$89+ 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 5/7. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SFO
Apr 2 — Apr 91
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Midway to San Francisco Bay Area with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Midway to San Francisco Bay Area
Cheapest
Best
Last-minute
One-way
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 March 3, 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 March 3, 2026.
This Southwest deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 4/2510:00 am
MDW
- SFO
Nonstop4h 35m
Southwest
Wed 4/295:25 am
SFO
- MDW
Nonstop4h 10m
Southwest
Deal found 3/1![Southwest logo]()
$224
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.
Tue 4/142:15 pm
MDW
- SFO
1 stop29h 19m
Frontier
Thu 4/169:58 am
SFO
- MDW
2 stops26h 36m
Frontier
Deal found 2/27![Frontier logo]()
$225
This Kiwi.com deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 4/156:30 am
MDW
- SFO
1 stop13h 04m
Frontier
Sat 4/186:00 am
SFO
- MDW
2 stops14h 14m
Frontier
Deal found 3/1![Frontier logo]()
$226
This Southwest deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/185:10 am
MDW
- SFO
1 stop8h 40m
Southwest
Sat 4/255:40 am
SFO
- MDW
2 stops9h 35m
Southwest
Deal found 3/1![Southwest logo]()
$227
This Kiwi.com deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 4/156:30 am
MDW
- SFO
1 stop13h 04m
Frontier
Wed 4/227:00 am
SFO
- MDW
2 stops13h 14m
Frontier
Deal found 3/1![Frontier logo]()
$228
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 4/89:00 pm
MDW
- SFO
Nonstop4h 35m
Southwest
Tue 4/145:25 am
SFO
- MDW
Nonstop4h 10m
Southwest
Deal found 2/26![Southwest logo]()
$230
This Trip.com deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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.
Sat 4/186:00 am
MDW
- SFO
1 stop13h 34m
Frontier
Sun 4/2611:16 pm
SFO
- MDW
1 stop11h 19m
Frontier
Deal found 3/2![Frontier logo]()
$231
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 4/83:00 pm
MDW
- SFO
1 stop7h 55m
Southwest
Wed 4/155:25 am
SFO
- MDW
Nonstop4h 10m
Southwest
Deal found 2/26![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 4/257:50 am
MDW
- SFO
2 stops9h 35m
Southwest
Sat 5/25:40 am
SFO
- MDW
2 stops9h 35m
Southwest
Deal found 2/28![Southwest logo]()
$233
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.
Thu 4/308:25 am
MDW
- SFO
1 stop16h 06m
Frontier
Sun 5/36:00 am
SFO
- MDW
2 stops14h 15m
Frontier
Deal found 2/27![Frontier logo]()
$235
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.
Sat 5/26:00 am
MDW
- SFO
1 stop13h 34m
Frontier
Sat 5/27:40 pm
SFO
- MDW
2 stops24h 35m
Frontier
Deal found 2/27![Frontier logo]()
$236
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.
Fri 5/19:50 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Sun 5/35:10 pm
OAK
- MDW
1 stop6h 45m
Southwest
Deal found 2/26![Southwest logo]()
$241
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 March 3, 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 March 3, 2026.
This Southwest deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 4/166:40 am
MDW
- SFO
1 stop6h 55m
Southwest
Sat 4/1811:25 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Deal found 3/1![Southwest logo]()
$254
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 4/241:24 pm
MDW
- SFO
1 stop7h 39m
Delta
Mon 4/279:35 pm
SFO
- MDW
1 stop10h 21m
Delta
Deal found 2/27![Delta logo]()
$265
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.
Mon 5/47:16 pm
MDW
- SFO
1 stop6h 38m
Delta
Mon 5/116:00 am
SFO
- MDW
1 stop8h 12m
Delta
Deal found 2/28![Delta logo]()
$265
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.
Fri 4/310:10 am
MDW
- SFO
1 stop9h 45m
Southwest
Tue 4/711:25 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Deal found 2/26![Southwest logo]()
$267
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 5/139:00 pm
MDW
- SFO
Nonstop4h 35m
Southwest
Fri 5/1511:25 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Deal found 2/26![Southwest logo]()
$267
This Southwest deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 4/154:00 pm
MDW
- SFO
2 stops9h 15m
Southwest
Fri 4/175:15 am
SFO
- MDW
Nonstop4h 10m
Southwest
Deal found 3/1![Southwest logo]()
$280
This Delta deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 4/291:24 pm
MDW
- SFO
1 stop7h 39m
Delta
Sun 5/310:55 pm
SFO
- MDW
1 stop7h 52m
Delta
Deal found 3/1![Delta logo]()
$318
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.
