$111+ 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 5/8. Fares are subject to change and may not be available on all flights or dates of travel.
SFO — MDW
Apr 25 — May 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
Cheapest
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 March 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 March 26, 2026.
This Expedia deal was found by Cheapflights users on 3/25. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/1111:52 pm
SFO
- MDW
1 stop12h 15m
Frontier
Mon 6/153:02 pm
MDW
- SFO
1 stop9h 55m
Frontier
Deal found 3/25![Frontier logo]()
$250
This Southwest deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/1611:25 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Wed 4/224:00 pm
MDW
- SFO
2 stops9h 15m
Southwest
Deal found 3/26![Southwest logo]()
$251
This Southwest deal was found by Cheapflights users on 3/23. 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 4/1311:25 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Tue 4/2112:50 pm
MDW
- SFO
2 stops10h 35m
Southwest
Deal found 3/23![Southwest logo]()
$252
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/611:25 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Sat 5/96:00 am
MDW
- SFO
1 stop6h 25m
Southwest
Deal found 3/24![Southwest logo]()
$253
This Southwest deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/145:25 am
SFO
- MDW
Nonstop4h 10m
Southwest
Tue 4/216:45 am
MDW
- SFO
1 stop7h 50m
Southwest
Deal found 3/26![Southwest logo]()
$256
This Kiwi.com deal was found by Cheapflights users on 3/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/811:59 pm
SFO
- MDW
1 stop12h 13m
Frontier
Fri 5/153:07 pm
MDW
- SFO
2 stops29h 23m
Frontier
Deal found 3/23![Frontier logo]()
$257
This Delta deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2810:55 pm
SFO
- MDW
1 stop7h 52m
Delta
Mon 5/47:16 pm
MDW
- SFO
1 stop6h 38m
Delta
Deal found 3/26![Delta logo]()
$258
This Delta deal was found by Cheapflights users on 3/25. 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 4/1610:55 pm
SFO
- MDW
1 stop7h 52m
Delta
Wed 4/227:16 pm
MDW
- SFO
1 stop6h 38m
Delta
Deal found 3/25![Delta logo]()
$259
This Southwest deal was found by Cheapflights users on 3/22. 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 5/611:25 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Wed 5/139:00 pm
MDW
- SFO
Nonstop4h 35m
Southwest
Deal found 3/22![Southwest logo]()
$263
This Delta deal was found by Cheapflights users on 3/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/1410:55 pm
SFO
- MDW
1 stop7h 52m
Delta
Sat 4/181:24 pm
MDW
- SFO
1 stop7h 39m
Delta
Deal found 3/23![Delta logo]()
$264
This Frontier deal was found by Cheapflights users on 3/25. 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.
Sun 5/1710:15 pm
SFO
- MDW
1 stop10h 54m
Frontier
Mon 5/183:07 pm
MDW
- SFO
1 stop9h 57m
Frontier
Deal found 3/25![Frontier logo]()
$265
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 March 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 March 26, 2026.
This Southwest deal was found by Cheapflights users on 3/23. 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 4/1311:25 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Tue 4/2112:50 pm
MDW
- SFO
2 stops10h 35m
Southwest
Deal found 3/23![Southwest logo]()
$252
This Delta deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/612:20 am
SFO
- MDW
1 stop6h 22m
Delta
Tue 5/121:59 pm
MDW
- SFO
1 stop8h 38m
Delta
Deal found 3/25![Delta logo]()
$258
This Southwest deal was found by Cheapflights users on 3/25. 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 5/2311:25 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Sat 5/305:10 am
MDW
- SFO
1 stop8h 40m
Southwest
Deal found 3/25![Southwest logo]()
$269
This Southwest deal was found by Cheapflights users on 3/23. 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.
Tue 6/211:25 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Mon 6/89:30 pm
MDW
- SFO
Nonstop4h 40m
Southwest
Deal found 3/23![Southwest logo]()
$275
This Southwest deal was found by Cheapflights users on 3/25. 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.
