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Midway

$103+ 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 2/5. Fares are subject to change and may not be available on all flights or dates of travel.
SFO — MDW
Jan 29 — Feb 51
Thu 1/29
Thu 2/5
1 adult, Economy
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Cheap 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 December 30, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/28. 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.
Tue 12/308:16 pmSFO - MDW
1 stop11h 05mFrontier
Mon 1/58:15 amMDW - SFO
2 stops29h 39mFrontier
Deal found 12/28$576
This Kiwi.com deal was found by Cheapflights users on 12/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/308:16 pmSFO - MDW
1 stop11h 05mFrontier
Thu 1/17:44 amMDW - SFO
2 stops31h 29mFrontier
Deal found 12/27$698
This Delta deal was found by Cheapflights users on 12/28. 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.
Tue 12/304:50 pmOAK - MDW
2 stops14h 15mDelta
Fri 1/29:29 amMDW - OAK
2 stops8h 35mDelta
Deal found 12/28$699
This Delta deal was found by Cheapflights users on 12/28. 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.
Wed 12/3112:11 pmSFO - MDW
1 stop8h 11mDelta
Mon 1/56:14 pmMDW - SFO
1 stop7h 11mDelta
Deal found 12/28$702
This Kiwi.com deal was found by Cheapflights users on 12/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/308:16 pmSFO - MDW
1 stop11h 05mFrontier
Sun 1/46:00 amMDW - SFO
2 stops20h 24mFrontier
Deal found 12/27$709
This Delta deal was found by Cheapflights users on 12/29. 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.
Tue 12/3011:45 pmSFO - MDW
1 stop7h 20mDelta
Mon 1/56:14 pmMDW - SFO
1 stop7h 11mDelta
Deal found 12/29$722
This Delta deal was found by Cheapflights users on 12/27. 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 12/2710:45 pmSFO - MDW
1 stop8h 04mDelta
Sat 1/36:00 amMDW - SFO
1 stop8h 51mDelta
Deal found 12/27$788
This Southwest deal was found by Cheapflights users on 12/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/306:45 amSFO - MDW
Nonstop4h 00mSouthwest
Sat 1/34:20 pmMDW - SFO
1 stop8h 30mSouthwest
Deal found 12/27$814
This Delta deal was found by Cheapflights users on 12/27. 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.
Sun 12/284:50 pmOAK - MDW
2 stops14h 15mDelta
Fri 1/29:29 amMDW - OAK
2 stops8h 35mDelta
Deal found 12/27$819
This Kiwi.com deal was found by Cheapflights users on 12/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/308:16 pmSFO - MDW
1 stop11h 05mFrontier
Sat 1/36:12 amMDW - SFO
2 stops16h 18mFrontier
Deal found 12/27$827
This Delta deal was found by Cheapflights users on 12/27. 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 12/2710:45 pmSFO - MDW
1 stop8h 04mDelta
Tue 12/3012:45 pmMDW - SFO
1 stop10h 05mDelta
Deal found 12/27$857
This Kiwi.com deal was found by Cheapflights users on 12/28. 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 12/3111:20 pmSFO - MDW
1 stop20h 52mFrontier
Mon 1/56:12 amMDW - SFO
2 stops31h 42mFrontier
Deal found 12/28$865

Find 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 December 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$242
(Southwest)

One-way from

$103
(Kiwi.com)

Popular in

December

Cheapest in

February

Average price

$459
Provider with most accurate pricing for San Francisco-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for San Francisco-Chicago (CHI) flights.
Search Deals
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. 14% potential increase in price ($56 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 30, 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

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Wed 2/11

11:10 am-5:15 pm

Nonstop4h 05m

Chicago Midway

Wed 2/18

5:05 am-12:35 pm

1 stop9h 30m

$242

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Wed 1/28

9:30 pm-9:05 am

1 stop9h 35m

Chicago Midway

Sat 1/31

8:15 am-11:15 am

Nonstop5h 00m

$261

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Tue 2/17

6:25 am-12:25 pm

Nonstop4h 00m

Chicago Midway

Tue 2/17

1:35 pm-9:55 pm

2 stops10h 20m

$262

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Thu 1/29

10:54 pm-8:52 am

1 stop7h 58m

Chicago Midway

Fri 1/30

7:16 pm-11:47 pm

1 stop6h 31m

$263

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Wed 2/11

12:40 am-9:06 am

1 stop6h 26m

Chicago Midway

Sat 2/21

1:28 pm-6:36 pm

1 stop7h 08m

$266

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Thu 2/12

6:40 am-12:45 pm

Nonstop4h 05m

Chicago Midway

Sat 2/21

8:55 pm-11:50 pm

Nonstop4h 55m

$269

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Wed 3/18

5:40 am-11:40 am

Nonstop4h 00m

Chicago Midway

Wed 3/25

9:05 pm-11:45 pm

Nonstop4h 40m

$270

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Sat 2/21

6:05 am-4:14 pm

1 stop8h 09m

Chicago Midway

Tue 2/24

1:26 pm-10:41 pm

2 stops11h 15m

$275

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Mon 1/19

10:54 pm-8:52 am

1 stop7h 58m

Chicago Midway

Thu 1/29

7:16 pm-11:47 pm

1 stop6h 31m

$283

San FranciscoChicago

SFO - MDW

SFOMDW

San Francisco

Thu 2/12

5:55 am-11:55 am

Nonstop4h 00m

Chicago Midway

Sun 2/15

8:15 am-11:15 am

Nonstop5h 00m

$283

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/28

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, January is the cheapest month in which you can book a flight from San Francisco Bay Area to Chicago Midway Airport (average of $139). Flying from San Francisco Bay Area to Chicago Midway Airport in June is currently the most expensive (average of $242). 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 December 30, 2025.

It’s optimal to fly from San Francisco Bay Area to Chicago Midway Airport in the afternoon. By choosing this option you can save up to 38% on the cost of your flight, compared to a flight at noon.

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 December 30, 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
4,251 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Southwest
8.0
Very good
4,251 reviews
Southwest
8.0
Very good
4,251 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Delta
7.9
Good
8,014 reviews
Southwest
8.0
Very good
4,251 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
United Airlines
7.4
Good
9,121 reviews
Southwest
8.0
Very good
4,251 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
American Airlines
7.2
Good
11,072 reviews
Southwest
8.0
Very good
4,251 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Frontier
5.7
Fair
3,065 reviews
Southwest
8.0
Very good
4,251 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.

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 1839 mi. This flight may include one or multiple stops.

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

    $81 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on United Airlines and Southwest, with prices starting from $98 and $108, respectively.

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

    While some choose either Oakland - Chicago Midway or San Jose - 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 $399, our data indicates the cheapest price to be $154. The most popular route (San Francisco - Chicago Midway), is priced around $205.

  • 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, January is the cheapest month in which you can book a flight from San Francisco Bay Area to Chicago Midway Airport (average of $139). Flying from San Francisco Bay Area to Chicago Midway Airport in June is currently the most expensive (average of $242). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

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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 5 airlines flying from San Francisco Bay Area to Midway

Discover the top 5 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 December 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$133Average$439FlexibilityNo cancel feeOn-time69%
FrontierCheapest$147Average$237FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$197Average$332FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$217Average$451FlexibilityNo cancel feeOn-time63%
DeltaCheapest$256Average$338FlexibilityNo cancel feeOn-timeN/A

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