/134:10 pm
MDW
- SFO
2 stops8h 00m
Southwest
Deal found 2/24![Southwest logo]()
$288
This Delta deal was found by Cheapflights users on 2/28. 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 8/185:05 pm
OAK
- MDW
2 stops14h 45m
Delta
Sat 8/229:20 am
MDW
- OAK
2 stops9h 11m
Delta
Deal found 2/28![Delta logo]()
$343
This Southwest deal was found by Cheapflights users on 2/28. 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 5/1811:25 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Fri 5/229:45 pm
MDW
- SFO
Nonstop4h 35m
Southwest
Deal found 2/28![Southwest logo]()
$309
This Delta deal was found by Cheapflights users on 2/27. 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 4/248:20 pm
SJC
- MDW
2 stops10h 46m
Delta
Tue 4/289:29 am
MDW
- SJC
2 stops11h 38m
Delta
Deal found 2/27![Delta logo]()
$390
This Southwest deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/710:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Fri 4/105:25 am
MDW
- SJC
1 stop6h 55m
Southwest
Deal found 2/25![Southwest logo]()
$324
This Southwest deal was found by Cheapflights users on 2/27. 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 5/2811:25 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Tue 6/26:45 am
MDW
- SFO
1 stop7h 50m
Southwest
Deal found 2/27![Southwest logo]()
$325
This Delta deal was found by Cheapflights users on 2/27. 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 5/18:20 pm
SJC
- MDW
2 stops10h 46m
Delta
Sun 5/101:22 pm
MDW
- SJC
2 stops10h 52m
Delta
Deal found 2/27![Delta logo]()
$417
This Southwest deal was found by Cheapflights users on 2/28. 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 4/108:50 am
SFO
- MDW
1 stop7h 15m
Southwest
Mon 4/135:10 am
MDW
- SFO
1 stop6h 20m
Southwest
Deal found 2/28![Southwest logo]()
$329
This Delta deal was found by Cheapflights users on 2/27. 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 5/299:55 pm
SFO
- MDW
1 stop10h 04m
Delta
Sun 5/317:13 pm
MDW
- SFO
1 stop6h 37m
Delta
Deal found 2/27![Delta logo]()
$425
This Southwest deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/2411:25 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Mon 6/19:45 pm
MDW
- SFO
Nonstop4h 35m
Southwest
Deal found 2/25![Southwest logo]()
$351
This Delta deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2810:55 pm
SJC
- MDW
1 stop7h 48m
Delta
Mon 6/11:59 pm
MDW
- SJC
1 stop8h 39m
Delta
Deal found 2/24![Delta logo]()
$427
This Southwest deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/611:25 pm
SFO
- MDW
Nonstop4h 05m
Southwest
Sat 4/116:45 am
MDW
- SFO
1 stop7h 50m
Southwest
Deal found 2/24![Southwest logo]()
$355
This Southwest deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/301:25 pm
OAK
- MDW
1 stop7h 15m
Southwest
Sun 5/35:10 am
MDW
- OAK
1 stop6h 45m
Southwest
Deal found 2/24![Southwest logo]()
$360
This Southwest deal was found by Cheapflights users on 2/26. 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 5/1010:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Fri 5/158:25 pm
MDW
- SJC
Nonstop4h 35m
Southwest
Deal found 2/26![Southwest logo]()
$369
This Southwest deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/239:35 pm
SJC
- MDW
1 stop5h 45m
Southwest
Thu 3/2610:00 am
MDW
- SJC
1 stop6h 10m
Southwest
Deal found 2/24![Southwest logo]()
$385
This Southwest deal was found by Cheapflights users on 2/28. 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 6/2810:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Sat 7/410:30 am
MDW
- SJC
Nonstop4h 25m
Southwest
Deal found 2/28![Southwest logo]()
$387
This Southwest deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/3010:10 am
SFO
- MDW
1 stop9h 25m
Southwest
Sun 5/39:35 pm
MDW
- SFO
Nonstop4h 35m
Southwest
Deal found 2/24![Southwest logo]()
$399
This Southwest deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/12:50 pm
SJC
- MDW
1 stop7h 05m
Southwest
Fri 6/510:00 am
MDW
- SJC
1 stop7h 00m
Southwest
Deal found 2/24![Southwest logo]()
$407
This Southwest deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/174:20 pm
SJC
- MDW
1 stop5h 55m
Southwest
Wed 7/225:25 am
MDW
- SJC
2 stops8h 00m
Southwest
Deal found 2/25![Southwest logo]()
$408
This Southwest deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/178:55 pm
SJC
- MDW
1 stop6h 45m
Southwest
Mon 6/225:20 am
MDW
- SJC
1 stop6h 20m
Southwest
Deal found 2/24![Southwest logo]()
$427
This Southwest deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/289:25 pm
SJC
- MDW
1 stop5h 55m
Southwest
Wed 4/16:05 am
MDW
- SJC
1 stop8h 00m
Southwest
Deal found 2/24![Southwest logo]()
$427
This Southwest deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/286:50 am
OAK
- MDW
2 stops8h 15m
Southwest
Tue 3/319:10 am
MDW
- OAK
2 stops8h 35m
Southwest
Deal found 2/24![Southwest logo]()
$528
This Southwest deal was found by Cheapflights users on 2/27. 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 5/215:55 am
OAK
- MDW
Nonstop4h 05m
Southwest
Mon 5/257:40 pm
MDW
- OAK
1 stop6h 25m
Southwest
Deal found 2/27![Southwest logo]()
$556
Last-minute flights from San Francisco Bay Area to MidwayDiscover last-minute flight deals from San Francisco Bay Area to Midway. Data last updated February 28, 2026 and is based on user searches.