Thu 4/166:20 am
SFO
- MDW
2 stops9h 35m
Southwest
Wed 4/223:00 pm
MDW
- SFO
1 stop7h 55m
Southwest
Deal found 3/25![Southwest logo]()
$299
This Delta deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/512:48 am
SFO
- MDW
1 stop5h 49m
Delta
Fri 7/177:06 pm
MDW
- SFO
1 stop6h 40m
Delta
Deal found 3/24![Delta logo]()
$364
This Southwest deal was found by Cheapflights users on 3/21. 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 4/1811:25 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Sat 4/256:10 pm
MDW
- SFO
Nonstop4h 35m
Southwest
Deal found 3/21![Southwest logo]()
$313
This Southwest deal was found by Cheapflights users on 3/22. 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 6/912:10 pm
SFO
- MDW
2 stops8h 55m
Southwest
Tue 6/163:10 pm
MDW
- SFO
2 stops9h 05m
Southwest
Deal found 3/22![Southwest logo]()
$323
This Southwest deal was found by Cheapflights users on 3/21. 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 7/2411:40 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Mon 7/279:30 pm
MDW
- SFO
Nonstop4h 40m
Southwest
Deal found 3/21![Southwest logo]()
$353
This Southwest deal was found by Cheapflights users on 3/23. 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.
Fri 6/193:10 pm
SFO
- MDW
1 stop7h 50m
Southwest
Fri 7/1010:05 am
MDW
- SFO
Nonstop4h 30m
Southwest
Deal found 3/23![Southwest logo]()
$363
This Southwest deal was found by Cheapflights users on 3/25. 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 5/411:25 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Sun 5/109:35 pm
MDW
- SFO
Nonstop4h 35m
Southwest
Deal found 3/25![Southwest logo]()
$372
This Southwest deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/306:00 am
SFO
- MDW
2 stops8h 55m
Southwest
Thu 7/95:20 am
MDW
- SFO
2 stops8h 00m
Southwest
Deal found 3/25![Southwest logo]()
$383
Last-minute flights from San Francisco to MidwayDiscover last-minute flight deals from San Francisco to Midway. Data last updated March 26, 2026 and is based on user searches.
Discover last-minute flight deals from San Francisco to Midway. Data last updated March 26, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 3/23. 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 4/1311:25 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Tue 4/2112:50 pm
MDW
- SFO
2 stops10h 35m
Southwest
Deal found 3/23![Southwest logo]()
$252
This Southwest deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/145:25 am
SFO
- MDW
Nonstop4h 10m
Southwest
Tue 4/216:45 am
MDW
- SFO
1 stop7h 50m
Southwest
Deal found 3/26![Southwest logo]()
$256
This Delta deal was found by Cheapflights users on 3/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/1410:55 pm
SFO
- MDW
1 stop7h 52m
Delta
Mon 4/207:16 pm
MDW
- SFO
1 stop6h 38m
Delta
Deal found 3/23![Delta logo]()
$264
This Southwest deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/165:15 am
SFO
- MDW
Nonstop4h 10m
Southwest
Wed 4/224:00 pm
MDW
- SFO
2 stops9h 15m
Southwest
Deal found 3/26![Southwest logo]()
$251
This Delta deal was found by Cheapflights users on 3/25. 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 4/1610:55 pm
SFO
- MDW
1 stop7h 52m
Delta
Wed 4/227:16 pm
MDW
- SFO
1 stop6h 38m
Delta
Deal found 3/25![Delta logo]()
$259
This Southwest deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/1611:25 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Mon 4/205:15 pm
MDW
- SFO
1 stop7h 50m
Southwest
Deal found 3/26![Southwest logo]()
$269
This Southwest deal was found by Cheapflights users on 3/25. 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 4/1711:25 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Tue 4/219:00 pm
MDW
- SFO
Nonstop4h 35m
Southwest
Deal found 3/25![Southwest logo]()
$267
This Southwest deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/227:40 pm
SFO
- MDW
1 stop6h 55m
Southwest
Wed 4/294:00 pm
MDW
- SFO
2 stops9h 15m
Southwest
Deal found 3/25![Southwest logo]()
$268
This Priceline deal was found by Cheapflights users on 3/25. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2311:16 pm
SFO
- MDW
1 stop11h 14m
Frontier
Mon 4/276:00 am
MDW
- SFO
1 stop13h 34m
Frontier
Deal found 3/25![Frontier logo]()
$250
This Delta deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2810:55 pm
SFO
- MDW
1 stop7h 52m
Delta
Mon 5/47:16 pm
MDW
- SFO
1 stop6h 38m
Delta
Deal found 3/26![Delta logo]()
$258
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 March 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 March 26, 2026.
