$133+ 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 5/27. Fares are subject to change and may not be available on all flights or dates of travel.
SFO — MDW
Jun 13 — Jun 201
Round-trip
1 adult, Economy
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Find cheap flights from San Francisco to Midway with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from San Francisco to Chicago Midway are usually found in January or 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 May 14, 2026.
Explore the most affordable flight options available from San Francisco to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 14, 2026.
This Frontier deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/2510:15 pm
SFO
- MDW
1 stop10h 57m
Frontier
Sat 5/306:00 am
MDW
- SFO
1 stop15h 34m
Frontier
Deal found 5/10![Frontier logo]()
$290
This Southwest deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/110:55 pm
SFO
- MDW
1 stop7h 30m
Southwest
Tue 6/95:05 am
MDW
- SFO
1 stop6h 40m
Southwest
Deal found 5/9![Southwest logo]()
$292
This Kissandfly.com deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/110:05 pm
SFO
- MDW
1 stop11h 07m
Frontier
Tue 6/91:49 pm
MDW
- SFO
1 stop9h 11m
Frontier
Deal found 5/11![Frontier logo]()
$294
This Southwest deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/145:15 am
SFO
- MDW
Nonstop4h 10m
Southwest
Wed 7/299:30 pm
MDW
- SFO
Nonstop4h 40m
Southwest
Deal found 5/9![Southwest logo]()
$296
This Frontier deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2810:15 pm
SFO
- MDW
1 stop10h 54m
Frontier
Wed 6/33:07 pm
MDW
- SFO
1 stop9h 57m
Frontier
Deal found 5/12![Frontier logo]()
$300
This Trip.com deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/3111:59 pm
SFO
- MDW
1 stop12h 13m
Frontier
Sat 8/16:00 am
MDW
- SFO
1 stop15h 13m
Frontier
Deal found 5/11![Frontier logo]()
$301
This Trip.com deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/210:10 pm
SFO
- MDW
1 stop10h 59m
Frontier
Sun 7/53:22 pm
MDW
- SFO
1 stop9h 32m
Frontier
Deal found 5/12![Frontier logo]()
$302
This Southwest deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/32:50 pm
SFO
- MDW
1 stop12h 10m
Southwest
Thu 6/49:30 pm
MDW
- SFO
Nonstop4h 40m
Southwest
Deal found 5/11![Southwest logo]()
$303
This Southwest deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/145:35 am
SFO
- MDW
Nonstop4h 05m
Southwest
Tue 8/188:30 pm
MDW
- SFO
Nonstop4h 35m
Southwest
Deal found 5/12![Southwest logo]()
$305
This Southwest deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/153:10 pm
SFO
- MDW
1 stop6h 55m
Southwest
Tue 7/219:30 pm
MDW
- SFO
Nonstop4h 40m
Southwest
Deal found 5/13![Southwest logo]()
$306
This Southwest deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/110:55 pm
SFO
- MDW
1 stop7h 30m
Southwest
Mon 6/86:00 pm
MDW
- SFO
1 stop6h 25m
Southwest
Deal found 5/9![Southwest logo]()
$307
Best flights from San Francisco to MidwayDiscover carefully curated flight deals from San Francisco to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 14, 2026.
Discover carefully curated flight deals from San Francisco to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 14, 2026.
This Delta deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/810:55 pm
SFO
- MDW
1 stop8h 19m
Delta
Tue 6/161:26 pm
MDW
- SFO
1 stop6h 47m
Delta
Deal found 5/13![Delta logo]()
$318
This Southwest deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/111:40 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Tue 8/118:30 pm
MDW
- SFO
Nonstop4h 35m
Southwest
Deal found 5/13![Southwest logo]()
$332
This Southwest deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/82:15 pm
SFO
- MDW
2 stops7h 55m
Southwest
Tue 6/95:05 am
MDW
- SFO
1 stop6h 40m
Southwest
Deal found 5/13![Southwest logo]()
$339
This Southwest deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/111:40 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Wed 7/86:00 am
MDW
- SFO
1 stop9h 40m
Southwest
Deal found 5/10![Southwest logo]()
$342
This Southwest deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/172:00 pm
SFO
- MDW
1 stop7h 25m
Southwest
Mon 7/209:30 pm
MDW
- SFO
Nonstop4h 40m
Southwest
Deal found 5/9![Southwest logo]()
$354
This Southwest deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/2411:40 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Tue 7/289:30 pm
MDW
- SFO
Nonstop4h 40m
Southwest
Deal found 5/13![Southwest logo]()
$362
This Southwest deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/106:00 am
SFO
- MDW
2 stops8h 55m
Southwest
Fri 6/129:30 pm
MDW
- SFO
Nonstop4h 40m
Southwest
Deal found 5/13![Southwest logo]()
$368
This Southwest deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/166:00 am
SFO
- MDW
2 stops8h 55m
Southwest
Mon 6/228:15 pm
MDW
- SFO
1 stop6h 15m
Southwest
Deal found 5/10![Southwest logo]()
$369
This Southwest deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/1211:40 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Sat 6/138:50 pm
MDW
- SFO
Nonstop4h 40m
Southwest
Deal found 5/9![Southwest logo]()
$371
This Southwest deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1011:40 pm
SFO
- MDW
Nonstop4h 10m
Southwest
Sun 8/169:20 pm
MDW
- SFO
Nonstop4h 35m
Southwest
Deal found 5/11![Southwest logo]()
$371
This Southwest deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/92:00 pm
SFO
- MDW
2 stops8h 35m
Southwest
Tue 7/145:50 pm
MDW
- SFO
2 stops7h 25m
Southwest
Deal found 5/13![Southwest logo]()
$375
This Southwest deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/1611:40 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Fri 6/199:30 pm
MDW
- SFO
Nonstop4h 40m
Southwest
Deal found 5/9![Southwest logo]()
$380
Last-minute flights from San Francisco to MidwayDiscover last-minute flight deals from San Francisco to Midway. Data last updated May 14, 2026 and is based on user searches.
