$136+ Cheap flights from San Francisco (SFO) 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 7/27. Fares are subject to change and may not be available on all flights or dates of travel.
SFO — MDW
Jun 25 — Jul 21
Round-trip
1 adult, Economy
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Find cheap flights from San Francisco to Midway 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.Cheapflights Tip: The best prices from San Francisco to Chicago Midway are usually found in January or August, booked 84 days in advance, depart on a Wednesday or Tuesday and return on a Wednesday
Cheap flight deals from San Francisco to Midway
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Best
Last-minute
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Cheapest flights from San Francisco to MidwayExplore the most affordable flight options available from San Francisco to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 26, 2026.
Explore the most affordable flight options available from San Francisco to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 26, 2026.
This Southwest deal was found by Cheapflights users on 5/21. 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 7/135:50 am
SFO
- MDW
Nonstop4h 10m
Southwest
Tue 7/216:00 am
MDW
- SFO
1 stop9h 40m
Southwest
Deal found 5/21![Southwest logo]()
$306
This Delta deal was found by Cheapflights users on 5/25. 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 9/2312:30 am
SFO
- MDW
1 stop6h 20m
Delta
Mon 9/281:00 pm
MDW
- SFO
1 stop10h 53m
Delta
Deal found 5/25![Delta logo]()
$307
This Southwest deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” 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 7/75:00 am
SFO
- MDW
2 stops7h 35m
Southwest
Wed 7/229:30 pm
MDW
- SFO
Nonstop4h 45m
Southwest
Deal found 5/22![Southwest logo]()
$309
This Southwest deal was found by Cheapflights users on 5/25. 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.
Sat 8/15:55 pm
SFO
- MDW
1 stop9h 30m
Southwest
Wed 8/57:35 pm
MDW
- SFO
Nonstop4h 30m
Southwest
Deal found 5/25![Southwest logo]()
$310
This Southwest deal was found by Cheapflights users on 5/25. 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 8/2811:40 pm
SFO
- MDW
Nonstop4h 10m
Southwest
Mon 8/319:30 pm
MDW
- SFO
Nonstop4h 35m
Southwest
Deal found 5/25![Southwest logo]()
$311
This Southwest deal was found by Cheapflights users on 5/26. 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 7/285:15 am
SFO
- MDW
Nonstop4h 10m
Southwest
Tue 7/289:30 pm
MDW
- SFO
Nonstop4h 45m
Southwest
Deal found 5/26![Southwest logo]()
$312
This Southwest deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” 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 7/3012:50 pm
SFO
- MDW
1 stop8h 55m
Southwest
Tue 8/47:35 pm
MDW
- SFO
Nonstop4h 30m
Southwest
Deal found 5/23![Southwest logo]()
$313
This Delta deal was found by Cheapflights users on 5/25. 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.
Mon 7/612:35 am
SFO
- MDW
1 stop6h 02m
Delta
Thu 7/97:06 pm
MDW
- SFO
1 stop6h 40m
Delta
Deal found 5/25![Delta logo]()
$314
This Southwest deal was found by Cheapflights users on 5/21. 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.
Tue 7/75:15 am
SFO
- MDW
Nonstop4h 10m
Southwest
Fri 7/108:15 pm
MDW
- SFO
1 stop6h 15m
Southwest
Deal found 5/21![Southwest logo]()
$315
This Southwest deal was found by Cheapflights users on 5/21. 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.
Tue 6/163:35 pm
SFO
- MDW
1 stop6h 30m
Southwest
Wed 6/176:00 am
MDW
- SFO
1 stop9h 40m
Southwest
Deal found 5/21![Southwest logo]()
$316
This Frontier deal was found by Cheapflights users on 5/24. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/2610:10 pm
SFO
- MDW
1 stop10h 54m
Frontier
Thu 7/26:00 am
MDW
- SFO
1 stop15h 26m
Frontier
Deal found 5/24![Frontier logo]()
$317
This Trip.com deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” 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 6/1912:32 am
SFO
- MDW
1 stop12h 43m
Frontier
Fri 7/312:04 pm
MDW
- SFO
1 stop9h 22m
Frontier
Deal found 5/22![Frontier logo]()
$318
Best flights from San Francisco to MidwayDiscover carefully curated flight deals from San Francisco to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 26, 2026.
Discover carefully curated flight deals from San Francisco to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 26, 2026.
