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Midway

$99+ 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 10/26. Fares are subject to change and may not be available on all flights or dates of travel.
SFO — MDW
Oct 26 — Nov 21
Sun 10/26
Sun 11/2
1 adult, Economy
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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 September 26, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$213
(Kiwi.com)

One-way from

$99
(Trip.com)

Popular in

December

Cheapest in

February

Average price

$317
Provider with most accurate pricing for San Francisco-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for San Francisco-Chicago (CHI) flights.
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From San Francisco Bay Area to Chicago Midway
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One-way flight from San Francisco Bay Area to Chicago Midway
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Highest demand for flights based on searches. 9% potential increase in price ($36 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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 September 26, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/116:21 amSFO - MDW
1 stop12h 15mFrontier
Mon 12/152:45 pmMDW - SFO
1 stop11h 40mFrontier
Deal found 9/25$213
This Booking.com deal was found by Cheapflights users on 9/26. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/304:06 pmSFO - MDW
1 stop23h 09mFrontier
Sun 11/29:00 amMDW - SFO
1 stop9h 43mFrontier
Deal found 9/26$216
This Frontier deal was found by Cheapflights users on 9/26. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/235:45 amSFO - MDW
2 stops15h 35mFrontier
Mon 10/275:10 amMDW - SFO
1 stop12h 50mFrontier
Deal found 9/26$217
This Frontier deal was found by Cheapflights users on 9/23. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/146:34 amSFO - MDW
2 stops13h 34mFrontier
Mon 11/171:37 pmMDW - SFO
2 stops12h 37mFrontier
Deal found 9/23$218
This Frontier deal was found by Cheapflights users on 9/24. 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.
Mon 10/1310:23 pmSFO - MDW
1 stop13h 15mFrontier
Fri 10/175:10 amMDW - SFO
1 stop12h 50mFrontier
Deal found 9/24$219
This Kiwi.com deal was found by Cheapflights users on 9/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/57:30 amSFO - MDW
2 stops23h 42mFrontier
Sat 11/81:37 pmMDW - SFO
1 stop9h 34mFrontier
Deal found 9/26$220
This Frontier deal was found by Cheapflights users on 9/23. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/256:44 amSFO - MDW
2 stops14h 03mFrontier
Sat 11/86:15 amMDW - SFO
2 stops12h 28mFrontier
Deal found 9/23$222
This Kiwi.com deal was found by Cheapflights users on 9/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/59:17 amSFO - MDW
1 stop10h 11mFrontier
Mon 12/152:45 pmMDW - SFO
1 stop11h 40mFrontier
Deal found 9/25$223
This Booking.com deal was found by Cheapflights users on 9/24. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/78:55 pmSFO - MDW
1 stop15h 02mFrontier
Mon 11/1012:30 pmMDW - SFO
1 stop13h 44mFrontier
Deal found 9/24$224
This Kiwi.com deal was found by Cheapflights users on 9/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/65:45 amSFO - MDW
2 stops14h 18mFrontier
Mon 11/1012:30 pmMDW - SFO
1 stop13h 44mFrontier
Deal found 9/24$226
This Booking.com deal was found by Cheapflights users on 9/24. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1012:35 pmSJC - MDW
1 stop9h 49mFrontier
Sun 10/126:24 pmMDW - SJC
1 stop19h 08mFrontier
Deal found 9/24$228
This Frontier deal was found by Cheapflights users on 9/26. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/2612:27 pmSJC - MDW
1 stop10h 09mFrontier
Thu 10/309:43 pmMDW - SJC
2 stops15h 49mFrontier
Deal found 9/26$231

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 September 26, 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

Mon 11/10

12:30 am-9:01 am

1 stop6h 31m

Chicago Midway

Tue 11/18

6:00 am-12:30 pm

1 stop8h 30m

$263

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Wed 10/29

6:30 am-12:35 pm

Nonstop4h 05m

Chicago Midway

Mon 11/3

6:20 am-1:55 pm

1 stop9h 35m

$271

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Wed 10/22

6:30 am-12:35 pm

Nonstop4h 05m

Chicago Midway

Sat 10/25

5:15 pm-9:25 pm

1 stop6h 10m

$281

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Sat 11/1

6:10 am-3:26 pm

1 stop7h 16m

Chicago Midway

Tue 11/4

1:08 pm-5:51 pm

1 stop6h 43m

$291

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Tue 10/21

12:35 am-8:55 am

1 stop6h 20m

Chicago Midway

Mon 10/27

7:10 pm-12:05 am

1 stop6h 55m

$293

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Mon 10/20

6:00 am-12:05 pm

Nonstop4h 05m

Chicago Midway

Tue 10/28

2:45 pm-5:15 pm

Nonstop4h 30m

$299

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Thu 10/23

8:55 am-5:55 pm

1 stop7h 00m

Chicago Midway

Thu 10/30

8:00 am-12:25 pm

1 stop6h 25m

$299

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Sat 10/25

5:55 am-6:25 pm

2 stops10h 30m

Chicago Midway

Wed 10/29

9:20 am-4:11 pm

2 stops8h 51m

$301

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Thu 11/13

8:55 pm-5:15 am

1 stop6h 20m

Chicago Midway

Mon 11/17

12:05 pm-6:20 pm

2 stops8h 15m

$304

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Tue 11/4

7:35 pm-8:55 am

2 stops11h 20m

Chicago Midway

Wed 11/5

5:09 pm-10:58 pm

1 stop7h 49m

$308

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/25

Showing 1-10 of 56 results
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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 September 26, 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 September 26, 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

Overall

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

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

Overall

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

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
7,973 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

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
8,926 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

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

Overall

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

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
3,162 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

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.

  • How long is the flight from San Francisco Bay Area to Chicago Midway Airport?

    Departing from San Francisco Bay Area to Chicago Midway Airport will take you 4h 05m. San Francisco Bay Area and Chicago Midway Airport are separated by a distance of 1849 mi. This flight may include one or multiple stops.

  • 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 $340, our data indicates the cheapest price to be $148. The most popular route (San Francisco - Chicago Midway), is priced around $260.

  • 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

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Alternative routes for San Francisco Bay Area to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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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 September 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$128Average$247FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$133Average$347FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$197Average$332FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$197Average$280FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$217Average$443FlexibilityNo cancel feeOn-time63%
DeltaCheapest$256Average$357FlexibilityNo cancel feeOn-timeN/A

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