Discover last-minute flight deals from San Francisco to Midway. Data last updated May 14, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/2510:15 pm
SFO
- MDW
1 stop10h 57m
Frontier
Sat 5/306:00 am
MDW
- SFO
1 stop15h 34m
Frontier
Deal found 5/10![Frontier logo]()
$290
This Expedia deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2710:15 pm
SFO
- MDW
1 stop10h 57m
Frontier
Sat 5/3011:59 am
MDW
- SFO
1 stop9h 35m
Frontier
Deal found 5/13![Frontier logo]()
$305
This Frontier deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2810:15 pm
SFO
- MDW
1 stop10h 54m
Frontier
Wed 6/33:07 pm
MDW
- SFO
1 stop9h 57m
Frontier
Deal found 5/12![Frontier logo]()
$300
This Super.com deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2811:59 pm
SFO
- MDW
1 stop12h 13m
Frontier
Wed 8/512:11 pm
MDW
- SFO
1 stop9h 02m
Frontier
Deal found 5/13![Frontier logo]()
$308
This Frontier deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2910:15 pm
SFO
- MDW
1 stop10h 49m
Frontier
Sat 8/83:22 pm
MDW
- SFO
1 stop9h 32m
Frontier
Deal found 5/13![Frontier logo]()
$310
This Trip.com deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/3111:59 pm
SFO
- MDW
1 stop12h 13m
Frontier
Sat 8/16:00 am
MDW
- SFO
1 stop15h 13m
Frontier
Deal found 5/11![Frontier logo]()
$301
This Southwest deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/110:55 pm
SFO
- MDW
1 stop7h 30m
Southwest
Tue 6/95:05 am
MDW
- SFO
1 stop6h 40m
Southwest
Deal found 5/9![Southwest logo]()
$292
This Kissandfly.com deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/110:05 pm
SFO
- MDW
1 stop11h 07m
Frontier
Tue 6/91:49 pm
MDW
- SFO
1 stop9h 11m
Frontier
Deal found 5/11![Frontier logo]()
$294
This Southwest deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/32:50 pm
SFO
- MDW
1 stop12h 10m
Southwest
Thu 6/49:30 pm
MDW
- SFO
Nonstop4h 40m
Southwest
Deal found 5/11![Southwest logo]()
$303
This Southwest deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/95:15 am
SFO
- MDW
Nonstop4h 10m
Southwest
Tue 6/165:35 am
MDW
- SFO
1 stop7h 50m
Southwest
Deal found 5/12![Southwest logo]()
$306
One-way flights from San Francisco to MidwaySearch for one-way flight options from San Francisco to Midway. Find affordable one-way fares based on user searches. Data last updated May 14, 2026.
Search for one-way flight options from San Francisco to Midway. Find affordable one-way fares based on user searches. Data last updated May 14, 2026.
This Trip.com deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2710:15 pm
SFO
- MDW
1 stop10h 57m
Frontier
Deal found 5/10![Frontier logo]()
$133
This Trip.com deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/3010:10 pm
SFO
- MDW
1 stop10h 57m
Frontier
Deal found 5/9![Frontier logo]()
$134
This Frontier deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/2610:15 pm
SFO
- MDW
1 stop10h 54m
Frontier
Deal found 5/10![Frontier logo]()
$135
This Delta deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/612:35 am
SFO
- MDW
1 stop6h 02m
Delta
Deal found 5/13![Delta logo]()
$139
This Frontier deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/110:05 pm
SFO
- MDW
1 stop11h 07m
Frontier
Deal found 5/12![Frontier logo]()
$141
This Southwest deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/811:40 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Deal found 5/13![Southwest logo]()
$144
This Frontier deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2410:15 pm
SFO
- MDW
1 stop10h 57m
Frontier
Deal found 5/12![Frontier logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1710:56 pm
SFO
- MDW
2 stops45h 15m
Frontier
Deal found 5/13![Frontier logo]()
$147
This Super.com deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2810:15 pm
SFO
- MDW
1 stop10h 54m
Frontier
Deal found 5/11![Frontier logo]()
$148
This Super.com deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/2410:10 pm
SFO
- MDW
1 stop10h 57m
Frontier
Deal found 5/10![Frontier logo]()
$149
This Super.com deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/2612:24 am
SFO
- MDW
1 stop12h 03m
Frontier
Deal found 5/13![Frontier logo]()
$150
Find flight deals from San Francisco to Midway
Discover tips and strategies to find the most affordable flight options for your journey from San Francisco (SFO) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated May 14, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $290 (Frontier) |
One-way from | $133 (Trip.com) |
Popular in | December |
Cheapest in | January |
Average price | $359 |
Good round-trip deal | $385 or less |
Good one-way deal | $205 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from San Francisco to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 14, 2026.
