HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$109+ 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 9/4. Fares are subject to change and may not be available on all flights or dates of travel.
SFO — MDW
Jul 23 — Jul 301
Wed 7/23
Wed 7/30
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

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 Friday or Saturday 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 18, 2025.

Round-trip from

$207
(Southwest)

One-way from

$109
(Southwest)

Popular in

December

Cheapest in

January

Average price

$346

Good round-trip deal

$278 or less

Good one-way deal

$183 or less
From San Francisco to Chicago Midway
Search Deals
One-way flight from San Francisco to Chicago Midway
Search Deals
High demand for flights, 6% potential price rise
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2025
Search Deals
Price to beat on a round-trip flight from San Francisco to Chicago Midway.
Search Deals
Price to beat on a one-way flight from San Francisco to Chicago Midway.
Search Deals

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 18, 2025.

This Southwest deal was found by Cheapflights users on 7/15. 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 9/47:15 amSFO - MDW
Nonstop4h 05mSouthwest
Wed 9/103:50 pmMDW - SFO
Nonstop4h 35mSouthwest
Deal found 7/15$207
This Priceline deal was found by Cheapflights users on 7/15. 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.
Mon 8/1110:29 pmSFO - MDW
1 stop10h 11mFrontier
Wed 8/1311:39 amMDW - SFO
1 stop11h 44mFrontier
Deal found 7/15$213
This Delta deal was found by Cheapflights users on 7/15. 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 8/1512:40 amSFO - MDW
1 stop6h 10mDelta
Tue 8/191:08 pmMDW - SFO
1 stop6h 39mDelta
Deal found 7/15$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 18, 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

Thu 9/4

7:15 am-1:20 pm

Nonstop4h 05m

Chicago Midway

Wed 9/10

3:50 pm-6:25 pm

Nonstop4h 35m

$207

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Mon 8/11

10:29 pm-10:40 am

1 stop10h 11m

Chicago Midway

Wed 8/13

11:39 am-9:23 pm

1 stop11h 44m

$213

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Fri 8/15

12:40 am-8:50 am

1 stop6h 10m

Chicago Midway

Tue 8/19

1:08 pm-5:47 pm

1 stop6h 39m

$257

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Thu 9/4

7:15 am-1:20 pm

Nonstop4h 05m

$109

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Mon 9/29

6:29 am-3:53 pm

1 stop7h 24m

$118

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Mon 8/11

12:40 am-8:50 am

1 stop6h 10m

$129

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/15

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 July 11, 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 July 18, 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 July 13, 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 18, 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
4,239 reviews

Overall

8.0

Entertainment

7.6

Food

7.0

Comfort

8.0

Boarding

8.1

Crew

8.6

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
4,239 reviews
Southwest
8.0
Very good
4,239 reviews

Overall

8.0

Entertainment

7.6

Food

7.0

Comfort

8.0

Boarding

8.1

Crew

8.6

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
7,959 reviews
Southwest
8.0
Very good
4,239 reviews

Overall

8.0

Entertainment

7.6

Food

7.0

Comfort

8.0

Boarding

8.1

Crew

8.6

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
3,250 reviews
Southwest
8.0
Very good
4,239 reviews

Overall

8.0

Entertainment

7.6

Food

7.0

Comfort

8.0

Boarding

8.1

Crew

8.6

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 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 $207. Other airlines that can offer you cheap pricing are Frontier, from $213, and Delta, from $257. These flights start at 36% 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 $109. Frontier flights start at $118 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 $329 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for San Francisco to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Los Angeles to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Ontario to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Burbank to O'Hare Intl flights
San Diego to O'Hare Intl flights
San Jose to O'Hare Intl flights
Los Angeles to Midway flights
Oakland to O'Hare Intl flights
Sacramento to O'Hare Intl flights
Las Vegas to O'Hare Intl flights
San Diego to Midway flights
San Jose to Midway flights
Sacramento to Midway flights
Ontario to Midway flights
Las Vegas to Midway flights
Oakland to Midway flights
Santa Ana to Midway flights
Fresno to O'Hare Intl flights
Long Beach to O'Hare Intl flights
Palm Springs to O'Hare Intl flights
Burbank to Midway flights
Reno to O'Hare Intl flights
Monterey to O'Hare Intl flights
Fresno to Midway flights
Palm Springs to Midway flights
Santa Barbara to O'Hare Intl flights
Santa Rosa to O'Hare Intl flights
Long Beach to Midway flights
Reno to Midway flights
Los Angeles to Rockford flights
Bakersfield to O'Hare Intl flights
San Luis Obispo to O'Hare Intl flights
Medford to O'Hare Intl flights
Las Vegas to Rockford flights
Redding to O'Hare Intl flights
San Diego to Rockford flights
Oakland to Rockford flights
Medford to Midway flights
Tijuana to O'Hare Intl flights
Yuma to O'Hare Intl flights
Arcata to O'Hare Intl flights
Tijuana to Midway flights
San Francisco to Rockford flights
Burbank to Rockford flights
Bakersfield to Midway flights
San Jose to Rockford flights
Sacramento to Rockford flights

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 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$118Average$231FlexibilityNo 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$211Average$400FlexibilityNo cancel feeOn-time63%
DeltaCheapest$236Average$337FlexibilityNo cancel feeOn-timeN/A

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.