$123+ Cheap flights from San Francisco (SFO) to Midway (MDW)
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 11/9. Fares are subject to change and may not be available on all flights or dates of travel.
SFO — MDW
Nov 8 — Nov 151
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 14 days in advance, depart on a Wednesday or Monday 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 October 9, 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 October 9, 2026.
This Southwest deal was found by Cheapflights users on 10/6. 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 10/286:50 pm -
2 stops8h 50m
Sat 10/3112:50 pm -
2 stops7h 25m
Deal found 10/6![Southwest logo]()
$262
This Kiwi.com deal was found by Cheapflights users on 10/5. 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 10/2611:59 pm -
1 stop9h 23m
Fri 10/3012:20 pm -
1 stop12h 09m
Deal found 10/5![Frontier logo]()
$265
This Southwest deal was found by Cheapflights users on 10/8. 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 10/296:00 am -
2 stops7h 10m
Sat 10/3112:50 pm -
2 stops7h 25m
Deal found 10/8![Southwest logo]()
$267
This Frontier deal was found by Cheapflights users on 10/5. 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 10/2011:59 pm -
1 stop12h 36m
Fri 11/612:20 pm -
1 stop12h 44m
Deal found 10/5![Frontier logo]()
$268
This Kiwi.com deal was found by Cheapflights users on 10/8. 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 11/139:09 am -
2 stops12h 38m
Sat 11/1412:20 pm -
1 stop12h 09m
Deal found 10/8![Frontier logo]()
$270
This Southwest deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1311:35 pm -
Nonstop4h 25m
Mon 11/169:05 pm -
Nonstop4h 50m
Deal found 10/7![Southwest logo]()
$271
This Southwest deal was found by Cheapflights users on 10/5. 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 12/411:35 pm -
Nonstop4h 25m
Mon 12/79:05 pm -
Nonstop4h 50m
Deal found 10/5![Southwest logo]()
$272
This Kiwi.com deal was found by Cheapflights users on 10/8. 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 10/277:14 pm -
2 stops14h 08m
Fri 10/3012:20 pm -
1 stop12h 09m
Deal found 10/8![Frontier logo]()
$273
This Super.com deal was found by Cheapflights users on 10/5. 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 10/1311:59 pm -
1 stop12h 36m
Thu 10/151:12 pm -
1 stop11h 13m
Deal found 10/5![Frontier logo]()
$274
This Kiwi.com deal was found by Cheapflights users on 10/6. 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 11/411:52 pm -
1 stop9h 33m
Sun 11/86:42 pm -
2 stops39h 37m
Deal found 10/6![Frontier logo]()
$275
This Cheapflightsfares deal was found by Cheapflights users on 10/5. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2311:59 pm -
1 stop12h 36m
Wed 10/286:16 am -
1 stop13h 54m
Deal found 10/5![Frontier logo]()
$276
This Kiwi.com deal was found by Cheapflights users on 10/5. 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 10/2611:59 pm -
1 stop9h 23m
Sat 11/77:15 am -
2 stops15h 17m
Deal found 10/5![Frontier logo]()
$277
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 October 9, 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 October 9, 2026.
