$161+ 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 8/7. Fares are subject to change and may not be available on all flights or dates of travel.
SFO — MDW
Aug 13 — Aug 201
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 April, booked 84 days in advance, depart on a Wednesday or Monday and return on a Wednesday
Cheap flight deals from San Francisco to Midway
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Best
Last-minute
One-way
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 July 14, 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 July 14, 2026.
This Delta deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/212:12 am
SFO
- MDW
1 stop6h 27m
Delta
Thu 8/137:25 pm
MDW
- SFO
1 stop6h 22m
Delta
Deal found 7/13![Delta logo]()
$306
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/247:00 am
SFO
- MDW
2 stops8h 20m
Southwest
Thu 8/2711:05 am
MDW
- SFO
2 stops8h 50m
Southwest
Deal found 7/13![Southwest logo]()
$307
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:00 am
SFO
- MDW
2 stops9h 05m
Southwest
Wed 9/161:55 pm
MDW
- SFO
1 stop6h 20m
Southwest
Deal found 7/13![Southwest logo]()
$308
This Orbitz deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/1511:05 pm
SFO
- MDW
1 stop8h 46m
Frontier
Sun 8/1611:06 am
MDW
- SFO
1 stop10h 07m
Frontier
Deal found 7/13![Frontier logo]()
$309
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1611:40 pm
SFO
- MDW
Nonstop4h 10m
Southwest
Mon 10/193:45 pm
MDW
- SFO
2 stops8h 30m
Southwest
Deal found 7/13![Southwest logo]()
$310
This Frontier deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/410:10 pm
SFO
- MDW
1 stop9h 41m
Frontier
Wed 8/54:45 pm
MDW
- SFO
1 stop8h 09m
Frontier
Deal found 7/14![Frontier logo]()
$311
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/61:55 pm
SFO
- MDW
1 stop7h 25m
Southwest
Mon 8/105:40 am
MDW
- SFO
1 stop6h 30m
Southwest
Deal found 7/13![Southwest logo]()
$313
This Delta deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1312:12 am
SFO
- MDW
1 stop6h 27m
Delta
Wed 8/191:51 pm
MDW
- SFO
1 stop9h 11m
Delta
Deal found 7/13![Delta logo]()
$315
This Trip.com deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1010:48 pm
SFO
- MDW
1 stop10h 10m
Frontier
Sun 9/137:25 am
MDW
- SFO
1 stop12h 55m
Frontier
Deal found 7/12![Frontier logo]()
$316
This Frontier deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/511:05 pm
SFO
- MDW
1 stop8h 46m
Frontier
Wed 8/1211:06 am
MDW
- SFO
1 stop10h 07m
Frontier
Deal found 7/13![Frontier logo]()
$317
This Southwest deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” 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 8/55:40 am
SFO
- MDW
2 stops9h 30m
Southwest
Mon 8/105:40 am
MDW
- SFO
1 stop6h 30m
Southwest
Deal found 7/11![Southwest logo]()
$318
This Frontier deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/111:00 pm
SFO
- MDW
1 stop10h 07m
Frontier
Wed 8/126:05 am
MDW
- SFO
1 stop15h 08m
Frontier
Deal found 7/13![Frontier logo]()
$319
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 July 14, 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 July 14, 2026.
