$154+ Cheap flights from Midway (MDW) to San Francisco (SFO)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/18. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SFO
Nov 24 — Dec 11
Round-trip
1 adult, Economy
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Find cheap flights from Midway to San Francisco with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Midway to San Francisco
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Best
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One-way
Cheapest flights from Midway to San FranciscoExplore the most affordable flight options available from Midway to San Francisco. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 25, 2026.
Explore the most affordable flight options available from Midway to San Francisco. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 25, 2026.
This Southwest deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/21:20 pm -
2 stops10h 55m
Sat 12/510:40 am -
1 stop8h 10m
Deal found 10/20![Southwest logo]()
$268
This Southwest deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/196:05 am -
1 stop7h 05m
Thu 11/266:35 am -
1 stop8h 15m
Deal found 10/20![Southwest logo]()
$269
This Southwest deal was found by Cheapflights users on 10/21. 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 11/109:05 pm -
Nonstop4h 50m
Fri 11/1311:35 pm -
Nonstop4h 25m
Deal found 10/21![Southwest logo]()
$270
This Southwest deal was found by Cheapflights users on 10/24. 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.
Tue 12/151:20 pm -
2 stops10h 05m
Sat 1/239:15 am -
2 stops9h 00m
Deal found 10/24![Southwest logo]()
$271
This Trip.com deal was found by Cheapflights users on 10/22. 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.
Sat 11/77:15 am -
1 stop15h 35m
Wed 11/1111:47 pm -
1 stop9h 38m
Deal found 10/22![Frontier logo]()
$272
This Kiwi.com deal was found by Cheapflights users on 10/23. 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.
Wed 11/1112:27 pm -
1 stop12h 02m
Wed 11/189:14 am -
2 stops24h 11m
Deal found 10/23![Frontier logo]()
$274
This CheapOair deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/412:27 pm -
1 stop12h 02m
Wed 11/1111:47 pm -
1 stop9h 38m
Deal found 10/20![Frontier logo]()
$276
This Kiwi.com deal was found by Cheapflights users on 10/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1012:27 pm -
1 stop12h 02m
Mon 11/1611:47 pm -
1 stop9h 35m
Deal found 10/24![Frontier logo]()
$277
This Southwest deal was found by Cheapflights users on 10/24. 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 11/119:05 pm -
Nonstop4h 50m
Mon 11/169:25 pm -
1 stop9h 35m
Deal found 10/24![Southwest logo]()
$278
This Southwest deal was found by Cheapflights users on 10/23. 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 11/239:30 pm -
Nonstop4h 55m
Sat 12/58:15 am -
Nonstop4h 05m
Deal found 10/23![Southwest logo]()
$279
Best flights from Midway to San FranciscoDiscover carefully curated flight deals from Midway to San Francisco that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 25, 2026.
Discover carefully curated flight deals from Midway to San Francisco that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 25, 2026.
This Southwest deal was found by Cheapflights users on 10/24. 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 12/179:30 pm -
Nonstop4h 55m
Fri 1/155:50 am -
Nonstop4h 05m
Deal found 10/24![Southwest logo]()
$297
This Delta deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/235:29 pm -
1 stop8h 32m
Fri 12/46:35 pm -
2 stops20h 15m
Deal found 10/20![Delta logo]()
$314
This Southwest deal was found by Cheapflights users on 10/24. 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.
Fri 2/59:40 pm -
Nonstop4h 50m
Tue 2/911:55 pm -
Nonstop4h 10m
Deal found 10/24![Southwest logo]()
$297
This Southwest deal was found by Cheapflights users on 10/24. 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.
Sat 11/147:40 am -
2 stops9h 30m
Sat 12/511:35 pm -
Nonstop4h 25m
Deal found 10/24![Southwest logo]()
$312
This Delta deal was found by Cheapflights users on 10/23. 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.
Thu 11/195:13 pm -
1 stop8h 45m
Mon 11/2311:35 pm -
1 stop7h 15m
Deal found 10/23![Delta logo]()
$344
This Delta deal was found by Cheapflights users on 10/24. 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.
Wed 12/236:30 pm -
1 stop7h 36m
Mon 12/286:20 am -
1 stop9h 04m
Deal found 10/24![Delta logo]()
$361
This Southwest deal was found by Cheapflights users on 10/21. 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.
