$132+ Cheap flights from Midway (MDW) to San Francisco (SFO)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/2. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SFO
May 22 — May 291
Round-trip
1 adult, Economy
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Find cheap flights from Midway to San Francisco with Cheapflights
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Cheapest flights from Midway to San FranciscoExplore the most affordable flight options available from Midway to San Francisco. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 22, 2026.
Explore the most affordable flight options available from Midway to San Francisco. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 22, 2026.
This Frontier deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/136:00 am
MDW
- SFO
1 stop15h 26m
Frontier
Mon 6/2210:10 pm
SFO
- MDW
1 stop11h 02m
Frontier
Deal found 4/20![Frontier logo]()
$244
This Trip.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/306:00 am
MDW
- SFO
1 stop13h 34m
Frontier
Mon 5/410:38 pm
SFO
- MDW
1 stop10h 31m
Frontier
Deal found 4/20![Frontier logo]()
$245
This Southwest deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/107:00 am
MDW
- SFO
1 stop8h 30m
Southwest
Wed 9/1611:40 pm
SFO
- MDW
Nonstop4h 10m
Southwest
Deal found 4/20![Southwest logo]()
$246
This Southwest deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 6/39:00 pm
MDW
- SFO
Nonstop4h 35m
Southwest
Sat 6/611:40 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Deal found 4/20![Southwest logo]()
$248
This Expedia deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2812:27 pm
MDW
- SFO
1 stop9h 07m
Frontier
Sun 5/3110:15 pm
SFO
- MDW
1 stop10h 54m
Frontier
Deal found 4/20![Frontier logo]()
$250
This Frontier deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/93:07 pm
MDW
- SFO
1 stop9h 57m
Frontier
Sun 5/1711:59 pm
SFO
- MDW
1 stop12h 13m
Frontier
Deal found 4/20![Frontier logo]()
$251
This Southwest deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” 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 5/96:15 am
MDW
- SFO
1 stop7h 25m
Southwest
Sat 5/1611:25 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Deal found 4/18![Southwest logo]()
$252
This Expedia deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia 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
Tue 5/510:15 pm
SFO
- MDW
1 stop10h 54m
Frontier
Deal found 4/17![Frontier logo]()
$255
This Travelocity deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/1412:19 pm
MDW
- SFO
1 stop9h 15m
Frontier
Sun 5/1711:59 pm
SFO
- MDW
1 stop12h 13m
Frontier
Deal found 4/19![Frontier logo]()
$256
This Trip.com deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/612:04 pm
MDW
- SFO
1 stop9h 30m
Frontier
Thu 5/711:59 pm
SFO
- MDW
1 stop12h 13m
Frontier
Deal found 4/17![Frontier logo]()
$257
This Delta deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 5/277:13 pm
MDW
- SFO
1 stop6h 37m
Delta
Sun 6/712:48 am
SFO
- MDW
1 stop5h 49m
Delta
Deal found 4/20![Delta logo]()
$258
Best flights from Midway to San FranciscoDiscover carefully curated flight deals from Midway to San Francisco that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 22, 2026.
Discover carefully curated flight deals from Midway to San Francisco that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 22, 2026.
This Southwest deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/314:55 pm
MDW
- SFO
1 stop8h 00m
Southwest
Sat 9/511:40 pm
SFO
- MDW
Nonstop4h 10m
Southwest
Deal found 4/21![Southwest logo]()
$269
This Southwest deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/206:45 am
MDW
- SFO
1 stop7h 50m
Southwest
Sat 5/2311:25 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Deal found 4/21![Southwest logo]()
$281
This Southwest deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/49:30 pm
MDW
- SFO
Nonstop4h 35m
Southwest
Wed 9/911:40 pm
SFO
- MDW
Nonstop4h 10m
Southwest
Deal found 4/20![Southwest logo]()
$283
This Southwest deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” 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 6/212:50 pm
MDW
- SFO
2 stops10h 35m
Southwest
Tue 6/95:10 am
SFO
- MDW
Nonstop4h 10m
Southwest
Deal found 4/18![Southwest logo]()
$298
This Southwest deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” 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 5/96:10 pm
MDW
- SFO
Nonstop4h 35m
Southwest
Mon 5/115:15 am
SFO
- MDW
Nonstop4h 10m
Southwest
Deal found 4/18![Southwest logo]()
$305
This Southwest deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” 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 5/96:10 am
MDW
- SFO
1 stop10h 15m
Southwest
Sat 5/165:40 am
SFO
- MDW
2 stops9h 35m
Southwest
Deal found 4/18![Southwest logo]()
$322
This Southwest deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 5/284:05 pm
MDW
- SFO
2 stops9h 00m
Southwest
Sat 6/65:10 am
SFO
- MDW
2 stops7h 35m
Southwest
Deal found 4/20![Southwest logo]()
$334
This Southwest deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 6/95:35 am
MDW
- SFO
