SFO - MDW

$109 Find Cheap Flights from San Francisco to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from San Francisco to Midway departing on 5/4. 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 Chicago Midway Airport

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

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Everything you should know

Cheapest round-trip
$245
Overall average: $382
Frontier
Sun 5/10Mon 5/11
SFO - MDW • 1 stop
Cheapest non-stop
$251
Typical prices: $351-$524
Southwest
Sat 5/2Tue 5/5
SFO - MDW • Non-stop
Top airlines
Cheapest • from $245 (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 07m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top layover airports
Cheapest • Avg $286 (round-trip)
Shortest trip • 6h 00m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 36% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 38% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
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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 Midway!
Flight Deals
Booking Insights
Flight Deals

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

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from San Francisco to Midway 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 San Francisco to Midway

Sun, May 10 - Mon, May 11
Frontier Logo
10:15 pm - 11:09 am
SFO
-
MDW
10h 54m
1 stop
Frontier Logo
3:07 pm - 11:04 pm
MDW
-
SFO
9h 57m
1 stop
$245Frontier
Tue, Apr 14 - Tue, Apr 21
Southwest Logo
5:25 am - 11:35 am
SFO
-
MDW
4h 10mnonstop
Southwest Logo
6:05 pm - 11:15 pm
MDW
-
SFO
7h 10m
1 stop
$247Southwest
Wed, May 27 - Sun, May 31
Frontier Logo
10:15 pm - 11:12 am
SFO
-
MDW
10h 57m
1 stop
Frontier Logo
6:00 am - 7:34 pm
MDW
-
SFO
15h 34m
1 stop
$249Frontier
Sat, Apr 25 - Sat, May 2
Frontier Logo
10:38 pm - 9:58 am
SFO
-
MDW
9h 20m
1 stop
Frontier Logo
6:00 am - 5:34 pm
MDW
-
SFO
13h 34m
1 stop
$250Frontier
Thu, Apr 23 - Tue, Apr 28
Southwest Logo
11:25 pm - 5:40 am
SFO
-
MDW
4h 15mnonstop
Southwest Logo
9:00 pm - 11:35 pm
MDW
-
SFO
4h 35mnonstop
$251Southwest
Thu, Apr 9 - Wed, Apr 15
Southwest Logo
5:15 am - 11:25 am
SFO
-
MDW
4h 10mnonstop
Southwest Logo
9:00 pm - 11:35 pm
MDW
-
SFO
4h 35mnonstop
$252Southwest
Thu, Apr 23 - Mon, Apr 27
Frontier Logo
11:16 pm - 12:30 pm
SFO
-
MDW
11h 14m
1 stop
Frontier Logo
6:00 am - 5:34 pm
MDW
-
SFO
13h 34m
1 stop
$253Frontier
Wed, May 6 - Mon, May 11
Southwest Logo
5:25 am - 11:35 am
SFO
-
MDW
4h 10mnonstop
Southwest Logo
9:45 pm - 12:20 am
MDW
-
SFO
4h 35mnonstop
$255Southwest
Sat, Apr 25 - Tue, Apr 28
Frontier Logo
10:38 pm - 9:58 am
SFO
-
MDW
9h 20m
1 stop
Frontier Logo
6:10 am - 5:34 pm
MDW
-
SFO
13h 24m
1 stop
$257Frontier
Tue, May 12 - Fri, May 15
Frontier Logo
10:40 pm - 10:02 pm
SFO
-
MDW
21h 22m
2 stops
Frontier Logo
3:07 pm - 11:04 pm
MDW
-
SFO
9h 57m
1 stop
$258Frontier
Booking Insights

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

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

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

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

If you are looking for a flight deal from San Francisco to Chicago Midway Airport, look for departures on Wednesdays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from Chicago Midway Airport, Wednesday is the cheapest day to fly and Monday is the most expensive.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from San Francisco to Chicago Midway Airport, 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 San Francisco to Chicago Midway Airport is January, where tickets cost $225 (return) on average. On the other hand, the most expensive months are December and October, where the average cost of round-trip tickets is $442 and $424 respectively.

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

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 $433, prices are generally cheapest when you fly direct.

How far in advance should I book a flight from San Francisco to Chicago Midway Airport?

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

To get a below average price on the flight from San Francisco to Chicago Midway Airport, you should book around 4 weeks before departure, which saves you about 36% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 10 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$109
Best time to beat the crowds with an average 38% drop in price.
Flight from San Francisco to Chicago Midway Airport

When to book flights from San Francisco to Midway

Are your dates flexible? Find out the best times to travel from San Francisco to Midway 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 San Francisco to Chicago Midway Airport flights

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

    In the last 3 days, the lowest price for a flight from San Francisco to Chicago Midway Airport was $109 for a one-way ticket and $245 for a round-trip.

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

    No, a passport isn't needed to fly from San Francisco to Chicago Midway Airport. However, local authorities might ask for an official ID.

  • Which airports will I be using when flying from San Francisco to Chicago Midway Airport?

    When flying out of San Francisco you will be using San Francisco. You will be landing at Chicago Midway Airport, also known as Chicago Midway.

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

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

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

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

  • Which airline alliances offer flights from San Francisco to Chicago Midway Airport?

    SkyTeam, and Star Alliance are the airline alliances operating flights between San Francisco and Chicago Midway Airport, with SkyTeam being the most commonly used for this route.

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

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

  • Which is the best airline for flights from San Francisco to Chicago, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from San Francisco to Chicago are Southwest and Delta. With an average price for the route of $400 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $358 and an overall rating of 7.9.