Thu 12/177:25 am -
1 stop7h 40m
Wed 12/239:10 pm -
1 stop6h 45m
Deal found 10/21![Southwest logo]()
$343
This Delta deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/159:30 am -
1 stop6h 56m
Tue 11/1711:35 pm -
1 stop7h 15m
Deal found 10/20![Delta logo]()
$370
This Southwest deal was found by Cheapflights users on 10/22. 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 11/2410:25 pm -
Nonstop4h 55m
Mon 11/309:10 pm -
1 stop6h 45m
Deal found 10/22![Southwest logo]()
$346
This Southwest deal was found by Cheapflights users on 10/23. 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 12/174:00 pm -
1 stop9h 00m
Fri 12/185:25 am -
2 stops8h 15m
Deal found 10/23![Southwest logo]()
$358
This Delta deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/141:00 pm -
1 stop7h 48m
Fri 4/1612:40 am -
1 stop6h 09m
Deal found 10/20![Delta logo]()
$405
Last-minute flights from Midway to San FranciscoDiscover last-minute flight deals from Midway to San Francisco. Data last updated October 25, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to San Francisco. Data last updated October 25, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/412:27 pm -
1 stop12h 02m
Wed 11/1111:47 pm -
1 stop9h 38m
Deal found 10/20![Frontier logo]()
$276
This Trip.com deal was found by Cheapflights users on 10/22. 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.
Sat 11/77:15 am -
1 stop15h 35m
Wed 11/1111:47 pm -
1 stop9h 38m
Deal found 10/22![Frontier logo]()
$272
This Southwest deal was found by Cheapflights users on 10/21. 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 11/109:05 pm -
Nonstop4h 50m
Fri 11/1311:35 pm -
Nonstop4h 25m
Deal found 10/21![Southwest logo]()
$270
This Kiwi.com deal was found by Cheapflights users on 10/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1012:27 pm -
1 stop12h 02m
Mon 11/1611:47 pm -
1 stop9h 35m
Deal found 10/24![Frontier logo]()
$277
This Kiwi.com deal was found by Cheapflights users on 10/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1112:27 pm -
1 stop12h 02m
Tue 11/1711:47 pm -
1 stop9h 35m
Deal found 10/24![Frontier logo]()
$273
This Kiwi.com deal was found by Cheapflights users on 10/23. 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.
Wed 11/1112:27 pm -
1 stop12h 02m
Wed 11/189:14 am -
2 stops24h 11m
Deal found 10/23![Frontier logo]()
$274
This Southwest deal was found by Cheapflights users on 10/24. 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 11/119:05 pm -
Nonstop4h 50m
Mon 11/169:25 pm -
1 stop9h 35m
Deal found 10/24![Southwest logo]()
$278
This Southwest deal was found by Cheapflights users on 10/21. 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.
Thu 11/126:30 am -
1 stop7h 55m
Wed 11/1811:35 am -
1 stop9h 10m
Deal found 10/21![Southwest logo]()
$268
This Southwest deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/196:05 am -
1 stop7h 05m
Thu 11/266:35 am -
1 stop8h 15m
Deal found 10/20![Southwest logo]()
$269
This Southwest deal was found by Cheapflights users on 10/23. 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 11/239:30 pm -
Nonstop4h 55m
Sat 12/58:15 am -
Nonstop4h 05m
Deal found 10/23![Southwest logo]()
$279
One-way flights from Midway to San FranciscoSearch for one-way flight options from Midway to San Francisco. Find affordable one-way fares based on user searches. Data last updated October 25, 2026.
Search for one-way flight options from Midway to San Francisco. Find affordable one-way fares based on user searches. Data last updated October 25, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/186:01 am -
2 stops16h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Frontier logo]()
$154
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/301:16 pm -
2 stops46h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Frontier logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1612:20 pm -
2 stops31h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Frontier logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 10/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/166:01 am -
1 stop29h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Frontier logo]()
$158
This Delta deal was found by Cheapflights users on 10/24. 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.
Thu 12/175:30 pm -
1 stop8h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Delta logo]()
$159
This Delta deal was found by Cheapflights users on 10/23. 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.
Wed 11/255:29 pm -
1 stop8h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Delta logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/96:42 pm -
2 stops29h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Frontier logo]()
$161
This Super.com deal was found by Cheapflights users on 10/24. 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.
Sat 11/712:20 pm -
1 stop12h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Frontier logo]()
$163
This Super.com deal was found by Cheapflights users on 10/24. 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.
