$101+ 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 10/20. Fares are subject to change and may not be available on all flights or dates of travel.
SFO — MDW
Oct 11 — Oct 181
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 February, booked 66 days in advance, depart on a Wednesday or Thursday and return on a Thursday
Cheap 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 September 11, 2025.
Round-trip from | $207 (CheapOair) |
|---|---|
One-way from | $101 (Kiwi.com) |
Popular in | December |
Cheapest in | January |
Average price | $371 |
Good round-trip deal | $316 or less |
Good one-way deal | $208 or less |
Find flight deals from San Francisco to Midway
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 September 11, 2025.
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 September 11, 2025.
This CheapOair deal was found by Cheapflights users on 9/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/136:33 pmSFO - MDW
2 stops14h 57mFrontier
Sun 11/1612:30 pmMDW - SFO
1 stop28h 10mFrontier
Deal found 9/11![Frontier logo]()
$207
This CheapOair deal was found by Cheapflights users on 9/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/27:07 pmSFO - MDW
1 stop18h 46mFrontier
Mon 10/67:15 amMDW - SFO
1 stop17h 47mFrontier
Deal found 9/10![Frontier logo]()
$208
This Southwest deal was found by Cheapflights users on 9/10. 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.
Sat 10/255:00 amSFO - MDW
2 stops9h 25mSouthwest
Tue 10/282:45 pmMDW - SFO
1 stop7h 05mSouthwest
Deal found 9/10![Southwest logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/265:45 amSFO - MDW
1 stop13h 07mMultiple Airlines
Mon 9/297:03 pmMDW - SFO
1 stop28h 18mMultiple Airlines
Deal found 9/9![Multiple Airlines logo]()
$210
This CheapOair deal was found by Cheapflights users on 9/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2511:57 pmSFO - MDW
1 stop18h 55mFrontier
Mon 9/299:47 pmMDW - SFO
2 stops49h 34mFrontier
Deal found 9/10![Frontier logo]()
$211
This CheapOair deal was found by Cheapflights users on 9/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/311:57 pmSFO - MDW
1 stop8h 31mFrontier
Mon 10/67:15 amMDW - SFO
1 stop17h 47mFrontier
Deal found 9/10![Frontier logo]()
$212
This Southwest deal was found by Cheapflights users on 9/9. 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 10/71:05 pmSFO - MDW
1 stop8h 30mSouthwest
Tue 10/145:30 pmMDW - SFO
2 stops7h 35mSouthwest
Deal found 9/9![Southwest logo]()
$213
This CheapOair deal was found by Cheapflights users on 9/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2410:43 pmSFO - MDW
2 stops22h 37mFrontier
Mon 10/275:10 amMDW - SFO
1 stop12h 50mFrontier
Deal found 9/10![Frontier logo]()
$214
This Southwest deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/196:00 amSFO - MDW
Nonstop4h 05mSouthwest
Sat 10/258:20 amMDW - SFO
2 stops11h 15mSouthwest
Deal found 9/10![Southwest logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/78:00 amSFO - MDW
2 stops13h 20mMultiple Airlines
Thu 10/166:24 pmMDW - SFO
1 stop7h 50mMultiple Airlines
Deal found 9/11![Multiple Airlines logo]()
$216
This Southwest deal was found by Cheapflights users on 9/8. 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.
Sat 10/187:00 amSFO - MDW
1 stop6h 10mSouthwest
Sat 10/258:30 amMDW - SFO
2 stops9h 15mSouthwest
Deal found 9/8![Southwest logo]()
$217
This CheapOair deal was found by Cheapflights users on 9/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2211:00 pmSFO - MDW
1 stop14h 58mFrontier
Fri 9/266:20 amMDW - SFO
1 stop17h 01mFrontier
Deal found 9/11![Frontier logo]()
$218
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 September 11, 2025.
Use the filters below to find and compare flights from San Francisco to Chicago Midway Airport that are best for you.