This Southwest deal was found by Cheapflights users on 5/25. 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 8/2111:40 pm
SFO
- MDW
Nonstop4h 10m
Southwest
Tue 8/259:05 am
MDW
- SFO
1 stop9h 20m
Southwest
Deal found 5/25![Southwest logo]()
$313
This Delta deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/226:00 am
SFO
- MDW
1 stop8h 27m
Delta
Fri 9/256:45 pm
MDW
- SFO
1 stop7h 00m
Delta
Deal found 5/22![Delta logo]()
$364
This Southwest deal was found by Cheapflights users on 5/21. 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 7/812:15 pm
SFO
- MDW
1 stop9h 05m
Southwest
Mon 7/135:10 am
MDW
- SFO
1 stop8h 10m
Southwest
Deal found 5/21![Southwest logo]()
$316
This Southwest deal was found by Cheapflights users on 5/25. 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 7/62:15 pm
SFO
- MDW
2 stops8h 00m
Southwest
Tue 7/145:30 am
MDW
- SFO
1 stop6h 20m
Southwest
Deal found 5/25![Southwest logo]()
$337
This Southwest deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” 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 9/105:35 am
SFO
- MDW
Nonstop4h 05m
Southwest
Sun 9/139:20 pm
MDW
- SFO
Nonstop4h 35m
Southwest
Deal found 5/23![Southwest logo]()
$347
This Southwest deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” 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 8/811:40 pm
SFO
- MDW
Nonstop4h 10m
Southwest
Sat 8/156:00 pm
MDW
- SFO
Nonstop4h 35m
Southwest
Deal found 5/23![Southwest logo]()
$353
This Southwest deal was found by Cheapflights users on 5/25. 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 9/412:40 pm
SFO
- MDW
1 stop8h 40m
Southwest
Mon 9/75:30 am
MDW
- SFO
1 stop8h 05m
Southwest
Deal found 5/25![Southwest logo]()
$364
This Southwest deal was found by Cheapflights users on 5/21. 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.
Sat 7/45:00 am
SFO
- MDW
2 stops7h 35m
Southwest
Tue 7/75:35 am
MDW
- SFO
1 stop8h 00m
Southwest
Deal found 5/21![Southwest logo]()
$369
This Southwest deal was found by Cheapflights users on 5/21. 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 11/135:40 am
SFO
- MDW
Nonstop4h 05m
Southwest
Fri 11/206:30 am
MDW
- SFO
1 stop7h 55m
Southwest
Deal found 5/21![Southwest logo]()
$372
This Southwest deal was found by Cheapflights users on 5/24. 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 8/275:35 am
SFO
- MDW
Nonstop4h 05m
Southwest
Sun 8/308:30 pm
MDW
- SFO
Nonstop4h 35m
Southwest
Deal found 5/24![Southwest logo]()
$380
Last-minute flights from San Francisco to MidwayDiscover last-minute flight deals from San Francisco to Midway. Data last updated May 26, 2026 and is based on user searches.
Discover last-minute flight deals from San Francisco to Midway. Data last updated May 26, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 5/25. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/2611:59 pm
SFO
- MDW
1 stop12h 13m
Frontier
Tue 6/23:07 pm
MDW
- SFO
1 stop9h 57m
Frontier
Deal found 5/25![Frontier logo]()
$324
This Trip.com deal was found by Cheapflights users on 5/25. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/210:10 pm
SFO
- MDW
1 stop10h 59m
Frontier
Sat 6/611:59 am
MDW
- SFO
1 stop9h 58m
Frontier
Deal found 5/25![Frontier logo]()
$333
This Frontier deal was found by Cheapflights users on 5/24. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/1212:32 am
SFO
- MDW
1 stop12h 43m
Frontier
Sat 6/274:10 pm
MDW
- SFO
1 stop8h 52m
Frontier
Deal found 5/24![Frontier logo]()
$323
This Southwest deal was found by Cheapflights users on 5/21. 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.
