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$103+ 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 9/29. Fares are subject to change and may not be available on all flights or dates of travel.
SFO — MDW
Jul 6 — Jul 131
Sun 7/6
Sun 7/13
1 adult, Economy
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Cheapflights Tip: The best prices from San Francisco to Chicago Midway are usually found in September or January, booked 87 days in advance, depart on a Wednesday or Friday and return on a Wednesday

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 July 1, 2025.

Round-trip from

$207
(Southwest)

One-way from

$103
(Frontier)

Popular in

December

Cheapest in

September

Average price

$329

Good round-trip deal

$323 or less

Good one-way deal

$169 or less
From San Francisco to Chicago Midway
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One-way flight from San Francisco to Chicago Midway
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High demand for flights, 0% potential price rise
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Cheapest flight prices on average. 4% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Price to beat on a round-trip flight from San Francisco to Chicago Midway.
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Price to beat on a one-way flight from San Francisco to Chicago Midway.
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Find flight deals from San Francisco to Midway

Cheapest flights from San Francisco to Midway
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 July 1, 2025.

This Southwest deal was found by Cheapflights users on 6/30. 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 8/127:50 amSFO - MDW
1 stop8h 40mSouthwest
Tue 8/193:50 pmMDW - SFO
Nonstop4h 35mSouthwest
Deal found 6/30$207
This Priceline deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/45:45 amSFO - MDW
1 stop7h 11mFrontier
Sat 7/192:44 pmMDW - SFO
1 stop10h 41mFrontier
Deal found 6/28$208
This Delta deal was found by Cheapflights users on 6/30. 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 8/1812:40 amSFO - MDW
1 stop6h 11mDelta
Sun 8/247:17 pmMDW - SFO
1 stop6h 40mDelta
Deal found 6/30$257

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 July 1, 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

Tue 8/12

7:50 am-6:30 pm

1 stop8h 40m

Chicago Midway

Tue 8/19

3:50 pm-6:25 pm

Nonstop4h 35m

$207

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Fri 7/4

5:45 am-2:56 pm

1 stop7h 11m

Chicago Midway

Sat 7/19

2:44 pm-11:25 pm

1 stop10h 41m

$208

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Mon 8/18

12:40 am-8:51 am

1 stop6h 11m

Chicago Midway

Sun 8/24

7:17 pm-11:57 pm

1 stop6h 40m

$257

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Mon 9/29

6:29 am-3:53 pm

1 stop7h 24m

$103

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Mon 8/25

7:15 am-1:20 pm

Nonstop4h 05m

$109

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Tue 7/29

12:50 am-8:45 am

1 stop5h 55m

$129

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/30

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 June 27, 2025.

The best time to book flights from San Francisco to Chicago Midway Airport is 86 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 July 1, 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 June 29, 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 July 1, 2025.
Read through reviews of airlines operating flights from San Francisco to Chicago Midway Airport, such as Southwest, Delta, and Frontier. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,273 reviews

Boarding

8.2

Entertainment

7.6

Food

7.0

Crew

8.6

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Southwest
8.0
Very good
4,273 reviews
Southwest
8.0
Very good
4,273 reviews

Boarding

8.2

Entertainment

7.6

Food

7.0

Crew

8.6

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Delta
8.0
Very good
7,973 reviews
Southwest
8.0
Very good
4,273 reviews

Boarding

8.2

Entertainment

7.6

Food

7.0

Crew

8.6

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Frontier
5.9
Fair
3,291 reviews
Southwest
8.0
Very good
4,273 reviews

Boarding

8.2

Entertainment

7.6

Food

7.0

Crew

8.6

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

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.

  • What airport do you fly from for flights from San Francisco to Chicago Midway?

    San Francisco (SFO), located 11.8 mi from the city center, is the airport you fly out of when you book flights from San Francisco to Chicago Midway. 6 airlines have flights from San Francisco to Chicago Midway on a regular basis. Booking flights from San Francisco to Chicago Midway should not be difficult; the airport handles an average of 0 outbound flights to Chicago Midway per day.

  • What are the cheapest airlines flying from San Francisco to Chicago Midway Airport round-trip?

    Cheapflights users have booked flights from San Francisco to Chicago Midway Airport round-trip from $207. Other airlines that can offer you cheap pricing are Frontier, from $209, and Delta, from $257. These flights start at 34% lower than the current average price 3 months from now.

  • What are the cheapest airlines to fly from San Francisco to Chicago Midway Airport one-way?

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $103. Southwest flights start at $109 while deals on Delta start at $129 one-way.

  • What are the cheapest flights from San Francisco to Chicago Midway Airport?

    On average you can expect to pay $336 for a flight from San Francisco to Chicago Midway Airport. The cheapest flight overall is $108 while the most popular route, (San Francisco - Chicago Midway) is currently priced at $197.

  • Can I find deals for flights from San Francisco to Midway that include hotel bookings?

    Yes. In addition to deals on San Francisco to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from San Francisco to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from San Francisco to Midway.

  • Can I find deals for business class flights from San Francisco to Midway?

    Yes. Cheapflights offers flight deals from San Francisco to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • 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.

See more FAQs

Traveling to a place near San Francisco?

Book flights to San Francisco if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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Alternative routes for San Francisco to Midway

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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 July 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$60Average$221FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$133Average$287FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$197Average$332FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$197Average$280FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$210Average$400FlexibilityNo cancel feeOn-time63%
DeltaCheapest$236Average$337FlexibilityNo cancel feeOn-timeN/A

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