This Southwest deal was found by Cheapflights users on 10/8. 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 12/182:15 pm -
1 stop7h 05m
Wed 12/237:35 am -
1 stop6h 45m
Deal found 10/8![Southwest logo]()
$310
This Delta deal was found by Cheapflights users on 10/8. 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 11/2411:35 pm -
1 stop7h 15m
Tue 12/15:30 pm -
1 stop8h 40m
Deal found 10/8![Delta logo]()
$442
This Southwest deal was found by Cheapflights users on 10/8. 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 11/511:35 pm -
Nonstop4h 25m
Tue 11/109:05 pm -
Nonstop4h 50m
Deal found 10/8![Southwest logo]()
$326
This Southwest deal was found by Cheapflights users on 10/7. 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 12/81:05 pm -
1 stop6h 50m
Wed 12/910:00 am -
Nonstop4h 50m
Deal found 10/7![Southwest logo]()
$340
This Southwest deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1311:35 pm -
Nonstop4h 25m
Sun 11/159:30 pm -
Nonstop4h 55m
Deal found 10/5![Southwest logo]()
$375
This Southwest deal was found by Cheapflights users on 10/4. 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 11/186:10 am -
2 stops8h 55m
Wed 11/2510:25 pm -
Nonstop4h 55m
Deal found 10/4![Southwest logo]()
$380
This Southwest deal was found by Cheapflights users on 10/5. 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 12/316:00 am -
Nonstop4h 15m
Mon 1/45:20 pm -
2 stops8h 00m
Deal found 10/5![Southwest logo]()
$388
This Southwest deal was found by Cheapflights users on 10/7. 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 11/59:05 am -
2 stops9h 30m
Thu 11/125:20 pm -
2 stops8h 05m
Deal found 10/7![Southwest logo]()
$413
This Southwest deal was found by Cheapflights users on 10/5. 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 10/249:20 am -
2 stops11h 00m
Tue 10/273:35 pm -
2 stops8h 05m
Deal found 10/5![Southwest logo]()
$413
This Southwest deal was found by Cheapflights users on 10/4. 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 10/296:10 am -
2 stops7h 20m
Thu 11/512:45 pm -
2 stops9h 25m
Deal found 10/4![Southwest logo]()
$414
Last-minute flights from San Francisco to MidwayDiscover last-minute flight deals from San Francisco to Midway. Data last updated October 9, 2026 and is based on user searches.
Discover last-minute flight deals from San Francisco to Midway. Data last updated October 9, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 10/5. 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 10/1311:59 pm -
1 stop12h 36m
Thu 10/151:12 pm -
1 stop11h 13m
Deal found 10/5![Frontier logo]()
$274
This Frontier deal was found by Cheapflights users on 10/5. 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 10/2011:59 pm -
1 stop12h 36m
Fri 11/612:20 pm -
1 stop12h 44m
Deal found 10/5![Frontier logo]()
$268
This Cheapflightsfares deal was found by Cheapflights users on 10/5. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2311:59 pm -
1 stop12h 36m
Wed 10/286:16 am -
1 stop13h 54m
Deal found 10/5![Frontier logo]()
$276
This Kiwi.com deal was found by Cheapflights users on 10/5. 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 10/2611:59 pm -
1 stop9h 23m
Fri 10/3012:20 pm -
1 stop12h 09m
Deal found 10/5![Frontier logo]()
$265
This Kiwi.com deal was found by Cheapflights users on 10/5. 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 10/2611:59 pm -
1 stop9h 23m
Sat 11/77:15 am -
2 stops15h 17m
Deal found 10/5![Frontier logo]()
$277
This Kiwi.com deal was found by Cheapflights users on 10/8. 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 10/277:14 pm -
2 stops14h 08m
Fri 10/3012:20 pm -
1 stop12h 09m
Deal found 10/8![Frontier logo]()
$273
This Southwest deal was found by Cheapflights users on 10/6. 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 10/286:50 pm -
2 stops8h 50m
Sat 10/3112:50 pm -
2 stops7h 25m
Deal found 10/6![Southwest logo]()
$262
This Southwest deal was found by Cheapflights users on 10/5. 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 10/2811:40 pm -
Nonstop4h 10m
Fri 10/309:25 pm -
Nonstop4h 45m
Deal found 10/5![Southwest logo]()
$272
This Southwest deal was found by Cheapflights users on 10/8. 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 10/296:00 am -
2 stops7h 10m
Sat 10/3112:50 pm -
2 stops7h 25m
Deal found 10/8![Southwest logo]()
$267
This Kiwi.com deal was found by Cheapflights users on 10/6. 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 11/411:52 pm -
1 stop9h 33m
Sun 11/86:42 pm -
2 stops39h 37m
Deal found 10/6![Frontier logo]()
$275
This Kiwi.com deal was found by Cheapflights users on 10/8. 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 11/139:09 am -
2 stops12h 38m
Sat 11/1412:20 pm -
1 stop12h 09m
Deal found 10/8![Frontier logo]()
$270
This Southwest deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1311:35 pm -
Nonstop4h 25m
Mon 11/169:05 pm -
Nonstop4h 50m
Deal found 10/7![Southwest logo]()
$271
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 October 9, 2026.