Thu 5/77:30 am
MDW
- SFO
1 stop9h 30m
Southwest
Sun 5/105:20 am
SFO
- MDW
Nonstop4h 10m
Southwest
Deal found 2/26![Southwest logo]()
$282
This Southwest deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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 4/109:50 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Sun 4/1211:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Deal found 3/3![Southwest logo]()
$285
This Southwest deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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 4/36:05 am
MDW
- SFO
1 stop7h 35m
Southwest
Thu 4/95:15 am
SFO
- MDW
Nonstop4h 10m
Southwest
Deal found 3/3![Southwest logo]()
$295
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.
Wed 8/1210:35 am
MDW
- SJC
1 stop10h 02m
Delta
Mon 8/1710:20 pm
SJC
- MDW
1 stop9h 30m
Delta
Deal found 2/28![Delta logo]()
$407
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.
Wed 4/156:05 pm
MDW
- SFO
1 stop7h 10m
Southwest
Sun 4/195:20 am
SFO
- MDW
Nonstop4h 10m
Southwest
Deal found 2/27![Southwest logo]()
$295
This Southwest deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 4/179:50 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Mon 4/201:25 pm
OAK
- MDW
1 stop7h 15m
Southwest
Deal found 3/1![Southwest logo]()
$295
This Southwest deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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 5/157:40 pm
MDW
- OAK
1 stop6h 25m
Southwest
Mon 5/1811:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Deal found 3/2![Southwest logo]()
$295
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.
Tue 7/78:00 am
MDW
- SFO
1 stop9h 00m
Southwest
Sat 7/1111:40 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Deal found 2/28![Southwest logo]()
$306
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.
Mon 3/306:35 pm
MDW
- SFO
2 stops7h 35m
Southwest
Wed 4/15:55 am
SFO
- MDW
2 stops8h 15m
Southwest
Deal found 2/27![Southwest logo]()
$315
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.
Fri 4/39:30 pm
MDW
- OAK
Nonstop4h 40m
Southwest
Mon 4/68:00 pm
OAK
- MDW
1 stop7h 40m
Southwest
Deal found 2/26![Southwest logo]()
$317
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 4/268:35 am
MDW
- OAK
1 stop7h 05m
Southwest
Sat 5/27:50 pm
OAK
- MDW
1 stop7h 10m
Southwest
Deal found 2/28![Southwest logo]()
$322
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.
Sat 4/45:40 pm
MDW
- SJC
2 stops7h 50m
Southwest
Tue 4/79:10 pm
SJC
- MDW
1 stop5h 50m
Southwest
Deal found 2/26![Southwest logo]()
$337
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 6/226:00 pm
MDW
- OAK
1 stop6h 25m
Southwest
Mon 6/2911:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Deal found 2/26![Southwest logo]()
$343
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.
Fri 7/318:50 pm
MDW
- SJC
Nonstop4h 35m
Southwest
Sun 8/210:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Deal found 2/26![Southwest logo]()
$387
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 6/310:20 am
MDW
- SJC
Nonstop4h 35m
Southwest
Mon 6/84:20 pm
SJC
- MDW
1 stop5h 55m
Southwest
Deal found 2/28![Southwest logo]()
$393
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.
Sat 8/82:05 pm
MDW
- SJC
1 stop7h 20m
Southwest
Sun 8/166:10 am
SJC
- MDW
Nonstop4h 10m
Southwest
Deal found 2/27![Southwest logo]()
$397
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.
