HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$78+ Cheap flights from San Francisco Bay Area 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 9/25. Fares are subject to change and may not be available on all flights or dates of travel.
SFO — MDW
Aug 18 — Aug 251
Mon 8/18
Mon 8/25
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from San Francisco Bay Area 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.

Cheap flight deals from San Francisco Bay Area to Midway

Keep the following information in mind while searching for San Francisco Bay Area to Midway flight deals. Data was last updated August 13, 2025.

Round-trip from

$207
(Southwest)

One-way from

$78
(Kiwi.com)

Popular in

December

Cheapest in

February

Average price

$366
From San Francisco Bay Area to Chicago Midway
Search Deals
One-way flight from San Francisco Bay Area to Chicago Midway
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($25 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2025
Search Deals

Find flight deals from San Francisco Bay Area to Midway

Cheapest flights from San Francisco Bay Area to Midway
Explore the most affordable flight options available from San Francisco Bay Area to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 13, 2025.

This Southwest deal was found by Cheapflights users on 8/12. 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.
Mon 10/276:00 amSFO - MDW
Nonstop4h 05mSouthwest
Wed 11/198:15 amMDW - SFO
Nonstop4h 45mSouthwest
Deal found 8/12$207
This Southwest deal was found by Cheapflights users on 8/12. 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.
Fri 11/143:55 pmSFO - MDW
1 stop6h 10mSouthwest
Tue 11/188:15 amMDW - SFO
Nonstop4h 45mSouthwest
Deal found 8/12$217
This Southwest deal was found by Cheapflights users on 8/13. 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.
Fri 11/75:25 amOAK - MDW
Nonstop4h 05mSouthwest
Tue 11/115:30 amMDW - OAK
1 stop6h 20mSouthwest
Deal found 8/13$217
This Southwest deal was found by Cheapflights users on 8/12. 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 10/184:10 pmSFO - MDW
1 stop10h 50mSouthwest
Tue 10/214:10 pmMDW - SFO
1 stop7h 00mSouthwest
Deal found 8/12$222
This Southwest deal was found by Cheapflights users on 8/12. 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.
Fri 11/77:45 amSFO - MDW
2 stops8h 45mSouthwest
Mon 11/108:20 amMDW - SFO
Nonstop4h 45mSouthwest
Deal found 8/12$232
This Priceline deal was found by Cheapflights users on 8/11. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/233:25 pmSFO - MDW
1 stop7h 11mFrontier
Mon 10/276:24 pmMDW - SFO
1 stop7h 50mFrontier
Deal found 8/11$235
This Southwest deal was found by Cheapflights users on 8/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1610:45 amSFO - MDW
Nonstop4h 10mSouthwest
Tue 9/233:50 pmMDW - SFO
Nonstop4h 35mSouthwest
Deal found 8/11$236
This Southwest deal was found by Cheapflights users on 8/12. 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.
Wed 9/178:05 amSJC - MDW
1 stop7h 40mSouthwest
Sat 9/203:35 pmMDW - SJC
Nonstop4h 30mSouthwest
Deal found 8/12$236
This Southwest deal was found by Cheapflights users on 8/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/215:50 amOAK - MDW
Nonstop4h 05mSouthwest
Sat 10/253:55 pmMDW - OAK
Nonstop4h 35mSouthwest
Deal found 8/11$236
This Southwest deal was found by Cheapflights users on 8/12. 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.
Fri 10/315:30 amSFO - MDW
Nonstop4h 00mSouthwest
Mon 11/38:15 amMDW - SFO
Nonstop4h 45mSouthwest
Deal found 8/12$237
This Priceline deal was found by Cheapflights users on 8/11. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/410:19 amSFO - MDW
1 stop9h 39mFrontier
Mon 9/84:48 pmMDW - SFO
1 stop9h 28mFrontier
Deal found 8/11$238
This Southwest deal was found by Cheapflights users on 8/12. 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.
Wed 9/39:05 pmSFO - MDW
1 stop9h 55mSouthwest
Sat 9/68:15 amMDW - SFO
Nonstop4h 35mSouthwest
Deal found 8/12$241

Cheapflights Fare Finder

 
Customize your flight search to find flights from San Francisco Bay Area 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 August 13, 2025.
Use the filters below to find and compare flights from San Francisco Bay Area to Chicago Midway Airport that are best for you.

