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Cheap flights from Chicago Midway Airport to San Francisco from $100

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to San Francisco departing on 9/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Chicago Midway Airport to San Francisco (MDW-SFO)

Cheap round-trip flights

Southwest Logo
5:25 am - 9:25 amMDW-SFO
6h 00m1 stop
Southwest Logo
9:55 am - 7:05 pmSFO-MDW
7h 10m1 stop
$199Southwest
Find Deal
vie., sep. 5 - sáb., sep. 6
Frontier Logo
1:53 pm - 7:08 pmMDW-SFO
7h 15m1 stop
Frontier Logo
6:29 am - 3:53 pmSFO-MDW
7h 24m1 stop
$200Frontier
Find Deal
jue., oct. 2 - lun., oct. 6
Frontier Logo
6:24 pm - 12:14 amMDW-SFO
7h 50m1 stop
Frontier Logo
10:23 pm - 1:38 pmSFO-MDW
13h 15m1 stop
$201Frontier
Find Deal
jue., oct. 16 - lun., oct. 20
Frontier Logo
1:53 pm - 7:08 pmMDW-SFO
7h 15m1 stop
Frontier Logo
6:29 am - 3:53 pmSFO-MDW
7h 24m1 stop
$202Frontier
Find Deal
jue., oct. 2 - lun., oct. 6
Frontier Logo
1:53 pm - 7:08 pmMDW-SFO
7h 15m1 stop
Frontier Logo
7:07 pm - 3:53 pmSFO-MDW
18h 46m1 stop
$205Frontier
Find Deal
jue., sep. 25 - dom., sep. 28
Frontier Logo
3:48 pm - 12:16 amMDW-SFO
10h 28m1 stop
Frontier Logo
11:57 pm - 10:28 amSFO-MDW
8h 31m1 stop
$206Frontier
Find Deal
vie., sep. 19 - vie., sep. 26
Frontier Logo
3:48 pm - 12:16 amMDW-SFO
10h 28m1 stop
Frontier Logo
6:29 am - 3:53 pmSFO-MDW
7h 24m1 stop
$210Frontier
Find Deal
vie., sep. 19 - vie., sep. 26
Southwest Logo
8:15 am - 11:00 amMDW-SFO
4h 45mnonstop
Southwest Logo
6:10 am - 12:15 pmSFO-MDW
4h 05mnonstop
$231Southwest
Find Deal
sáb., dic. 6 - mar., dic. 9
Delta Logo
9:35 am - 2:13 pmMDW-SFO
6h 38m1 stop
Delta Logo
10:57 pm - 8:40 amSFO-MDW
7h 43m1 stop
$257Delta
Find Deal
mié., oct. 22 - mié., oct. 22
Delta Logo
7:15 pm - 11:59 pmMDW-SFO
6h 44m1 stop
Delta Logo
11:59 am - 9:36 pmSFO-MDW
7h 37m1 stop
$276Delta
Find Deal
lun., sep. 15 - mar., sep. 23

Southwest flights from Chicago Midway Airport to San Francisco

Our best Southwest deals on Chicago Midway Airport to San Francisco flight tickets
Southwest
Sep 5
MDW5:25 amChicago Midway
6h 00m
1 stop
SFO9:25 amSan Francisco
Sep 6
SFO9:55 amSan Francisco
7h 10m
1 stop
MDW7:05 pmChicago Midway
$199
Find similar
Southwest
Dec 6
MDW8:15 amChicago Midway
4h 45m
SFO11:00 amSan Francisco
Dec 9
SFO6:10 amSan Francisco
4h 05m
MDW12:15 pmChicago Midway
$231
Find similar
Southwest
Sep 6
MDW8:15 amChicago Midway
4h 35m
SFO10:50 amSan Francisco
Sep 15
SFO9:05 pmSan Francisco
8h 35m
1 stop
MDW7:40 amChicago Midway
$237
Find similar

Delta flights from Chicago Midway Airport to San Francisco

Our best Delta deals on Chicago Midway Airport to San Francisco flight tickets
Delta
Oct 22
MDW9:35 amChicago Midway
6h 38m
1 stop
SFO2:13 pmSan Francisco
Oct 22
SFO10:57 pmSan Francisco
7h 43m
1 stop
MDW8:40 amChicago Midway
$257
Find similar
Delta
Sep 15
MDW7:15 pmChicago Midway
6h 44m
1 stop
SFO11:59 pmSan Francisco
Sep 23
SFO11:59 amSan Francisco
7h 37m
1 stop
MDW9:36 pmChicago Midway
$276
Find similar
Delta
Aug 31
MDW6:00 amChicago Midway
7h 45m
1 stop
SFO11:45 amSan Francisco
Sep 4
SFO11:35 amSan Francisco
7h 51m
1 stop
MDW9:26 pmChicago Midway
$297
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport 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, momondo users made 832,500 searches. Data last updated agosto 25, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to San Francisco that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