This Southwest deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” 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 8/86:10 am
SFO
- MDW
1 stop12h 05m
Southwest
Sat 8/1510:30 am
MDW
- SFO
Nonstop4h 30m
Southwest
Deal found 7/11![Southwest logo]()
$327
This Delta deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2310:59 pm
SFO
- MDW
1 stop8h 08m
Delta
Thu 10/17:13 pm
MDW
- SFO
1 stop6h 40m
Delta
Deal found 7/13![Delta logo]()
$348
This Southwest deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2411:40 pm
SFO
- MDW
Nonstop4h 10m
Southwest
Sun 9/278:30 pm
MDW
- SFO
Nonstop4h 35m
Southwest
Deal found 7/12![Southwest logo]()
$342
This Southwest deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” 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 8/311:40 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Sat 8/1510:30 am
MDW
- SFO
Nonstop4h 30m
Southwest
Deal found 7/11![Southwest logo]()
$344
This Southwest deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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 8/67:10 pm
SFO
- MDW
1 stop7h 20m
Southwest
Mon 8/106:15 pm
MDW
- SFO
1 stop6h 50m
Southwest
Deal found 7/9![Southwest logo]()
$355
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:10 am
SFO
- MDW
1 stop12h 05m
Southwest
Sun 8/168:30 pm
MDW
- SFO
Nonstop4h 35m
Southwest
Deal found 7/13![Southwest logo]()
$358
This Southwest deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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 8/137:00 am
SFO
- MDW
2 stops8h 20m
Southwest
Fri 8/1412:15 pm
MDW
- SFO
1 stop9h 00m
Southwest
Deal found 7/9![Southwest logo]()
$365
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 8/166:50 am
SFO
- MDW
2 stops8h 05m
Southwest
Tue 8/1810:30 am
MDW
- SFO
2 stops7h 30m
Southwest
Deal found 7/10![Southwest logo]()
$370
This Southwest deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/211:40 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Wed 8/51:55 pm
MDW
- SFO
1 stop6h 20m
Southwest
Deal found 7/12![Southwest logo]()
$372
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 11/116:15 am
SFO
- MDW
2 stops8h 50m
Southwest
Sun 11/155:20 pm
MDW
- SFO
2 stops8h 00m
Southwest
Deal found 7/10![Southwest logo]()
$379
This Southwest deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” 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 8/211:40 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Fri 8/79:10 pm
MDW
- SFO
Nonstop4h 35m
Southwest
Deal found 7/11![Southwest logo]()
$380
Last-minute flights from San Francisco to MidwayDiscover last-minute flight deals from San Francisco to Midway. Data last updated July 14, 2026 and is based on user searches.
Discover last-minute flight deals from San Francisco to Midway. Data last updated July 14, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/3111:00 pm
SFO
- MDW
1 stop10h 07m
Frontier
Mon 8/316:05 am
MDW
- SFO
1 stop14h 58m
Frontier
Deal found 7/14![Frontier logo]()
$313
This Frontier deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/111:00 pm
SFO
- MDW
1 stop10h 07m
Frontier
Wed 8/126:05 am
MDW
- SFO
1 stop15h 08m
Frontier
Deal found 7/13![Frontier logo]()
$319
This Delta deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/212:12 am
SFO
- MDW
1 stop6h 27m
Delta
Thu 8/137:25 pm
MDW
- SFO
1 stop6h 22m
Delta
Deal found 7/13![Delta logo]()
$306
This CheapOair deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/412:54 am
SFO
- MDW
1 stop12h 56m
Frontier
Tue 8/1111:06 am
MDW
- SFO
1 stop10h 07m
Frontier
Deal found 7/14![Frontier logo]()
$304
This Super.com deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/410:10 pm
SFO
- MDW
1 stop9h 41m
Frontier
Fri 8/711:06 am
MDW
- SFO
1 stop10h 07m
Frontier
Deal found 7/14![Frontier logo]()
$311
This Frontier deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/511:05 pm
SFO
- MDW
1 stop8h 46m
Frontier
Wed 8/1211:06 am
MDW
- SFO
1 stop10h 07m
Frontier
Deal found 7/13![Frontier logo]()
$317
This Southwest deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” 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 8/55:40 am
SFO
- MDW
2 stops9h 30m
Southwest
Mon 8/105:40 am
MDW
- SFO
1 stop6h 30m
Southwest
Deal found 7/11![Southwest logo]()
$318
This Kiwi.com deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/811:05 pm
SFO
- MDW
1 stop8h 46m
Frontier
Tue 8/115:46 pm
MDW
- SFO
2 stops18h 39m
Frontier
Deal found 7/14![Frontier logo]()
$305
This Delta deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1312:12 am
SFO
- MDW
1 stop6h 27m
Delta
Wed 8/191:51 pm
MDW
- SFO
1 stop9h 11m
Delta
Deal found 7/13![Delta logo]()
$315
This Orbitz deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/1511:05 pm
SFO
- MDW
1 stop8h 46m
Frontier
Sun 8/1611:06 am
MDW
- SFO
1 stop10h 07m
Frontier
Deal found 7/13![Frontier logo]()
$309
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/247:00 am
SFO
- MDW
2 stops8h 20m
Southwest
Thu 8/2711:05 am
MDW
- SFO
2 stops8h 50m
Southwest
Deal found 7/13![Southwest logo]()
$307
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/286:00 am
SFO
- MDW
2 stops9h 05m
Southwest
Mon 8/319:10 pm
MDW
- SFO
Nonstop4h 35m
Southwest
Deal found 7/13![Southwest logo]()
$310
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 July 14, 2026.