Fly from
San Francisco
Fly to
Midway
Route
Depart
Return
Price
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Sun 10/19
6:00 am-12:05 pm
Nonstop4h 05m
Chicago Midway
Fri 10/24
6:25 pm-12:05 am
1 stop7h 40m
$207
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Mon 10/20
6:00 am-12:05 pm
Nonstop4h 05m
Chicago Midway
Tue 10/28
2:45 pm-5:15 pm
Nonstop4h 30m
$251
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Sat 10/25
5:00 am-4:25 pm
2 stops9h 25m
Chicago Midway
Tue 10/28
10:20 am-5:05 pm
2 stops8h 45m
$255
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Sat 10/4
11:00 pm-8:40 am
1 stop7h 40m
Chicago Midway
Sat 10/11
3:00 pm-8:40 pm
1 stop7h 40m
$257
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Wed 11/5
10:57 pm-8:40 am
1 stop7h 43m
Chicago Midway
Sat 11/8
3:00 pm-8:40 pm
1 stop7h 40m
$257
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Sat 10/25
6:10 am-3:26 pm
1 stop7h 16m
Chicago Midway
Tue 10/28
9:35 am-2:13 pm
1 stop6h 38m
$257
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Sun 10/19
6:00 am-12:05 pm
Nonstop4h 05m
Chicago Midway
Wed 10/22
2:45 pm-5:15 pm
Nonstop4h 30m
$257
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Wed 11/12
6:10 am-12:15 pm
Nonstop4h 05m
Chicago Midway
Sun 11/16
8:20 am-11:05 am
Nonstop4h 45m
$259
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Wed 10/1
5:55 am-1:45 pm
1 stop5h 50m
Chicago Midway
Mon 10/6
5:05 am-11:05 am
1 stop8h 00m
$268
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Sat 10/4
6:20 pm-5:00 am
1 stop8h 40m
$106
Showing 1-10 of 20 results
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.
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
How far ahead should I book a flight from San Francisco to Chicago Midway Airport?
Use this chart to determine the optimal time to book a round-trip flight from San Francisco to Midway. Price data was last updated on August 29, 2025.
The best time to book flights from San Francisco to Chicago Midway Airport is 65 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, April is the cheapest month in which you can book a flight from San Francisco to Chicago Midway Airport (average of $160). Flying from San Francisco to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 September 11, 2025.
It’s typically best to fly out from San Francisco to Chicago Midway Airport in the evening. Doing so could potentially save you 47% on the flight price compared to flying at noon, which is usually more expensive.
What is the cheapest day to fly from San Francisco to Chicago Midway Airport?
Use this chart to determine the cheapest time to fly round-trip from San Francisco to Midway. Price data was last updated on September 7, 2025.
Travelers seeking maximum savings on their San Francisco to Chicago Midway Airport flight should consider departing on Friday afternoons when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
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 September 11, 2025.
Read through reviews of airlines operating flights from San Francisco to Chicago Midway Airport, such as Southwest, Delta, and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Overall
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentWalter,Aug 2025
OAK - SAN
Comfort
8.0
Overall
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentWalter,Aug 2025
OAK - SAN
Comfort
8.0
Overall
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentWalter,Aug 2025
OAK - SAN
Comfort
8.0
Overall
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentWalter,Aug 2025
OAK - SAN
Comfort
8.0
Overall
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentWalter,Aug 2025
OAK - SAN
Comfort
8.0
Overall
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentWalter,Aug 2025
OAK - SAN
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 locationsMerrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton
Browse thousands of different options on Cheapflights for your next trip
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Alternative routes for San Francisco to Midway
See prices for flight routes from nearby airports that may be better suited for you.
Top 6 airlines flying from San Francisco to Midway
Discover the top 6 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 September 11, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$133 | Average$307 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$138 | Average$239 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$197 | Average$332 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$197 | Average$280 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$216 | Average$397 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$256 | Average$357 | FlexibilityNo cancel fee | On-timeN/A |