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$108+ Cheap flights from Midway (MDW) to San Francisco (SFO)

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.
MDW — SFO
Aug 2 — Aug 91
Sat 8/2
Sat 8/9
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago Midway to San Francisco are usually found in August or November, booked 83 days in advance, depart on a Wednesday or Saturday and return on a Friday

Cheap flight deals from Midway to San Francisco

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to San Francisco (SFO). 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 28, 2025.

Round-trip from

$207
(Southwest)

One-way from

$108
(Trip.com)

Popular in

December

Cheapest in

August

Average price

$371

Good round-trip deal

$207 or less

Good one-way deal

$108 or less
From Chicago Midway to San Francisco
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One-way flight from Chicago Midway to San Francisco
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Highest demand for flights based on searches. 3% potential increase in price ($15 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 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 Chicago Midway to San Francisco.
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Price to beat on a one-way flight from Chicago Midway to San Francisco.
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Find flight deals from Midway to San Francisco

Cheapest flights from Midway to San Francisco
Explore the most affordable flight options available from Midway to San Francisco. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 28, 2025.

This Southwest deal was found by Cheapflights users on 7/26. 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 8/263:50 pmMDW - SFO
Nonstop4h 35mSouthwest
Wed 8/2711:25 amSFO - MDW
1 stop9h 00mSouthwest
Deal found 7/26$207
This Frontier deal was found by Cheapflights users on 7/27. 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.
Sat 8/162:44 pmMDW - SFO
1 stop10h 41mFrontier
Sat 8/2310:29 pmSFO - MDW
1 stop9h 39mFrontier
Deal found 7/27$238
This Delta deal was found by Cheapflights users on 7/27. 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.
Sat 9/201:08 pmMDW - SFO
1 stop6h 39mDelta
Wed 9/246:15 amSFO - MDW
1 stop9h 20mDelta
Deal found 7/27$257

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to San Francisco 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 28, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to San Francisco that are best for you.

Fly from

Midway

Fly to

San Francisco

Route

Depart

Return

Price

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Tue 8/26

3:50 pm-6:25 pm

Nonstop4h 35m

San Francisco

Wed 8/27

11:25 am-10:25 pm

1 stop9h 00m

$207

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Sat 8/16

2:44 pm-11:25 pm

1 stop10h 41m

San Francisco

Sat 8/23

10:29 pm-10:08 am

1 stop9h 39m

$238

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Sat 9/20

11:00 am-6:48 pm

1 stop9h 48m

San Francisco

Tue 9/23

12:45 am-8:53 am

1 stop6h 08m

$257

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Mon 10/20

4:29 pm-12:14 am

1 stop9h 45m

$108

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Tue 8/19

6:00 am-10:05 am

1 stop6h 05m

$109

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Mon 8/18

1:43 pm-9:29 pm

1 stop9h 46m

$129

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

Mon 8/18

12:35 pm-10:10 am

2 stops23h 35m

$179

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

Best time to book a flight from Midway to San Francisco

Have a flexible travel schedule? Discover the best time to fly to San Francisco from Midway 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 Chicago Midway Airport to San Francisco

How far ahead should I book a flight from Chicago Midway Airport to San Francisco?

Use this chart to determine the optimal time to book a round-trip flight from Midway to San Francisco. Price data was last updated on July 25, 2025.

The best time to book flights from Chicago Midway Airport to San Francisco is 80 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 Chicago Midway Airport to San Francisco?

Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to San Francisco (average of $276). Flying from Chicago Midway Airport to San Francisco in June is currently the most expensive (average of $358). 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 MDW to SFO?

Find hourly flight availability from Midway to San Francisco. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 28, 2025.

It’s typically best to fly out from Chicago Midway Airport to San Francisco in the afternoon. Doing so could potentially save you 36% on the flight price compared to flying at noon, which is usually more expensive.

What is the cheapest day to fly from Chicago Midway Airport to San Francisco?

Use this chart to determine the cheapest time to fly round-trip from Midway to San Francisco. Price data was last updated on July 27, 2025.

Travelers seeking maximum savings on their Chicago Midway Airport to San Francisco flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Friday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing San Francisco

Get insights into the airlines that provide service to San Francisco. 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 San Francisco. Reviews last updated July 28, 2025.
Read reviews from past customers who have flown Southwest, Delta, and Frontier from Chicago Midway Airport to San Francisco. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,237 reviews

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Crew

8.6

Overall

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
4,237 reviews
Southwest
8.0
Very good
4,237 reviews

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Crew

8.6

Overall

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
7,971 reviews
Southwest
8.0
Very good
4,237 reviews

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Crew

8.6

Overall

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
3,238 reviews
Southwest
8.0
Very good
4,237 reviews

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Crew

8.6

Overall

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 Midway to San Francisco. 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 into for flights to San Francisco from Chicago Midway?

    Located just 11.8 mi from the city center, San Francisco is the airport most travelers will use when flying to San Francisco from Chicago Midway. Booking flights from Chicago Midway to San Francisco (SFO) should be relatively easy as there are 0 daily inbound flights from Chicago Midway from 3 different airlines.

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

    According to our current data, Southwest ($207), Frontier ($238), and Delta ($257) offers the cheapest pricing from Chicago Midway Airport to San Francisco. You may be able to fly from Chicago Midway Airport to San Francisco for 44% less than the average price by searching for these airlines.

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

    The cheapest airline one-way is Frontier, with whom users have recently found tickets for as low as $108. However, be on the lookout for offers from Southwest and Delta, as they are both options that can get you from Chicago Midway Airport to San Francisco for a low price.

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

    Looking at all options, your cheapest flight can be booked for $98. While the most popular route (Chicago Midway - San Francisco) can be booked for $179 on average our data indicates $200 when flying from Chicago Midway Airport to San Francisco.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Midway to San Francisco 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 Chicago Midway Airport to San Francisco?

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to San Francisco (average of $276). Flying from Chicago Midway Airport to San Francisco in June is currently the most expensive (average of $358). 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
Roseville
Mountain View
Santa Cruz
South San Francisco
Livermore
Turlock
Manteca
Antioch
Hollister
Watsonville
Newark
Milpitas
Sunnyvale
Campbell
Lathrop
Foster City
Capitola
Santa Clara
San Leandro
Burlingame

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Top 3 airlines flying from Midway to San Francisco

Discover the top 3 airlines that operate flights from Midway to San Francisco. 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 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$118Average$313FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$179Average$322FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$243Average$437FlexibilityNo cancel feeOn-time63%

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