Thu 11/1912:20 pm -
1 stop12h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Frontier logo]()
$164
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/46:16 am -
1 stop13h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Frontier logo]()
$165
Find flight deals from Midway to San Francisco
Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to San Francisco (SFO). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated October 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $268 (Southwest) |
One-way from | $154 (Kiwi.com) |
Popular in | November |
Cheapest in | April |
Average price | $374 |
Good round-trip deal | $338 or less |
Good one-way deal | $248 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to San Francisco that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 25, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to San Francisco that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSan Francisco
MDW Chicago Midway - SFO San Francisco
MDWSFO
Chicago Midway
Tue 12/8
11:28 am-7:01 pm
1 stop9h 33m
San Francisco
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$159
ChicagoSan Francisco
MDW Chicago Midway - SFO San Francisco
MDWSFO
Chicago Midway
Sun 1/31
3:20 pm-7:45 pm
1 stop6h 25m
San Francisco
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$159
ChicagoSan Francisco
MDW Chicago Midway - SFO San Francisco
MDWSFO
Chicago Midway
Wed 11/25
5:29 pm-12:01 am
1 stop8h 32m
San Francisco
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$159
ChicagoSan Francisco
MDW Chicago Midway - SFO San Francisco
MDWSFO
Chicago Midway
Fri 12/18
7:35 am-12:20 pm
1 stop6h 45m
San Francisco
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$159
ChicagoSan Francisco
MDW Chicago Midway - SFO San Francisco
MDWSFO
Chicago Midway
Sun 12/6
5:15 am-10:50 am
1 stop7h 35m
San Francisco
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$159
ChicagoSan Francisco
MDW Chicago Midway - SFO San Francisco
MDWSFO
Chicago Midway
Sat 12/19
8:05 pm-12:25 am
1 stop6h 20m
San Francisco
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$159
Quickest round-trip
ChicagoSan Francisco
MDW Chicago Midway - SFO San Francisco
MDWSFO
Chicago Midway
Sat 1/9
10:00 am-12:50 pm
Nonstop4h 50m
San Francisco
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$199
ChicagoSan Francisco
MDW Chicago Midway - SFO San Francisco
MDWSFO
Chicago Midway
Tue 11/24
10:25 pm-1:20 am
Nonstop4h 55m
San Francisco
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$199
ChicagoSan Francisco
MDW Chicago Midway - SFO San Francisco
MDWSFO
Chicago Midway
Wed 12/23
10:25 pm-1:20 am
Nonstop4h 55m
San Francisco
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$212
ChicagoSan Francisco
MDW Chicago Midway - SFO San Francisco
MDWSFO
Chicago Midway
Thu 12/24
9:05 pm-11:55 pm
Nonstop4h 50m
San Francisco
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$212
Showing 1-10 of 21 resultsSorted by cheapest first
Compare providers for flights from Midway to San Francisco
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to San Francisco in October.
| 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 Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago Midway Airport-San Francisco flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-San Francisco flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-San Francisco flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago Midway Airport-San Francisco flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-San Francisco flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Midway to San Francisco
Have a flexible travel schedule? Discover the best time to fly to San Francisco from Midway with our price prediction graph.
MDW-SFO
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago Midway Airport to San Francisco
Prices
Delays
What is the cheapest month to book a flight from Chicago Midway Airport to San Francisco?
Currently, April is the cheapest month in which you can book a flight from Chicago Midway Airport to San Francisco (average of $288). Flying from Chicago Midway Airport to San Francisco in November is currently the most expensive (average of $560). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from MDW to SFO?
Find hourly flight availability from Midway to San Francisco. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 25, 2026.
It’s typically best to fly out from Chicago Midway Airport to San Francisco in the evening. Doing so could potentially save you 35% on the flight price compared to flying at noon, which is usually more expensive.
What is the cheapest day to fly from Chicago Midway Airport to San Francisco?
Use this chart to determine the cheapest time to fly round-trip from Midway to San Francisco. Price data was last updated on October 17, 2026.
Travelers seeking maximum savings on their Chicago Midway Airport to San Francisco flight should consider departing on Tuesday afternoons when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
How often are flights from Chicago to San Francisco delayed?
About 43% of weekly flights between Chicago and San Francisco have experienced delays in the past year, with the average delay time being 130 minutes.
What is the most punctual flight time for Chicago to San Francisco flights?
Historically, flights departing in the early afternoon are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Saturday tends to have the lowest number of delays on this route, whereas Friday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to San Francisco flights?
Over the last year, Southwest have had the lowest number of delays on this route, with just 43% of flights being delayed.
Reviews of airlines servicing San Francisco
Get insights into the airlines that provide service to San Francisco. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to San Francisco. Reviews last updated October 25, 2026.
Read reviews from past customers who have flown Southwest from Chicago Midway Airport to San Francisco. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Entertainment
7.4
Comfort
8.0
Boarding
8.1
Food
7.0
Overall
7.9
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Crew
8.6
Entertainment
7.4
Comfort
8.0
Boarding
8.1
Food
7.0
Overall
7.9
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Related info for your journey
Find useful and relevant information for your journey from Midway to San Francisco. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near San Francisco?
Book flights to San Francisco if you plan to visit one of these locationsSouth San Francisco
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Emeryville
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| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$257 | Average$394 | FlexibilityNo cancel fee | On-time63% |