Search for one-way flight options from San Francisco to Midway. Find affordable one-way fares based on user searches. Data last updated October 9, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/6. 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 11/910:23 pm -
2 stops34h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Frontier logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 10/5. 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 11/1610:23 pm -
2 stops34h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Frontier logo]()
$124
This Trip.com deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/210:46 pm -
1 stop14h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Frontier logo]()
$125
This Delta deal was found by Cheapflights users on 10/8. 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 10/2610:55 pm -
1 stop8h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Delta logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 10/7. 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 10/2610:19 pm -
2 stops35h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Frontier logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/810:23 pm -
2 stops34h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Frontier logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 10/7. 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 12/36:30 pm -
2 stops18h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Frontier logo]()
$129
This Southwest deal was found by Cheapflights users on 10/6. 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 12/175:05 am -
2 stops7h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Southwest logo]()
$131
This Frontier deal was found by Cheapflights users on 10/5. 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 10/2011:59 pm -
1 stop12h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Frontier logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 10/6. 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 10/2910:23 pm -
2 stops35h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Frontier logo]()
$134
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 October 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $262 (Southwest) |
One-way from | $123 (Kiwi.com) |
Popular in | December |
Cheapest in | January |
Average price | $419 |
Good round-trip deal | $373 or less |
Good one-way deal | $219 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 7,457,451 searches. Data last updated October 9, 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 San Francisco - MDW Chicago Midway
SFOMDW
San Francisco
Thu 11/5
6:30 pm-4:25 am
1 stop7h 55m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$126
San FranciscoChicago
SFO San Francisco - MDW Chicago Midway
SFOMDW
San Francisco
Tue 10/27
6:05 am-4:47 pm
1 stop8h 42m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$126
San FranciscoChicago
SFO San Francisco - MDW Chicago Midway
SFOMDW
San Francisco
Wed 11/18
11:35 pm-8:50 am
1 stop7h 15m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$126
San FranciscoChicago
SFO San Francisco - MDW Chicago Midway
SFOMDW
San Francisco
Thu 10/29
2:40 pm-12:50 am
1 stop8h 10m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$126
San FranciscoChicago
SFO San Francisco - MDW Chicago Midway
SFOMDW
San Francisco
Mon 11/23
8:45 pm-5:55 am
1 stop7h 10m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$126
San FranciscoChicago
SFO San Francisco - MDW Chicago Midway
SFOMDW
San Francisco
Mon 10/26
10:55 pm-9:32 am
1 stop8h 37m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$126
San FranciscoChicago
SFO San Francisco - MDW Chicago Midway
SFOMDW
San Francisco
Wed 11/18
7:00 am-5:20 pm
2 stops8h 20m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$131
Quickest round-trip
San FranciscoChicago
SFO San Francisco - MDW Chicago Midway
SFOMDW
San Francisco
Fri 11/6
11:35 pm-6:00 am
Nonstop4h 25m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$156
San FranciscoChicago
SFO San Francisco - MDW Chicago Midway
SFOMDW
San Francisco
Fri 11/6
10:45 pm-9:32 am
1 stop8h 47m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$159
San FranciscoChicago
SFO San Francisco - MDW Chicago Midway
SFOMDW
San Francisco
Fri 12/4
9:20 pm-3:04 pm
2 stops15h 44m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$160
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 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 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 12 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 December is currently the most expensive (average of $493). 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 October 9, 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 October 9, 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.
Comfort
8.0
Overall
7.9
Food
7.0
Boarding
8.1
Entertainment
7.4
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Overall
7.9
Food
7.0
Boarding
8.1
Entertainment
7.4
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Overall
7.9
Food
7.0
Boarding
8.1
Entertainment
7.4
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Overall
7.9
Food
7.0
Boarding
8.1
Entertainment
7.4
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Overall
7.9
Food
7.0
Boarding
8.1
Entertainment
7.4
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Overall
7.9
Food
7.0
Boarding
8.1
Entertainment
7.4
Crew
8.6
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
Find flights from San Francisco to Midway, based on your preferred cabin class, be it economy, premium economy, business, or first class.
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 October 9, 2026.
San Francisco and Midway flights
Browse other San Francisco and Midway flight options. Last updated on October 9, 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 October 9, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 5 airlines flying from San Francisco to Midway
Discover the top 5 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 7,457,451 searches. Data last updated October 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$190 | Average$290 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$205 | Average$400 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$224 | Average$287 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$266 | Average$432 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$359 | Average$488 | FlexibilityNo cancel fee | On-time69% |