MDW - SFO

$133 Find Cheap Flights from Chicago Midway Airport to San Francisco

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to San Francisco departing on 6/4. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to San Francisco

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to San Francisco, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to San Francisco, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$270
Typical prices: $567-$400
Frontier
lör 7/18sön 7/19
MDW - SFO • 1 stop
Cheapest non-stop
$272
Typical prices: $590-$409
Southwest
tis 8/11mån 8/17
MDW - SFO • Non-stop
Top airlines
Cheapest • from $270 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with Southwest. Average duration is 4h 36m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Avoid delays
Most punctual • 72% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $324 (round-trip)
Shortest trip • 6h 15m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 30% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to San Francisco!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Midway to San Francisco (MDW-SFO)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to San Francisco that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to San Francisco

lör, jul 18 - sön, jul 19
Frontier Logo
6:00 am - 7:13 pm
MDW
-
SFO
15h 13m
1 stop
Frontier Logo
12:24 am - 2:27 pm
SFO
-
MDW
12h 03m
1 stop
$270Frontier
tis, aug 11 - ons, aug 19
Southwest Logo
8:30 pm - 11:05 pm
MDW
-
SFO
4h 35mnonstop
Southwest Logo
6:00 am - 5:10 pm
SFO
-
MDW
9h 10m
2 stops
$272Southwest
ons, maj 27 - mån, jun 1
Frontier Logo
6:00 am - 7:34 pm
MDW
-
SFO
15h 34m
1 stop
Frontier Logo
10:05 pm - 11:12 am
SFO
-
MDW
11h 07m
1 stop
$274Frontier
ons, sep 2 - tis, sep 8
Delta Logo
1:05 pm - 7:24 pm
MDW
-
SFO
8h 19m
1 stop
Delta Logo
6:00 am - 3:27 pm
SFO
-
MDW
7h 27m
1 stop
$277Delta
ons, jul 15 - sön, jul 19
Frontier Logo
12:11 pm - 7:13 pm
MDW
-
SFO
9h 02m
1 stop
Frontier Logo
10:10 pm - 11:07 am
SFO
-
MDW
10h 57m
1 stop
$278Frontier
fre, maj 29 - sön, aug 9
Frontier Logo
12:04 pm - 7:34 pm
MDW
-
SFO
9h 30m
1 stop
Frontier Logo
12:24 am - 2:27 pm
SFO
-
MDW
12h 03m
1 stop
$280Frontier
tors, jun 4 - ons, jun 10
Southwest Logo
9:30 pm - 12:10 am
MDW
-
SFO
4h 40mnonstop
Southwest Logo
3:10 pm - 12:05 am
SFO
-
MDW
6h 55m
1 stop
$282Southwest
tors, jul 23 - lör, jul 25
Frontier Logo
6:00 am - 7:13 pm
MDW
-
SFO
15h 13m
1 stop
Frontier Logo
12:24 am - 2:27 pm
SFO
-
MDW
12h 03m
1 stop
$284Frontier
ons, aug 12 - tis, aug 25
Southwest Logo
8:50 am - 4:25 pm
MDW
-
SFO
9h 35m
2 stops
Southwest Logo
6:00 am - 5:10 pm
SFO
-
MDW
9h 10m
2 stops
$287Southwest
ons, jul 22 - sön, jul 26
Frontier Logo
6:00 am - 7:13 pm
MDW
-
SFO
15h 13m
1 stop
Frontier Logo
12:24 am - 2:27 pm
SFO
-
MDW
12h 03m
1 stop
$289Frontier
Booking Insights

KAYAK's insights & trends for Midway to San Francisco flights

Get data-powered insights and trends into flights from Midway to San Francisco to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Chicago Midway Airport to San Francisco?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago Midway Airport to San Francisco departing in July.

What’s the cheapest day of the week to fly from Chicago Midway Airport to San Francisco?