Tue 6/163:35 pm
SFO
- MDW
1 stop6h 30m
Southwest
Wed 6/176:00 am
MDW
- SFO
1 stop9h 40m
Southwest
Deal found 5/21![Southwest logo]()
$316
This Frontier deal was found by Cheapflights users on 5/25. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/1812:32 am
SFO
- MDW
1 stop12h 43m
Frontier
Sat 6/2011:59 am
MDW
- SFO
1 stop9h 56m
Frontier
Deal found 5/25![Frontier logo]()
$322
This Trip.com deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” 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 6/1912:32 am
SFO
- MDW
1 stop12h 43m
Frontier
Fri 7/312:04 pm
MDW
- SFO
1 stop9h 22m
Frontier
Deal found 5/22![Frontier logo]()
$318
This Southwest deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” 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 6/227:45 pm
SFO
- MDW
1 stop6h 55m
Southwest
Wed 7/15:30 am
MDW
- SFO
1 stop6h 20m
Southwest
Deal found 5/23![Southwest logo]()
$314
This Southwest deal was found by Cheapflights users on 5/21. 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 6/246:00 am
SFO
- MDW
2 stops8h 55m
Southwest
Wed 7/15:30 am
MDW
- SFO
1 stop6h 20m
Southwest
Deal found 5/21![Southwest logo]()
$330
This Frontier deal was found by Cheapflights users on 5/24. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/2610:10 pm
SFO
- MDW
1 stop10h 54m
Frontier
Thu 7/26:00 am
MDW
- SFO
1 stop15h 26m
Frontier
Deal found 5/24![Frontier logo]()
$317
This CheapOair deal was found by Cheapflights users on 5/25. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/2612:32 am
SFO
- MDW
1 stop12h 43m
Frontier
Thu 7/26:00 am
MDW
- SFO
1 stop15h 26m
Frontier
Deal found 5/25![Frontier logo]()
$327
This Frontier deal was found by Cheapflights users on 5/25. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/2712:32 am
SFO
- MDW
1 stop12h 43m
Frontier
Thu 7/26:00 am
MDW
- SFO
1 stop15h 26m
Frontier
Deal found 5/25![Frontier logo]()
$319
This Frontier deal was found by Cheapflights users on 5/25. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/2712:32 am
SFO
- MDW
1 stop12h 43m
Frontier
Fri 7/34:10 pm
MDW
- SFO
1 stop8h 52m
Frontier
Deal found 5/25![Frontier logo]()
$329
One-way flights from San Francisco to MidwaySearch for one-way flight options from San Francisco to Midway. Find affordable one-way fares based on user searches. Data last updated May 26, 2026.
Search for one-way flight options from San Francisco to Midway. Find affordable one-way fares based on user searches. Data last updated May 26, 2026.
This Frontier deal was found by Cheapflights users on 5/25. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/2711:00 pm
SFO
- MDW
1 stop10h 07m
Frontier
Deal found 5/25![Frontier logo]()
$136
This Delta deal was found by Cheapflights users on 5/25. 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 8/1910:59 pm
SFO
- MDW
1 stop8h 18m
Delta
Deal found 5/25![Delta logo]()
$137
This Delta deal was found by Cheapflights users on 5/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/710:59 pm
SFO
- MDW
1 stop9h 06m
Delta
Deal found 5/21![Delta logo]()
$139
This Super.com deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” 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.
Fri 6/2612:32 am
SFO
- MDW
1 stop12h 43m
Frontier
Deal found 5/23![Frontier logo]()
$140
This Southwest deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:00 am
SFO
- MDW
2 stops9h 10m
Southwest
Deal found 5/22![Southwest logo]()
$142
This Super.com deal was found by Cheapflights users on 5/24. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/210:10 pm
SFO
- MDW
1 stop10h 57m
Frontier
Deal found 5/24![Frontier logo]()
$143
This Southwest deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” 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 9/2611:40 pm
SFO
- MDW
Nonstop4h 10m
Southwest
Deal found 5/22![Southwest logo]()
$144
This Delta deal was found by Cheapflights users on 5/25. 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.
Thu 8/2010:59 pm
SFO
- MDW
1 stop8h 18m
Delta
Deal found 5/25![Delta logo]()
$145
This Trip.com deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” 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 8/2111:52 pm
SFO
- MDW
1 stop12h 15m
Frontier
Deal found 5/23![Frontier logo]()
$147
This Southwest deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/166:35 am
SFO
- MDW
2 stops7h 25m
Southwest
Deal found 5/22![Southwest logo]()
$150
This Delta deal was found by Cheapflights users on 5/25. 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.