Thu 7/165:45 am
MDW
- SJC
1 stop6h 40m
Southwest
Mon 7/204:20 pm
SJC
- MDW
1 stop5h 55m
Southwest
Deal found 2/28![Southwest logo]()
$402
This Southwest deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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 6/248:55 pm
MDW
- SJC
Nonstop4h 30m
Southwest
Wed 7/110:55 pm
SJC
- MDW
Nonstop4h 05m
Southwest
Deal found 3/2![Southwest logo]()
$407
This Southwest deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 3/2610:00 am
MDW
- SJC
1 stop6h 10m
Southwest
Thu 4/28:40 pm
SJC
- MDW
1 stop7h 05m
Southwest
Deal found 3/1![Southwest logo]()
$411
This Southwest deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 6/245:50 pm
MDW
- SJC
2 stops7h 10m
Southwest
Sun 6/289:55 pm
SJC
- MDW
1 stop5h 45m
Southwest
Deal found 3/1![Southwest logo]()
$412
This Southwest deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/305:35 am
MDW
- OAK
1 stop6h 15m
Southwest
Mon 7/62:15 pm
OAK
- MDW
1 stop7h 10m
Southwest
Deal found 3/1![Southwest logo]()
$414
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 3/1811:50 am
MDW
- OAK
2 stops8h 40m
Southwest
Wed 3/259:15 pm
OAK
- MDW
1 stop6h 30m
Southwest
Deal found 2/28![Southwest logo]()
$416
This Southwest deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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 5/225:25 pm
MDW
- OAK
1 stop7h 05m
Southwest
Mon 6/88:30 pm
OAK
- MDW
1 stop6h 10m
Southwest
Deal found 3/2![Southwest logo]()
$427
Last-minute flights from Midway to San Francisco Bay AreaDiscover last-minute flight deals from Midway to San Francisco Bay Area. Data last updated March 3, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to San Francisco Bay Area. Data last updated March 3, 2026 and is based on user searches.
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 4/89:00 pm
MDW
- SFO
Nonstop4h 35m
Southwest
Tue 4/145:25 am
SFO
- MDW
Nonstop4h 10m
Southwest
Deal found 2/26![Southwest logo]()
$230
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 4/83:00 pm
MDW
- SFO
1 stop7h 55m
Southwest
Wed 4/155:25 am
SFO
- MDW
Nonstop4h 10m
Southwest
Deal found 2/26![Southwest logo]()
$232
This Delta deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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 4/87:20 pm
MDW
- SFO
1 stop6h 42m
Delta
Tue 4/1410:30 pm
SFO
- MDW
1 stop9h 26m
Delta
Deal found 3/2![Delta logo]()
$237
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.
Tue 4/142:15 pm
MDW
- SFO
1 stop29h 19m
Frontier
Thu 4/169:58 am
SFO
- MDW
2 stops26h 36m
Frontier
Deal found 2/27![Frontier logo]()
$225
This Southwest deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 4/148:50 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Tue 4/2111:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Deal found 3/1![Southwest logo]()
$245
This Kiwi.com deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 4/156:30 am
MDW
- SFO
1 stop13h 04m
Frontier
Sat 4/186:00 am
SFO
- MDW
2 stops14h 14m
Frontier
Deal found 3/1![Frontier logo]()
$226
This Kiwi.com deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 4/156:30 am
MDW
- SFO
1 stop13h 04m
Frontier
Wed 4/227:00 am
SFO
- MDW
2 stops13h 14m
Frontier
Deal found 3/1![Frontier logo]()
$228
This Southwest deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/185:10 am
MDW
- SFO
1 stop8h 40m
Southwest
Sat 4/255:40 am
SFO
- MDW
2 stops9h 35m
Southwest
Deal found 3/1![Southwest logo]()
$227
This Trip.com deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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.
Sat 4/186:00 am
MDW
- SFO
1 stop13h 34m
Frontier
Sun 4/2611:16 pm
SFO
- MDW
1 stop11h 19m
Frontier
Deal found 3/2![Frontier logo]()
$231
This Southwest deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 4/2510:00 am
MDW
- SFO
Nonstop4h 35m
Southwest
Wed 4/295:25 am
SFO
- MDW
Nonstop4h 10m
Southwest
Deal found 3/1![Southwest logo]()
$224
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 4/257:50 am
MDW
- SFO
2 stops9h 35m
Southwest
Sat 5/25:40 am
SFO
- MDW
2 stops9h 35m
Southwest
Deal found 2/28![Southwest logo]()
$233
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.
Thu 4/308:25 am
MDW
- SFO
1 stop16h 06m
Frontier
Sun 5/36:00 am
SFO
- MDW
2 stops14h 15m
Frontier
Deal found 2/27![Frontier logo]()
$235
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 March 3, 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 March 3, 2026.
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 5/79:50 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Deal found 2/27![Southwest logo]()
$89
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.
Sun 5/36:20 am
MDW
- SFO
2 stops37h 08m
Frontier
Deal found 2/26![Frontier logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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 4/204:14 pm
MDW
- SFO
2 stops33h 11m
Frontier
Deal found 3/3![Frontier logo]()
$114
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 4/79:00 pm
MDW
- SFO
Nonstop4h 35m
Southwest
Deal found 2/26![Southwest logo]()
$115
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/184:09 pm
MDW
- SFO
1 stop8h 22m
Frontier
Deal found 2/28![Frontier logo]()
$116
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.