Fly from

San Francisco Bay Area

Fly to

Midway

Route

Depart

Return

Price

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Sat 11/8

12:35 pm-8:25 pm

1 stop5h 50m

Chicago Midway

Tue 11/11

8:15 am-11:00 am

Nonstop4h 45m

$207

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Tue 9/16

11:00 am-10:00 pm

1 stop9h 00m

Chicago Midway

Tue 9/23

3:50 pm-6:25 pm

Nonstop4h 35m

$207

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Tue 10/21

6:30 am-12:35 pm

Nonstop4h 05m

Chicago Midway

Wed 11/5

12:20 pm-6:35 pm

1 stop8h 15m

$207

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Wed 10/22

6:30 am-12:35 pm

Nonstop4h 05m

Chicago Midway

Sun 11/9

8:20 am-11:05 am

Nonstop4h 45m

$207

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Mon 10/27

6:00 am-12:05 pm

Nonstop4h 05m

Chicago Midway

Sat 11/15

8:15 am-11:00 am

Nonstop4h 45m

$207

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Thu 9/4

7:15 am-1:20 pm

Nonstop4h 05m

Chicago Midway

Tue 9/9

3:50 pm-6:25 pm

Nonstop4h 35m

$207

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Wed 10/15

1:05 pm-11:35 pm

1 stop8h 30m

Chicago Midway

Sat 10/25

8:15 am-10:50 am

Nonstop4h 35m

$207

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Sat 9/20

6:20 pm-5:10 am

1 stop8h 50m

Chicago Midway

Tue 9/23

3:50 pm-6:25 pm

Nonstop4h 35m

$207

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Mon 10/27

6:00 am-12:05 pm

Nonstop4h 05m

Chicago Midway

Wed 11/19

8:15 am-11:00 am

Nonstop4h 45m

$207

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Wed 10/29

6:30 am-12:35 pm

Nonstop4h 05m

Chicago Midway

Mon 11/3

8:15 am-11:00 am

Nonstop4h 45m

$207

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/11

Showing 1-10 of 53 results
1
2
3
...
6

Best time to book a flight from San Francisco Bay Area to Midway

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

What is the cheapest month to book a flight from San Francisco Bay Area to Chicago Midway Airport?

Currently, April is the cheapest month in which you can book a flight from San Francisco Bay Area to Chicago Midway Airport (average of $160). Flying from San Francisco Bay Area 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 XIH to MDW?

Find hourly flight availability from San Francisco Bay Area 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 August 13, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from San Francisco Bay Area to Chicago Midway Airport as you normally would.

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 August 13, 2025.
See what other customers who have flown with Southwest, Delta, and United Airlines from San Francisco Bay Area to Chicago Midway Airport have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Delta
8.0
Very good
7,979 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
United Airlines
7.4
Good
8,920 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Frontier
5.8
Fair
3,221 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

Related info for your journey

Find useful and relevant information for your journey from San Francisco Bay Area to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the most popular routes from San Francisco Bay Area to Chicago Midway Airport?

    While some choose either San Jose - Chicago Midway or Oakland - Chicago Midway, San Francisco - Chicago Midway is the most popular route from San Francisco Bay Area to Chicago Midway Airport.

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

    Looking for the cheapest flight from San Francisco Bay Area to Chicago Midway Airport? While on average our users pay $313, our data indicates the cheapest price to be $108. The most popular route (San Francisco - Chicago Midway), is priced around $197.

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

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

  • How can I find direct flights from San Francisco Bay Area 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 Bay Area to Midway.

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

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

    Currently, April is the cheapest month in which you can book a flight from San Francisco Bay Area to Chicago Midway Airport (average of $160). Flying from San Francisco Bay Area 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
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 Bay Area 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
San Francisco to Midway flights
Los Angeles to Midway flights
San Diego to O'Hare Intl flights
San Jose to O'Hare Intl flights
Burbank to O'Hare Intl flights
Oakland to O'Hare Intl flights
Sacramento to O'Hare Intl flights
Las Vegas to O'Hare Intl flights
San Jose to Midway flights
Ontario to Midway flights
San Diego to Midway flights
Fresno to O'Hare Intl flights
Long Beach to O'Hare Intl flights
Oakland to Midway flights
Santa Ana to Midway flights
Las Vegas to Midway flights
Palm Springs to O'Hare Intl flights
Burbank to Midway flights
Reno to O'Hare Intl flights
Sacramento to Midway flights
Long Beach to Midway flights
Monterey to O'Hare Intl flights
Fresno to Midway flights
Santa Barbara to O'Hare Intl flights
Reno to Midway flights
Los Angeles to Rockford flights
Palm Springs to Midway flights
Santa Rosa to O'Hare Intl flights
San Luis Obispo to O'Hare Intl flights
Bakersfield to O'Hare Intl flights
San Jose to Rockford flights
Medford to O'Hare Intl flights
Arcata to O'Hare Intl flights
San Francisco to Rockford flights
Las Vegas to Rockford flights
Medford to Midway flights
Redding to O'Hare Intl flights
Oakland to Rockford flights
Sacramento to Rockford flights
San Diego to Rockford flights
Ontario to Rockford flights
Tijuana to O'Hare Intl flights
Tijuana to Midway flights
Yuma to O'Hare Intl flights
Bakersfield to Midway flights

Top 6 airlines flying from San Francisco Bay Area to Midway

Discover the top 6 airlines that operate flights from San Francisco Bay Area 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 August 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$118Average$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$209Average$436FlexibilityNo cancel feeOn-time63%
DeltaCheapest$256Average$346FlexibilityNo 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.