1 stop8h 00m
Southwest
Sat 7/45:20 am
SFO
- MDW
2 stops7h 20m
Southwest
Deal found 4/19![Southwest logo]()
$343
This Southwest deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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 7/39:30 pm
MDW
- SFO
Nonstop4h 40m
Southwest
Tue 7/75:10 am
SFO
- MDW
Nonstop4h 10m
Southwest
Deal found 4/21![Southwest logo]()
$344
This Southwest deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 7/216:45 am
MDW
- SFO
1 stop6h 50m
Southwest
Mon 7/2711:40 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Deal found 4/19![Southwest logo]()
$345
This Southwest deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 6/15:30 am
MDW
- SFO
2 stops9h 05m
Southwest
Wed 6/310:30 am
SFO
- MDW
1 stop7h 25m
Southwest
Deal found 4/19![Southwest logo]()
$351
Last-minute flights from Midway to San FranciscoDiscover last-minute flight deals from Midway to San Francisco. Data last updated April 22, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to San Francisco. Data last updated April 22, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/296:10 am
MDW
- SFO
1 stop13h 24m
Frontier
Wed 5/611:59 pm
SFO
- MDW
1 stop12h 13m
Frontier
Deal found 4/20![Frontier logo]()
$263
This Trip.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/306:00 am
MDW
- SFO
1 stop13h 34m
Frontier
Mon 5/410:38 pm
SFO
- MDW
1 stop10h 31m
Frontier
Deal found 4/20![Frontier logo]()
$245
This Expedia deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia 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
Tue 5/510:15 pm
SFO
- MDW
1 stop10h 54m
Frontier
Deal found 4/17![Frontier logo]()
$255
This Trip.com deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/612:04 pm
MDW
- SFO
1 stop9h 30m
Frontier
Thu 5/711:59 pm
SFO
- MDW
1 stop12h 13m
Frontier
Deal found 4/17![Frontier logo]()
$257
This Super.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/712:19 pm
MDW
- SFO
1 stop9h 15m
Frontier
Mon 5/1110:15 pm
SFO
- MDW
1 stop10h 54m
Frontier
Deal found 4/20![Frontier logo]()
$260
This Frontier deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/93:07 pm
MDW
- SFO
1 stop9h 57m
Frontier
Sun 5/1711:59 pm
SFO
- MDW
1 stop12h 13m
Frontier
Deal found 4/20![Frontier logo]()
$251
This Southwest deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” 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 5/96:15 am
MDW
- SFO
1 stop7h 25m
Southwest
Sat 5/1611:25 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Deal found 4/18![Southwest logo]()
$252
This Vliegwinkel deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/93:07 pm
MDW
- SFO
1 stop9h 57m
Frontier
Sat 5/1610:15 pm
SFO
- MDW
1 stop10h 54m
Frontier
Deal found 4/18![Frontier logo]()
$265
This Travelocity deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/1412:19 pm
MDW
- SFO
1 stop9h 15m
Frontier
Sun 5/1711:59 pm
SFO
- MDW
1 stop12h 13m
Frontier
Deal found 4/19![Frontier logo]()
$256
This Delta deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 5/277:13 pm
MDW
- SFO
1 stop6h 37m
Delta
Sun 6/712:48 am
SFO
- MDW
1 stop5h 49m
Delta
Deal found 4/20![Delta logo]()
$258
This Expedia deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2812:27 pm
MDW
- SFO
1 stop9h 07m
Frontier
Sun 5/3110:15 pm
SFO
- MDW
1 stop10h 54m
Frontier
Deal found 4/20![Frontier logo]()
$250
One-way flights from Midway to San FranciscoSearch for one-way flight options from Midway to San Francisco. Find affordable one-way fares based on user searches. Data last updated April 22, 2026.
Search for one-way flight options from Midway to San Francisco. Find affordable one-way fares based on user searches. Data last updated April 22, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 6/23:07 pm
MDW
- SFO
2 stops21h 34m
Frontier
Deal found 4/19![Frontier logo]()
$132
This Trip.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/306:00 am
MDW
- SFO
1 stop13h 34m
Frontier
Deal found 4/20![Frontier logo]()
$133
This Trip.com deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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.
Wed 4/296:10 am
MDW
- SFO
1 stop13h 24m
Frontier
Deal found 4/21![Frontier logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/317:49 pm
MDW
- SFO
2 stops23h 18m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/53:07 pm
MDW
- SFO
2 stops35h 16m
Frontier
Deal found 4/17![Frontier logo]()
$139
This Southwest deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 8/154:05 pm
MDW
- SFO
1 stop6h 30m
Southwest
Deal found 4/20![Southwest logo]()
$140
This Southwest deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 6/29:00 pm
MDW
- SFO
Nonstop4h 35m
Southwest
Deal found 4/19![Southwest logo]()
$142
This Super.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1611:59 am
MDW
- SFO
1 stop9h 35m
Frontier
Deal found 4/20![Frontier logo]()
$143
This Priceline deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/2312:27 pm
MDW
- SFO
1 stop8h 59m
Frontier
Deal found 4/17![Frontier logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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.