Search for one-way flight options from San Francisco to Midway. Find affordable one-way fares based on user searches. Data last updated July 14, 2026.
This Expedia deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/711:05 pm
SFO
- MDW
1 stop8h 46m
Frontier
Deal found 7/14![Frontier logo]()
$161
This CheapOair deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/210:35 pm
SFO
- MDW
1 stop10h 20m
Frontier
Deal found 7/14![Frontier logo]()
$162
This Frontier deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/3010:35 pm
SFO
- MDW
1 stop10h 20m
Frontier
Deal found 7/13![Frontier logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1310:23 pm
SFO
- MDW
2 stops16h 59m
Frontier
Deal found 7/14![Frontier logo]()
$164
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/115:35 am
SFO
- MDW
Nonstop4h 05m
Southwest
Deal found 7/13![Southwest logo]()
$165
This Frontier deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/412:54 am
SFO
- MDW
1 stop12h 56m
Frontier
Deal found 7/14![Frontier logo]()
$167
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/311:40 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Deal found 7/13![Southwest logo]()
$168
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/31:55 pm
SFO
- MDW
1 stop7h 25m
Southwest
Deal found 7/13![Southwest logo]()
$169
This Delta deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/156:00 am
SFO
- MDW
1 stop8h 39m
Delta
Deal found 7/13![Delta logo]()
$170
This Super.com deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” 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.
Tue 7/2110:10 pm
SFO
- MDW
1 stop10h 57m
Frontier
Deal found 7/11![Frontier logo]()
$171
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 July 14, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $306 (Delta) |
One-way from | $161 (Expedia) |
Popular in | October |
Cheapest in | January |
Average price | $442 |
Good round-trip deal | $403 or less |
Good one-way deal | $203 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 July 14, 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
Sat 8/8
6:10 am-8:15 pm
1 stop12h 05m
Chicago Midway
Sat 8/15
10:30 am-1:00 pm
Nonstop4h 30m
$327
Quickest round-trip
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Thu 9/24
11:40 pm-5:50 am
Nonstop4h 10m
Chicago Midway
Sun 9/27
8:30 pm-11:05 pm
Nonstop4h 35m
$342
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Mon 8/3
11:40 pm-5:55 am
Nonstop4h 15m
Chicago Midway
Sat 8/15
10:30 am-1:00 pm
Nonstop4h 30m
$344
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Wed 9/23
10:59 pm-9:07 am
1 stop8h 08m
Chicago Midway
Thu 10/1
7:13 pm-11:53 pm
1 stop6h 40m
$348
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Thu 8/6
7:10 pm-4:30 am
1 stop7h 20m
Chicago Midway
Mon 8/10
6:15 pm-11:05 pm
1 stop6h 50m
$355
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Sat 8/15
6:10 am-8:15 pm
1 stop12h 05m
Chicago Midway
Sun 8/16
8:30 pm-11:05 pm
Nonstop4h 35m
$358
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Thu 8/13
7:00 am-5:20 pm
2 stops8h 20m
Chicago Midway
Fri 8/14
12:15 pm-7:15 pm
1 stop9h 00m
$365
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Sun 8/16
6:50 am-4:55 pm
2 stops8h 05m
Chicago Midway
Tue 8/18
10:30 am-4:00 pm
2 stops7h 30m
$370
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Sun 8/2
11:40 pm-5:55 am
Nonstop4h 15m
Chicago Midway
Wed 8/5
1:55 pm-6:15 pm
1 stop6h 20m
$372
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Wed 11/11
6:15 am-5:05 pm
2 stops8h 50m
Chicago Midway
Sun 11/15
5:20 pm-11:20 pm
2 stops8h 00m
$379
Showing 1-10 of 20 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 July.
| 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 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 $266). Flying from San Francisco to Chicago Midway Airport in October is currently the most expensive (average of $577). 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 July 14, 2026.
When flying from San Francisco to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
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 July 14, 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
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
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
Valparaiso
Hammond
Saint Joseph
Porter
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Alternative routes for San Francisco to Midway
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Complete your trip
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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 July 14, 2026.
San Francisco and Midway flights
Browse other San Francisco and Midway flight options. Last updated on July 14, 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 July 14, 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 July 14, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$207 | Average$477 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$213 | Average$275 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$225 | Average$518 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$253 | Average$426 | FlexibilityNo cancel fee | On-time63% |