Tue 4/142:15 pm
MDW
- SFO
2 stops35h 10m
Frontier
Deal found 2/26![Frontier logo]()
$117
This Delta deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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 4/11:10 pm
MDW
- SFO
1 stop7h 57m
Delta
Deal found 3/2![Delta logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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 5/96:00 am
MDW
- SFO
2 stops29h 08m
Frontier
Deal found 3/3![Frontier logo]()
$120
This Kiwi.com deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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 3/303:20 pm
MDW
- SFO
2 stops29h 17m
Frontier
Deal found 3/2![Frontier logo]()
$121
This Southwest deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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 4/149:00 pm
MDW
- SFO
Nonstop4h 35m
Southwest
Deal found 3/2![Southwest logo]()
$123
This Southwest deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/49:40 pm
MDW
- OAK
Nonstop4h 40m
Southwest
Deal found 3/2![Southwest logo]()
$123
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.
Tue 8/259:11 pm
MDW
- SFO
2 stops23h 14m
Frontier
Deal found 2/26![Frontier logo]()
$124
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 March 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $224 (Southwest) |
One-way from | $89 (Southwest) |
Popular in | December |
Cheapest in | April |
Average price | $364 |
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 March 3, 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
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Thu 4/16
6:40 am-11:35 am
1 stop6h 55m
San Francisco
Sat 4/18
11:25 pm-5:40 am
Nonstop4h 15m
$254
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Fri 4/24
1:24 pm-7:03 pm
1 stop7h 39m
San Francisco
Mon 4/27
9:35 pm-9:56 am
1 stop10h 21m
$265
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Mon 5/4
7:16 pm-11:54 pm
1 stop6h 38m
San Francisco
Mon 5/11
6:00 am-4:12 pm
1 stop8h 12m
$265
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Fri 4/3
10:10 am-5:55 pm
1 stop9h 45m
San Francisco
Tue 4/7
11:25 pm-5:40 am
Nonstop4h 15m
$267
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Wed 5/13
9:00 pm-11:35 pm
Nonstop4h 35m
San Francisco
Fri 5/15
11:25 pm-5:40 am
Nonstop4h 15m
$267
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Wed 4/15
4:00 pm-11:15 pm
2 stops9h 15m
San Francisco
Fri 4/17
5:15 am-11:25 am
Nonstop4h 10m
$280
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Thu 5/7
7:30 am-3:00 pm
1 stop9h 30m
San Francisco
Sun 5/10
5:20 am-11:30 am
Nonstop4h 10m
$282
ChicagoOakland
MDW - OAK
MDWOAK
Chicago Midway
Fri 4/10
9:50 pm-12:25 am
Nonstop4h 35m
Oakland
Sun 4/12
11:55 pm-6:00 am
Nonstop4h 05m
$285
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Fri 4/3
6:05 am-11:40 am
1 stop7h 35m
San Francisco
Thu 4/9
5:15 am-11:25 am
Nonstop4h 10m
$295
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Wed 4/15
6:05 pm-11:15 pm
1 stop7h 10m
San Francisco
Sun 4/19
5:20 am-11:30 am
Nonstop4h 10m
$295
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 $145). Flying from Chicago Midway Airport to San Francisco Bay Area in November is currently the most expensive (average of $332). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from MDW to 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 March 3, 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 evening.
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 February 21, 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. Sunday 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 March 3, 2026.
Read reviews from past customers who have flown Southwest, United Airlines, and Frontier 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.
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentWalter,Aug 2025
OAK - SAN
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentWalter,Aug 2025
OAK - SAN
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentWalter,Aug 2025
OAK - SAN
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentWalter,Aug 2025
OAK - SAN
Related info for your journey
Find useful and relevant information for your journey from Midway to San Francisco Bay Area. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Alternative routes for Midway to San Francisco Bay Area
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to San Francisco Bay Area by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Midway to San Francisco Bay Area by cabin class
Find flights from Midway to San Francisco Bay Area, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Midway and San Francisco Bay Area flights
Browse other Midway and San Francisco Bay Area flight options. Last updated on March 3, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 3 airlines flying from Midway to San Francisco Bay Area
Discover the top 3 airlines 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 March 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$90 | Average$217 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$217 | Average$418 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$217 | Average$430 | FlexibilityNo cancel fee | On-time63% |