Discover last-minute flight deals from San Francisco Bay Area to Midway. Data last updated February 28, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1711:25 pm
SFO
- MDW
Nonstop4h 05m
Southwest
Wed 3/189:05 pm
MDW
- SFO
Nonstop4h 40m
Southwest
Deal found 2/24![Southwest logo]()
$253
This Southwest deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/185:40 am
SFO
- MDW
Nonstop4h 00m
Southwest
Wed 3/256:05 am
MDW
- SFO
1 stop9h 40m
Southwest
Deal found 2/24![Southwest logo]()
$263
This Southwest deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/2511:55 pm
OAK
- MDW
Nonstop4h 00m
Southwest
Wed 4/19:00 pm
MDW
- OAK
Nonstop4h 40m
Southwest
Deal found 2/25![Southwest logo]()
$247
This Southwest deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/255:40 am
SFO
- MDW
Nonstop4h 00m
Southwest
Wed 4/15:55 am
MDW
- SFO
1 stop6h 25m
Southwest
Deal found 2/25![Southwest logo]()
$255
This Southwest deal was found by Cheapflights users on 2/28. 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 3/255:40 am
SFO
- MDW
Nonstop4h 00m
Southwest
Wed 3/255:50 pm
MDW
- SFO
1 stop7h 25m
Southwest
Deal found 2/28![Southwest logo]()
$261
This Delta deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/3010:40 pm
SFO
- MDW
1 stop8h 13m
Delta
Wed 4/11:10 pm
MDW
- SFO
1 stop7h 57m
Delta
Deal found 2/24![Delta logo]()
$260
This Delta deal was found by Cheapflights users on 2/27. 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 3/3010:40 pm
SFO
- MDW
1 stop8h 13m
Delta
Fri 4/37:20 pm
MDW
- SFO
1 stop6h 42m
Delta
Deal found 2/27![Delta logo]()
$265
This Southwest deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/3011:25 pm
SFO
- MDW
Nonstop4h 05m
Southwest
Wed 4/19:05 pm
MDW
- SFO
Nonstop4h 40m
Southwest
Deal found 2/25![Southwest logo]()
$271
This Delta deal was found by Cheapflights users on 2/27. 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 3/3110:40 pm
SFO
- MDW
1 stop8h 13m
Delta
Tue 4/79:35 am
MDW
- SFO
1 stop7h 07m
Delta
Deal found 2/27![Delta logo]()
$237
This Southwest deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/315:40 am
SFO
- MDW
Nonstop4h 00m
Southwest
Sat 4/49:40 pm
MDW
- SFO
Nonstop4h 40m
Southwest
Deal found 2/25![Southwest logo]()
$245
This Delta deal was found by Cheapflights users on 2/27. 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 3/3110:40 pm
SFO
- MDW
1 stop8h 13m
Delta
Sun 4/59:35 am
MDW
- SFO
1 stop7h 07m
Delta
Deal found 2/27![Delta logo]()
$251
This Delta deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/3110:40 pm
SFO
- MDW
1 stop8h 13m
Delta
Sat 4/49:35 am
MDW
- SFO
1 stop7h 07m
Delta
Deal found 2/24![Delta logo]()
$257
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 February 28, 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 February 28, 2026.