The average price of all round-trip flights from Chicago Midway Airport to San Francisco clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to San Francisco on a Wednesday, as we generally find the cheapest rates on that day for this route. On the other hand, Monday is the most expensive day to fly from Chicago Midway Airport to San Francisco. For your return ticket, we recommend flying on a Wednesday and avoiding Sundays for the best deals.

What is the cheapest month to fly from Chicago Midway Airport to San Francisco?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to San Francisco, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago Midway Airport to San Francisco is April, where tickets cost $288 (return) on average. On the other hand, the most expensive months are February and March, where the average cost of round-trip tickets is $635 and $507 respectively.

Can I save money by flying with a layover from Chicago Midway Airport to San Francisco?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $372, prices are generally cheapest when you fly direct.

Good to know

Low seasonJanuary
Cheapest flight$133
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly with an average 23% increase in price.
Flight from Chicago Midway Airport to San Francisco

When to book flights from Midway to San Francisco

Are your dates flexible? Find out the best times to travel from Midway to San Francisco based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago Midway Airport to San Francisco flights

  • What is the cheapest flight from Chicago Midway Airport to San Francisco?

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to San Francisco was $133 for a one-way ticket and $270 for a round-trip.

  • Do I need a passport to fly between Chicago Midway Airport and San Francisco?

    No

  • Which airlines offer Wi-Fi service onboard planes from Chicago Midway Airport to San Francisco?

    American Airlines, JetBlue, Hawaiian Airlines, and Alaska Airlines offer inflight Wi-Fi service on the Chicago Midway Airport to San Francisco flight route.

  • Which aircraft models fly most regularly from Chicago Midway Airport to San Francisco?

    The Boeing 737 MAX 8 is the aircraft model that flies most regularly on the Chicago Midway Airport to San Francisco flight route.

  • On which days can I fly direct from Chicago Midway Airport to San Francisco?

    There are nonstop flights from Chicago Midway Airport to San Francisco on a daily basis.

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to San Francisco?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to San Francisco.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to San Francisco?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to San Francisco from Chicago Midway Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to San Francisco?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to San Francisco with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and SFO can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to San Francisco?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to San Francisco from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago Midway Airport to San Francisco

  • Looking for a cheap flight? 25% of our users found flights on this route for $184 or less one-way and $350 or less round-trip.

Prefer to fly direct from Chicago Midway Airport to San Francisco?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago Midway to San Francisco.
Find which airlines fly direct from Chicago Midway Airport to San Francisco Airport, which days they fly and book direct flights.

Direct departures

Chicago Midway to San Francisco

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

San Francisco to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Reviews of the top airline flying from Midway to San Francisco

 
See real verified KAYAK customer reviews for airlines flying from Chicago to San Francisco. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to San Francisco? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4295 reviews
8.6Crew
7.5Entertainment
8.1Boarding
8.0Comfort
7.0Food
Airline reviews

Plane was clean and comfortable. Flight attendants and gate staff were professional, friendly and efficient. Boarding and deplaning were orderly and efficient. All in all, the typical excellent Southwest experience.

10.0 ExcellentRobert, May 2026
LAS - SFO
Read more Southwest reviews

Plane was clean and comfortable. Flight attendants and gate staff were professional, friendly and efficient. Boarding and deplaning were orderly and efficient. All in all, the typical excellent Southwest experience.

Not having a five hour delay with little notice! The crew was very kind, though, and just as tired as we passengers were. The flight didn't depart until nearly 1 am...and no reason was ever given.

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

The Air hostess were very rude on my flight from Houston to Austin . Their regular communication itself felt a they are shouting at people.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

Boarding was easy. The seats are small and fairly uncomfortable

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

Mediocre. Boarding is now unpleasant. The employees, once friendly and nice, are now regularly speaking sternly to passengers, badgering them to do things right so they can take off on time and gate check bags because they don't have enough overhead bin space. The pretzel snack was crushed flat and broken into even smaller pieces, which happens frequently lately. Drink service was suspended before they reached my row.

Everything you need to know for your flight from Midway to San Francisco

Information on your arrival and departure airports