Use the filters below to find and compare flights from San Francisco to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Mon 6/8
10:55 pm-9:14 am
1 stop8h 19m
Chicago Midway
Tue 6/16
1:26 pm-6:13 pm
1 stop6h 47m
$318
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Sat 8/1
11:40 pm-5:55 am
Nonstop4h 15m
Chicago Midway
Tue 8/11
8:30 pm-11:05 pm
Nonstop4h 35m
$332
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Mon 6/8
2:15 pm-12:10 am
2 stops7h 55m
Chicago Midway
Tue 6/9
5:05 am-9:45 am
1 stop6h 40m
$339
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Wed 7/1
11:40 pm-5:55 am
Nonstop4h 15m
Chicago Midway
Wed 7/8
6:00 am-1:40 pm
1 stop9h 40m
$342
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Fri 7/17
2:00 pm-11:25 pm
1 stop7h 25m
Chicago Midway
Mon 7/20
9:30 pm-12:10 am
Nonstop4h 40m
$354
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Fri 7/24
11:40 pm-5:55 am
Nonstop4h 15m
Chicago Midway
Tue 7/28
9:30 pm-12:10 am
Nonstop4h 40m
$362
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Wed 6/10
6:00 am-4:55 pm
2 stops8h 55m
Chicago Midway
Fri 6/12
9:30 pm-12:10 am
Nonstop4h 40m
$368
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Tue 6/16
6:00 am-4:55 pm
2 stops8h 55m
Chicago Midway
Mon 6/22
8:15 pm-12:30 am
1 stop6h 15m
$369
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Fri 6/12
11:40 pm-5:55 am
Nonstop4h 15m
Chicago Midway
Sat 6/13
8:50 pm-11:30 pm
Nonstop4h 40m
$371
Quickest round-trip
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Mon 8/10
11:40 pm-5:50 am
Nonstop4h 10m
Chicago Midway
Sun 8/16
9:20 pm-11:55 pm
Nonstop4h 35m
$371
Showing 1-10 of 23 resultsSorted by cheapest first
Compare providers for flights from San Francisco to Midway
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from San Francisco to Midway in May.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on San Francisco-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on San Francisco-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from San Francisco-Chicago Midway Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on San Francisco-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for San Francisco-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from San Francisco to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from San Francisco with our price prediction graph.
SFO-MDW
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from San Francisco to Chicago Midway Airport
Prices
Airlines
How far ahead should I book a flight from San Francisco to Chicago Midway Airport?
The best time to book flights from San Francisco to Chicago Midway Airport is 83 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest month to book a flight from San Francisco to Chicago Midway Airport?
Currently, January is the cheapest month in which you can book a flight from San Francisco to Chicago Midway Airport (average of $225). Flying from San Francisco to Chicago Midway Airport in December is currently the most expensive (average of $442). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from SFO to MDW?
Find hourly flight availability from San Francisco to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 14, 2026.
It’s typically best to fly out from San Francisco to Chicago Midway Airport in the afternoon. Doing so could potentially save you 37% on the flight price compared to flying at noon, which is usually more expensive.
Reviews of airlines servicing Midway
Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated May 14, 2026.
Read through reviews of airlines operating flights from San Francisco to Chicago Midway Airport, such as Southwest,Delta, andUnited Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Overall
8.0
Food
7.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Boarding
8.1
Overall
8.0
Food
7.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Boarding
8.1
Overall
8.0
Food
7.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Boarding
8.1
Overall
8.0
Food
7.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Boarding
8.1
Overall
8.0
Food
7.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Related info for your journey
Find useful and relevant information for your journey from San Francisco to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Hammond
Porter
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Search flights from San Francisco to Midway by cabin class
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Other flights to Midway
Explore flights to Midway departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on May 14, 2026.
San Francisco and Midway flights
Browse other San Francisco and Midway flight options. Last updated on May 14, 2026.
Other flights from San Francisco
Browse through other flights departing from San Francisco. Flights are based on user searches made on Cheapflights and were last updated on May 14, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 4 airlines flying from San Francisco to Midway
Discover the top 4 airlines that operate flights from San Francisco to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 14, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$133 | Average$456 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$147 | Average$267 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$225 | Average$421 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$250 | Average$421 | FlexibilityNo cancel fee | On-time63% |