This Southwest deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
Deal found 2/25![Southwest logo]()
$89
This Kiwi.com deal was found by Cheapflights users on 2/28. 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 5/125:47 pm
SFO
- MDW
2 stops43h 02m
Frontier
Deal found 2/28![Frontier logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/210:38 pm
SFO
- MDW
1 stop21h 41m
Frontier
Deal found 2/25![Frontier logo]()
$110
This Kiwi.com deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/206:00 am
SFO
- MDW
2 stops35h 31m
Frontier
Deal found 2/27![Frontier logo]()
$111
This Kiwi.com deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/1510:38 pm
SFO
- MDW
1 stop21h 41m
Frontier
Deal found 2/27![Frontier logo]()
$112
This Kiwi.com deal was found by Cheapflights users on 2/26. 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 4/166:00 am
SFO
- MDW
2 stops14h 19m
Frontier
Deal found 2/26![Frontier logo]()
$113
This Southwest deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/711:25 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Deal found 2/24![Southwest logo]()
$115
This Southwest deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/711:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Deal found 2/25![Southwest logo]()
$115
This Kiwi.com deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/227:40 pm
SFO
- MDW
2 stops24h 42m
Frontier
Deal found 2/25![Frontier logo]()
$116
This Southwest deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/185:40 am
SFO
- MDW
2 stops9h 35m
Southwest
Deal found 2/28![Southwest logo]()
$117
This Trip.com deal was found by Cheapflights users on 2/28. 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 5/110:38 pm
SFO
- MDW
1 stop21h 36m
Frontier
Deal found 2/28![Frontier logo]()
$118
This Delta deal was found by Cheapflights users on 2/27. 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 5/1812:05 am
SFO
- MDW
1 stop6h 37m
Delta
Deal found 2/27![Delta logo]()
$119
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 February 28, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $177 (Southwest) |
One-way from | $89 (Southwest) |
Popular in | November |
Cheapest in | September |
Average price | $372 |
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 February 28, 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
OaklandChicago
OAK - MDW
OAKMDW
Oakland
Tue 5/5
5:45 am-3:05 pm
2 stops7h 20m
Chicago Midway
Fri 5/8
6:55 am-12:10 pm
1 stop7h 15m
$229
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Tue 4/21
10:55 pm-8:47 am
1 stop7h 52m
Chicago Midway
Sat 4/25
1:24 pm-7:03 pm
1 stop7h 39m
$237
OaklandChicago
OAK - MDW
OAKMDW
Oakland
Wed 3/25
11:55 pm-5:55 am
Nonstop4h 00m
Chicago Midway
Wed 4/1
9:00 pm-11:40 pm
Nonstop4h 40m
$247
OaklandChicago
OAK - MDW
OAKMDW
Oakland
Wed 3/11
5:50 am-11:55 am
Nonstop4h 05m
Chicago Midway
Thu 3/19
9:30 pm-12:10 am
Nonstop4h 40m
$272
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Wed 5/6
10:55 pm-8:43 am
1 stop7h 48m
Chicago Midway
Wed 5/13
12:51 pm-8:41 pm
1 stop9h 50m
$278
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Fri 4/24
5:15 am-11:25 am
Nonstop4h 10m
Chicago Midway
Mon 4/27
9:45 pm-12:20 am
Nonstop4h 35m
$285
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Tue 4/7
6:20 am-4:35 pm
2 stops8h 15m
Chicago Midway
Mon 4/13
4:10 pm-10:10 pm
2 stops8h 00m
$288
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Mon 5/18
11:25 pm-5:40 am
Nonstop4h 15m
Chicago Midway
Fri 5/22
9:45 pm-12:20 am
Nonstop4h 35m
$309
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Fri 5/8
8:45 pm-8:42 am
2 stops9h 57m
Chicago Midway
Mon 5/11
9:22 am-5:15 pm
2 stops9h 53m
$312
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Tue 4/7
10:55 pm-5:00 am
Nonstop4h 05m
Chicago Midway
Fri 4/10
5:25 am-10:20 am
1 stop6h 55m
$324
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.
SFO-MDW
OAK-MDW
SJC-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
SFO-MDW
OAK-MDW
SJC-MDW
What is the cheapest month to book a flight from San Francisco Bay Area to Chicago Midway Airport?
Currently, August is the cheapest month in which you can book a flight from San Francisco Bay Area to Chicago Midway Airport (average of $151). Flying from San Francisco Bay Area to Chicago Midway Airport in June is currently the most expensive (average of $240). 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 February 28, 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 38% 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 February 21, 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.
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 February 28, 2026.
See what other customers who have flown with Southwest, Delta, and United 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.
Boarding
8.1
Entertainment
7.5
Overall
8.0
Comfort
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Boarding
8.1
Entertainment
7.5
Overall
8.0
Comfort
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Boarding
8.1
Entertainment
7.5
Overall
8.0
Comfort
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Boarding
8.1
Entertainment
7.5
Overall
8.0
Comfort
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Boarding
8.1
Entertainment
7.5
Overall
8.0
Comfort
8.0
Crew
8.6
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 locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
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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 February 28, 2026.
San Francisco Bay Area and Midway flights
Browse other San Francisco Bay Area and Midway flight options. Last updated on February 28, 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 February 28, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$133 | Average$407 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$147 | Average$254 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$228 | Average$454 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$241 | Average$338 | FlexibilityNo cancel fee | On-timeN/A |