Fri 5/153:07 pm
MDW
- SFO
2 stops28h 55m
Frontier
Deal found 4/20![Frontier logo]()
$146
Find flight deals from Midway to San Francisco
Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to San Francisco (SFO). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated April 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $244 (Frontier) |
One-way from | $132 (Kiwi.com) |
Popular in | February |
Cheapest in | October |
Average price | $312 |
Good round-trip deal | $353 or less |
Good one-way deal | $240 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to San Francisco that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 22, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to San Francisco that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Mon 8/31
4:55 pm-10:55 pm
1 stop8h 00m
San Francisco
Sat 9/5
11:40 pm-5:50 am
Nonstop4h 10m
$269
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Wed 5/20
6:45 am-12:35 pm
1 stop7h 50m
San Francisco
Sat 5/23
11:25 pm-5:40 am
Nonstop4h 15m
$281
Quickest round-trip
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Fri 9/4
9:30 pm-12:05 am
Nonstop4h 35m
San Francisco
Wed 9/9
11:40 pm-5:50 am
Nonstop4h 10m
$283
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Tue 6/2
12:50 pm-9:25 pm
2 stops10h 35m
San Francisco
Tue 6/9
5:10 am-11:20 am
Nonstop4h 10m
$298
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Sat 5/9
6:10 pm-8:45 pm
Nonstop4h 35m
San Francisco
Mon 5/11
5:15 am-11:25 am
Nonstop4h 10m
$305
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Sat 5/9
6:10 am-2:25 pm
1 stop10h 15m
San Francisco
Sat 5/16
5:40 am-5:15 pm
2 stops9h 35m
$322
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Thu 5/28
4:05 pm-11:05 pm
2 stops9h 00m
San Francisco
Sat 6/6
5:10 am-2:45 pm
2 stops7h 35m
$334
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Tue 6/9
5:35 am-11:35 am
1 stop8h 00m
San Francisco
Sat 7/4
5:20 am-2:40 pm
2 stops7h 20m
$343
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Fri 7/3
9:30 pm-12:10 am
Nonstop4h 40m
San Francisco
Tue 7/7
5:10 am-11:20 am
Nonstop4h 10m
$344
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Tue 7/21
6:45 am-11:35 am
1 stop6h 50m
San Francisco
Mon 7/27
11:40 pm-5:55 am
Nonstop4h 15m
$345
Showing 1-10 of 23 resultsSorted by cheapest first
Compare providers for flights from Midway to San Francisco
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to San Francisco in April.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago Midway Airport-San Francisco flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-San Francisco flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-San Francisco flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago Midway Airport-San Francisco flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-San Francisco flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Midway to San Francisco
Have a flexible travel schedule? Discover the best time to fly to San Francisco from Midway with our price prediction graph.
MDW-SFO
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago Midway Airport to San Francisco
Prices
Delays
What is the cheapest month to book a flight from Chicago Midway Airport to San Francisco?
Currently, October is the cheapest month in which you can book a flight from Chicago Midway Airport to San Francisco (average of $297). Flying from Chicago Midway Airport to San Francisco in February is currently the most expensive (average of $635). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from MDW to SFO?
Find hourly flight availability from Midway to San Francisco. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 22, 2026.
It’s typically best to fly out from Chicago Midway Airport to San Francisco in the evening. Doing so could potentially save you 24% on the flight price compared to flying at noon, which is usually more expensive.
What is the cheapest day to fly from Chicago Midway Airport to San Francisco?
Use this chart to determine the cheapest time to fly round-trip from Midway to San Francisco. Price data was last updated on April 18, 2026.
Travelers seeking maximum savings on their Chicago Midway Airport to San Francisco flight should consider departing on Tuesday afternoons when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
How often are flights from Chicago to San Francisco delayed?
About 26% of weekly flights between Chicago and San Francisco have experienced delays in the past year, with the average delay time being 136 minutes.
What is the most punctual flight time for Chicago to San Francisco flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving at night tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Thursday tends to have the lowest number of delays on this route, whereas Monday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to San Francisco flights?
Over the last year, Southwest have had the lowest number of delays on this route, with just 25% of flights being delayed.
Reviews of airlines servicing San Francisco
Get insights into the airlines that provide service to San Francisco. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to San Francisco. Reviews last updated April 22, 2026.
Read reviews from past customers who have flown Southwest from Chicago Midway Airport to San Francisco. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from Midway to San Francisco. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near San Francisco?
Book flights to San Francisco if you plan to visit one of these locationsSouth San Francisco
Santa Cruz
Santa Clara
Rancho Cordova
San Bruno
Watsonville
San Ramon
Union City
Emeryville
Newark
Vacaville
Roseville
San Carlos
Redwood City
Sunnyvale
Turlock
San Lorenzo
Davis
Manteca
Elk Grove
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Midway and San Francisco flights
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Top airline flying from Midway to San Francisco
Discover the top airline that operate flights from Midway to San Francisco. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$231 | Average$411 | FlexibilityNo cancel fee | On-time63% |