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$99+ 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 5/10. Fares are subject to change and may not be available on all flights or dates of travel.
SFO — MDW
Mar 1 — Mar 81
Sat 3/1
Sat 3/8
1 adult, Economy
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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 Tuesday and return on a Tuesday

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 February 24, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$202
(Trip.com)

One-way from

$99
(Southwest)

Popular in

December

Cheapest in

September

Average price

$247

Good round-trip deal

$338 or less

Good one-way deal

$218 or less
Provider with most accurate pricing for San Francisco-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for San Francisco-Chicago Midway flights.
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From San Francisco to Chicago Midway
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One-way flight from San Francisco to Chicago Midway
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Highest demand for flights based on searches. 11% potential increase in price ($34 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 24, 2025.

This Trip.com deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/148:04 pmSFO - MDW
1 stop7h 27mFrontier
Wed 3/196:40 amMDW - SFO
1 stop8h 53mFrontier
Deal found 2/23$202
This Southwest deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/206:10 amSFO - MDW
Nonstop4h 10mSouthwest
Mon 3/316:20 pmMDW - SFO
Nonstop4h 40mSouthwest
Deal found 2/23$217
This Delta deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1112:30 amSFO - MDW
1 stop8h 12mDelta
Mon 4/147:00 pmMDW - SFO
1 stop6h 59mDelta
Deal found 2/23$257

Find flights from San Francisco to Midway within your budget

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 February 24, 2025.

Fly from

San Francisco

Fly to

Midway

Route

Depart

Return

Price

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Fri 3/14

8:04 pm-5:31 am

1 stop7h 27m

Chicago Midway

Wed 3/19

6:40 am-1:33 pm

1 stop8h 53m

$202

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Thu 3/20

6:10 am-12:20 pm

Nonstop4h 10m

Chicago Midway

Mon 3/31

6:20 pm-9:00 pm

Nonstop4h 40m

$217

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Fri 4/11

12:30 am-10:42 am

1 stop8h 12m

Chicago Midway

Sat 4/19

1:16 pm-8:37 pm

1 stop9h 21m

$257

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Sat 5/10

6:45 am-12:55 pm

Nonstop4h 10m

$99

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Thu 5/8

7:02 pm-10:09 am

1 stop13h 07m

$101

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Sun 3/9

8:19 pm-5:31 am

1 stop7h 12m

$104

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Fri 5/2

12:47 am-9:40 am

1 stop6h 53m

$129

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/24

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 February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightnetworkPrice Accuracy-Trust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*3 stars
Justfly.comPrice Accuracy3 starsTrust Score*3 stars
MytripPrice Accuracy3 starsTrust Score*3 stars
CheapOairPrice Accuracy1 starTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*2 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • 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.
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.

Travel insights for flights from San Francisco to Midway

Get recent, data-driven insights about flights from San Francisco to Midway including ideal travel times, pricing trends, and more.

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 February 14, 2025.

The best time to book flights from San Francisco to Chicago Midway Airport is 87 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 February 24, 2025.

It’s typically best to fly out from San Francisco to Chicago Midway Airport in the afternoon. Doing so could potentially save you 65% 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 February 16, 2025.

Travelers seeking maximum savings on their San Francisco to Chicago Midway Airport flight should consider departing on Wednesday 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.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 February 24, 2025.
Read reviews from past customers who have flown Southwest, Delta and Frontier from San Francisco to Chicago. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,380 reviews

Food

7.1

Entertainment

7.6

Crew

8.7

Boarding

8.2

Comfort

8.1

Overall

8.1

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
8.1
Very good
4,380 reviews
Southwest
8.1
Very good
4,380 reviews

Food

7.1

Entertainment

7.6

Crew

8.7

Boarding

8.2

Comfort

8.1

Overall

8.1

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
8,175 reviews
Southwest
8.1
Very good
4,380 reviews

Food

7.1

Entertainment

7.6

Crew

8.7

Boarding

8.2

Comfort

8.1

Overall

8.1

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
6.0
Okay
3,344 reviews
Southwest
8.1
Very good
4,380 reviews

Food

7.1

Entertainment

7.6

Crew

8.7

Boarding

8.2

Comfort

8.1

Overall

8.1

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. 5 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 1 outbound flight 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 $202. Other airlines that can offer you cheap pricing are Southwest, from $207, and Delta, from $253. These flights start at 26% 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 Southwest, which is currently one of the cheapest options available, starting at $99. Frontier flights start at $104 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 $345 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 $150.

  • 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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 2,558,603 searches. Data last updated February 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$74Average$242FlexibilityNo cancel feeOn-time62%
Alaska AirlinesCheapest$168Average$292FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$185Average$338FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$208Average$410FlexibilityNo cancel feeOn-time63%
DeltaCheapest$236Average$415FlexibilityNo cancel feeOn-timeN/A
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