Fri 9/2512:30 am
SFO
- MDW
1 stop6h 20m
Delta
Deal found 5/25![Delta logo]()
$154
This Super.com deal was found by Cheapflights users on 5/25. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/2910:10 pm
SFO
- MDW
1 stop11h 02m
Frontier
Deal found 5/25![Frontier logo]()
$158
Find flight deals from San Francisco to Midway
Discover tips and strategies to find the most affordable flight options for your journey from San Francisco (SFO) to Midway (MDW). 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 May 26, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $306 (Southwest) |
One-way from | $136 (Frontier) |
Popular in | December |
Cheapest in | January |
Average price | $372 |
Good round-trip deal | $391 or less |
Good one-way deal | $215 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from San Francisco 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 May 26, 2026.
Use the filters below to find and compare flights from San Francisco to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Fri 8/21
11:40 pm-5:50 am
Nonstop4h 10m
Chicago Midway
Tue 8/25
9:05 am-4:25 pm
1 stop9h 20m
$313
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Wed 7/8
12:15 pm-11:20 pm
1 stop9h 05m
Chicago Midway
Mon 7/13
5:10 am-11:20 am
1 stop8h 10m
$316
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Mon 7/6
2:15 pm-12:15 am
2 stops8h 00m
Chicago Midway
Tue 7/14
5:30 am-9:50 am
1 stop6h 20m
$337
Quickest round-trip
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Thu 9/10
5:35 am-11:40 am
Nonstop4h 05m
Chicago Midway
Sun 9/13
9:20 pm-11:55 pm
Nonstop4h 35m
$347
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Sat 8/8
11:40 pm-5:50 am
Nonstop4h 10m
Chicago Midway
Sat 8/15
6:00 pm-8:35 pm
Nonstop4h 35m
$353
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Tue 9/22
6:00 am-4:27 pm
1 stop8h 27m
Chicago Midway
Fri 9/25
6:45 pm-11:45 pm
1 stop7h 00m
$364
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Fri 9/4
12:40 pm-11:20 pm
1 stop8h 40m
Chicago Midway
Mon 9/7
5:30 am-11:35 am
1 stop8h 05m
$364
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Sat 7/4
5:00 am-2:35 pm
2 stops7h 35m
Chicago Midway
Tue 7/7
5:35 am-11:35 am
1 stop8h 00m
$369
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Fri 11/13
5:40 am-11:45 am
Nonstop4h 05m
Chicago Midway
Fri 11/20
6:30 am-12:25 pm
1 stop7h 55m
$372
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Thu 8/27
5:35 am-11:40 am
Nonstop4h 05m
Chicago Midway
Sun 8/30
8:30 pm-11:05 pm
Nonstop4h 35m
$380
Showing 1-10 of 22 resultsSorted by cheapest first
Compare providers for flights from San Francisco to Midway
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 San Francisco to Midway in May.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on San Francisco-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on San Francisco-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from San Francisco-Chicago Midway Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on San Francisco-Chicago Midway Airport 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 San Francisco-Chicago Midway Airport 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 San Francisco to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from San Francisco with our price prediction graph.
SFO-MDW
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from San Francisco to Chicago Midway Airport
Prices
Airlines
How far ahead should I book a flight from San Francisco to Chicago Midway Airport?
The best time to book flights from San Francisco to Chicago Midway Airport is 83 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest month to book a flight from San Francisco to Chicago Midway Airport?
Currently, January is the cheapest month in which you can book a flight from San Francisco to Chicago Midway Airport (average of $225). Flying from San Francisco to Chicago Midway Airport in December is currently the most expensive (average of $442). 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 SFO to MDW?
Find hourly flight availability from San Francisco 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 May 26, 2026.
It’s typically best to fly out from San Francisco to Chicago Midway Airport in the afternoon. Doing so could potentially save you 37% on the flight price compared to flying at noon, which is usually more expensive.
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 May 26, 2026.
Read through reviews of airlines operating flights from San Francisco to Chicago Midway Airport, such as Southwest,Delta, andUnited Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Boarding
8.1
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Boarding
8.1
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Boarding
8.1
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Boarding
8.1
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
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 to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Hammond
Porter
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Search flights from San Francisco to Midway by cabin class
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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 May 26, 2026.
San Francisco and Midway flights
Browse other San Francisco and Midway flight options. Last updated on May 26, 2026.
Other flights from San Francisco
Browse through other flights departing from San Francisco. Flights are based on user searches made on Cheapflights and were last updated on May 26, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 4 airlines flying from San Francisco to Midway
Discover the top 4 airlines that operate flights from San Francisco 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 May 26, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$147 | Average$267 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$207 | Average$477 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$225 | Average$421 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$252 | Average$434 | FlexibilityNo cancel fee | On-time63% |