This Frontier deal was found by Cheapflights users on 3/23. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/811:59 pm
SFO
- MDW
1 stop12h 13m
Frontier
Deal found 3/23![Frontier logo]()
$111
This Frontier deal was found by Cheapflights users on 3/23. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/511:59 pm
SFO
- MDW
1 stop12h 13m
Frontier
Deal found 3/23![Frontier logo]()
$112
This Kiwi.com deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/227:40 pm
SFO
- MDW
2 stops24h 42m
Frontier
Deal found 3/25![Frontier logo]()
$114
This Kiwi.com deal was found by Cheapflights users on 3/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/216:29 pm
SFO
- MDW
2 stops42h 35m
Frontier
Deal found 3/23![Frontier logo]()
$115
This Southwest deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2810:40 pm
SFO
- MDW
1 stop7h 45m
Southwest
Deal found 3/26![Southwest logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/277:15 pm
SFO
- MDW
2 stops13h 57m
Frontier
Deal found 3/26![Frontier logo]()
$118
This Delta deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/226:00 am
SFO
- MDW
1 stop8h 26m
Delta
Deal found 3/26![Delta logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/287:40 pm
SFO
- MDW
2 stops21h 51m
Frontier
Deal found 3/25![Frontier logo]()
$120
This Super.com deal was found by Cheapflights users on 3/24. 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.
Wed 5/2010:15 pm
SFO
- MDW
1 stop10h 57m
Frontier
Deal found 3/24![Frontier logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 3/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2010:38 pm
SFO
- MDW
2 stops36h 22m
Frontier
Deal found 3/23![Frontier logo]()
$124
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 March 26, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $250 (Expedia) |
One-way from | $111 (Frontier) |
Popular in | December |
Cheapest in | January |
Average price | $397 |
Good round-trip deal | $343 or less |
Good one-way deal | $192 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 March 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
Mon 4/13
11:25 pm-5:40 am
Nonstop4h 15m
Chicago Midway
Tue 4/21
12:50 pm-9:25 pm
2 stops10h 35m
$252
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Wed 5/6
12:20 am-8:42 am
1 stop6h 22m
Chicago Midway
Tue 5/12
1:59 pm-8:37 pm
1 stop8h 38m
$258
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Sat 5/23
11:25 pm-5:40 am
Nonstop4h 15m
Chicago Midway
Sat 5/30
5:10 am-11:50 am
1 stop8h 40m
$269
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Tue 6/2
11:25 pm-5:40 am
Nonstop4h 15m
Chicago Midway
Mon 6/8
9:30 pm-12:10 am
Nonstop4h 40m
$275
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Thu 4/16
6:20 am-5:55 pm
2 stops9h 35m
Chicago Midway
Wed 4/22
3:00 pm-8:55 pm
1 stop7h 55m
$299
Quickest round-trip
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Sat 4/18
11:25 pm-5:40 am
Nonstop4h 15m
Chicago Midway
Sat 4/25
6:10 pm-8:45 pm
Nonstop4h 35m
$313
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Tue 6/9
12:10 pm-11:05 pm
2 stops8h 55m
Chicago Midway
Tue 6/16
3:10 pm-10:15 pm
2 stops9h 05m
$323
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Fri 7/24
11:40 pm-5:55 am
Nonstop4h 15m
Chicago Midway
Mon 7/27
9:30 pm-12:10 am
Nonstop4h 40m
$353
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Fri 6/19
3:10 pm-1:00 am
1 stop7h 50m
Chicago Midway
Fri 7/10
10:05 am-12:35 pm
Nonstop4h 30m
$363
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Sun 7/5
12:48 am-8:37 am
1 stop5h 49m
Chicago Midway
Fri 7/17
7:06 pm-11:46 pm
1 stop6h 40m
$364
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 March.
| 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 Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy1 star | 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?
Use this chart to determine the optimal time to book a round-trip flight from San Francisco to Midway. Price data was last updated on March 13, 2026.
The best time to book flights from San Francisco to Chicago Midway Airport is 84 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, August is the cheapest month in which you can book a flight from San Francisco to Chicago Midway Airport (average of $151). Flying from San Francisco to Chicago Midway Airport in June is currently the most expensive (average of $247). 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 March 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 48% 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 March 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.
Food
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Food
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Food
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Food
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Food
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
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 locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
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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 March 26, 2026.
San Francisco and Midway flights
Browse other San Francisco and Midway flight options. Last updated on March 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 March 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 March 26, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$133 | Average$435 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$147 | Average$254 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$237 | Average$400 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$241 | Average$358 | FlexibilityNo cancel fee | On-timeN/A |