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

    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 San Francisco to Chicago Midway Airport.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from San Francisco 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 San Francisco to Chicago Midway Airport?

    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 Chicago Midway Airport with an airline and back to San Francisco with another airline. Booking your flights between San Francisco and MDW 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 San Francisco to Chicago Midway Airport?

    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 Chicago Midway Airport from San Francisco 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 San Francisco to Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $193 or less one-way and $337 or less round-trip.

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

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

Direct departures

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

Direct returns

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

Reviews of the top 4 airlines serving from San Francisco to Midway

 
See real verified KAYAK customer reviews for airlines flying from San Francisco to Chicago. 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 San Francisco to Midway? 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 4321 reviews
7.0Food
8.0Comfort
8.6Crew
7.5Entertainment
8.1Boarding
Airline reviews

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.

8.0 ExcellentTobin, Mar 2026
SJC - BUR
Read more Southwest reviews

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.

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

WiFi was not working and didn’t have a beverage service

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

The Southwest experience has definitely taken a dive from its early days. You can no longer deferentiate from other airlines. Air travel is too expensive. Southwest is no longer budget friendly. They have lost me as a loyal customer.

The charges were ridiculous for an hour flight and the turbulence was very scary.

The seats are now more narrow. I paid for front row the seats in the front are even more narrow than before.

The wifi on the plane is great. The only issue that I have is that I prefer an aisle seat and on my trips this week, I was either in the middle or window. If we can work to secure aisle seating, I will be thrilled. Nice trip.

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Great flight but super high price. Glad it was a business trip and not personal

I was in first class and literally the men behind me were so aggressively loud I moved myself to economy. This has become so common on Delta - people using audio without headphones, and men on 12am / late night flights drinking and yelling to talk to each other which prevents anyone around them from resting. Pretty crazy to have to move from first to economy (poorer service, less comfort...). Wild wild. Looking into other airlines.

There was an unruly family behind us that made the short flight miserable!!! The cabin crew did nothing to contain it.

Flight was delayed by 3-hours and their fix was… complimentary pretzels.

The crew, and fellow passengers, were super gracious and kind. There seemed to be plenty of bin space even though the plane was full. It’s nice to get a glass of wine with dinner in Premiere seating, and there was a lot of food.

Everything I mentioned earlier - the airbus was more comfortable indeed and the experience was further enhanced.

Flight delay was frustrating, also you cannot checkin online without delta app, web browser check-in throw errors

The plane was an older model, so it wasn’t as comfortable as others. The flight attendants were not helpful during onboarding. It was a full flight so there was chaos finding space for baggage.

Awesome! On time flight, early arrival, and a complimentary upgrade!

Got on the plane and sat there for an hour before departure.

Delta One is extraordinary. I fly business when somebody hires me. I just wonder why there is such a chasm between business class and the insanely inhumane and nonsensical coach. The seats are not large enough to fit even my tiny wife. We fly 10% of what we did because we don’t want to pay 5-10 k but for $400 it’s unbearable. It seems like the accountants took over and made stupid decisions. Screw in 20 extra seats and make it so unbearable that people fly 90% less. Just put the damn price up and put some proper chairs in. But business, yay.

Seats are uncomfortable. This has been a trend in the industry for decades. Trying to fit more seats on each plane to increase profits at the expense of the passenger.

Staff were good. My seat was in need of repair, but for a short flight was not problematic. Usual basic snack and drink setup that you'll find on any US carrier. Over, a decent, basic flight.

Flight delayed for more than 16 hrs and no effort was spent to provide an alternate

it was a very short flight so my expectations were low.

Very disappointing given gate agent behavior. Filed a formal complaint with United.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

Terrible. No customer service, no food, no drinks on a 6 hour premier economy booking.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

The flight crew where really good. Better then the crew from BNE to SFO

left on time, reasonable boarding process arrived early luggage came out quickly

Remind customers of the need to have passport or new ID for boarding.

The flight never took off and we spent 7 hours at the airport

Good for a budget airline! It was easy to get on, staff was really nice. Can’t say anything about the food or entertainment because it wasn’t available, which is fine.

It was ok. It was expensive to check 2 bags ($75.00 per bag), and then it took a long time to wait for shuttle to take us from one terminal to the terminal where the plane was taking off at LAX. And all of this for a flight where we had to pay for any food or drink that was not water.

This company socks. It's fraud. They canceled our flight yesterday, and today we were late because of a really long line at the check in bag. At the rebook station, there was ton of people. The workers were all rude. I am gonna make a report to FTC.

When I wanted to check in 3 hours prior to boarding time, the employees mentioned “a little over an hour delay” so I waited for an hour then I went to go look for food in the terminal and most people from that flight were in the same area looking for food. Finally I decided after food to check to see if it’s anytime closer and now it’s 2 mins until boarding closes?! What are you kidding me? I didn’t receive anything via sms about boarding now nor via email or on the intercom. I luckily made it through, barely, and then there’s no room for my carry on mind you I’m in the very first row so I had to place my purse in one further row back and my carry on sections down. Not sure who pays for better seats to get your stuff placed all over the plane but that was the worst experience I’ve ever had flying with anyone.

The single worst check in experience I could imagine. I’ll never do any business with Frontier or any affiliated company

Too many extra fees, uncomfortable, little leg room. Will not recommend this airline.

This airline sucks. They offer low rates then charge you for everything, the app does not work well, the seats are the most uncomfortable. Maintenance issues on the flight, and you still have to sit through their credit card commercials. People are nice enough but does not make up for overall poor experience.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

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

Information on your arrival and departure airports