vie. 9/5

5:25 am-9:25 am

1 stop6h 00m

San Francisco

sáb. 9/6

9:55 am-7:05 pm

1 stop7h 10m

$199

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

jue. 10/2

1:53 pm-7:08 pm

1 stop7h 15m

San Francisco

lun. 10/6

6:29 am-3:53 pm

1 stop7h 24m

$200

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

jue. 10/16

6:24 pm-12:14 am

1 stop7h 50m

San Francisco

lun. 10/20

10:23 pm-1:38 pm

1 stop13h 15m

$201

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

jue. 10/2

1:53 pm-7:08 pm

1 stop7h 15m

San Francisco

lun. 10/6

6:29 am-3:53 pm

1 stop7h 24m

$202

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

jue. 9/25

1:53 pm-7:08 pm

1 stop7h 15m

San Francisco

dom. 9/28

7:07 pm-3:53 pm

1 stop18h 46m

$205

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

vie. 9/19

3:48 pm-12:16 am

1 stop10h 28m

San Francisco

vie. 9/26

11:57 pm-10:28 am

1 stop8h 31m

$206

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

vie. 9/19

3:48 pm-12:16 am

1 stop10h 28m

San Francisco

vie. 9/26

6:29 am-3:53 pm

1 stop7h 24m

$210

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

sáb. 12/6

8:15 am-11:00 am

Nonstop4h 45m

San Francisco

mar. 12/9

6:10 am-12:15 pm

Nonstop4h 05m

$231

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

mié. 10/22

9:35 am-2:13 pm

1 stop6h 38m

San Francisco

mié. 10/22

10:57 pm-8:40 am

1 stop7h 43m

$257

ChicagoSan Francisco

MDW - SFO

MDWSFO

Chicago Midway

lun. 9/15

7:15 pm-11:59 pm

1 stop6h 44m

San Francisco

mar. 9/23

11:59 am-9:36 pm

1 stop7h 37m

$276

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to San Francisco from

How to get the cheapest flight ticket from Chicago Midway Airport to San Francisco

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to San Francisco?

If you aren’t able to travel to San Francisco during the month of November, then flying in September is also cheap. Prices for this month can be found on momondo for an average of $309.

What is the cheapest day to depart on your flight to San Francisco?

The cheapest day to depart from Chicago Midway Airport to San Francisco is on a Thursday when prices can be found for as low as $351. The most expensive day to fly to San Francisco is Sunday, with ticket prices averaging around $520.

What is the cheapest time of day to depart on your flight to San Francisco?

Our data shows that the cheapest Chicago Midway Airport to San Francisco flights are usually those with departure times in the evening. Our users have found flights to San Francisco in the evening for as low as $373. Flights in the afternoon are often more expensive with an average ticket price of $452.

What is the cheapest Chicago Midway to San Francisco flight route?

Fly from Chicago Midway to San Francisco for the best Chicago Midway - San Francisco flight prices

What cabin class options are available on Chicago Midway to San Francisco flights?

There are 1 cabin classes available to choose from on Chicago Midway to San Francisco flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago Midway Airport to San Francisco flights?

You could potentially save up to 9% on your flight if you consider stops on a Chicago Midway Airport to San Francisco flight.

How have Chicago Midway Airport to San Francisco flight prices changed over time?

As of August 2025, prices for Chicago Midway Airport to San Francisco flights are approximately 28% more expensive when compared to flights at the same time last year.

When to book flights from Chicago Midway Airport to San Francisco

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to San Francisco according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to San Francisco (MDW to SFO) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to San Francisco

Best Price Found

$108

Fastest flight time

4h 30m

Direct flights

Every day

Airports in San Francisco

1 airport
The best one-way flight to San Francisco from Chicago Midway Airport in the past 72 hours is $108. The best round-trip flight deal from Chicago Midway Airport to San Francisco found on momondo in the last 72 hours is $207.
The fastest flight from Chicago Midway Airport to San Francisco takes 4h 30m
Direct flights go from Chicago Midway Airport to San Francisco every day.
There is 1 airport near San Francisco: San Francisco (SFO)
Search flight deals

  • How far is Chicago Midway to San Francisco by plane?

    Chicago Midway and San Francisco are 1847.1 mi apart from one another. Typically, this will take 4h 30m by plane in normal conditions.

  • When did momondo last update prices for flights from Chicago Midway Airport to San Francisco Airport?

    Prices for flights from Chicago Midway Airport to San Francisco Airport are updated daily.

  • How many operators does momondo search for flights from Chicago Midway Airport to San Francisco Airport?

  • How old do you have to be to fly from Chicago Midway Airport to San Francisco Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago Midway Airport to San Francisco Airport.

  • What documentation or ID do you need to fly to San Francisco Airport?

    The travel and health documents you'll need for your trip to San Francisco Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at San Francisco Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Chicago Midway Airport to San Francisco?

  • What is the most popular airline from Chicago Midway Airport to San Francisco?

Best airlines flying from Chicago Midway Airport to San Francisco

Compare and see reviews for airlines that fly from Chicago Midway Airport to San Francisco with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $132Free CancellationRating
5.8
3,201 reviews
Search Frontier flights
United AirlinesPriceFrom $217Free CancellationRating
7.4
8,940 reviews
Search United Airlines flights
SouthwestPriceFrom $233Free CancellationRating
8.0
4,243 reviews
Search Southwest flights

  • Southwest Flights From Chicago Midway Airport to San Francisco

    Southwest operates around 12 flights from Chicago Midway Airport to San Francisco every week. The average price of these flights found in the last 72 hours has been $441, but momondo users have found Southwest deals from Chicago Midway Airport to San Francisco from as low as $233 round-trip. Southwest has been scored 8.0/10 in 4,243 reviews.

Traveling to a place near San Francisco?

Book flights to San Francisco if you plan to visit one of these locations
Santa Cruz
Carmel-by-the-Sea
Modesto
Sonoma
Calistoga
Hayward
Bodega Bay
Roseville
Santa Clara
Big Sur
Daly City
Fremont
Berkeley
Walnut Creek
Half Moon Bay
South San Francisco
Vallejo
Redwood City
Pacific Grove
Salinas

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to San Francisco?

It is quick and easy to find Chicago to San Francisco flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to San Francisco that suits you.

Can I find flights from Chicago to San Francisco with flexible booking policies on momondo?

Yes. All flights to San Francisco from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Chicago to San Francisco?

momondo provides multiple filters to help you find the best flight to San Francisco from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to San Francisco right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Chicago to San Francisco now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to San Francisco and let you know when they change.

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