SFO - MDW

$113 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 3/3. 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
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Everything you should know

Cheapest round-trip
$249
Overall average: $271
Frontier
Fri 2/27Mon 3/9
SFO - MDW • 1 stop
Cheapest non-stop
$250
Typical prices: $302-$677
Southwest
Sat 2/21Mon 2/23
SFO - MDW • Non-stop
Top airlines
Frontier
Cheapest • from $249 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to book
4 weeks
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 43% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
January
Cheapest • 37% price drop
April
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 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

Fri, Feb 27 - Mon, Mar 9
Frontier Logo
3:18 pm - 11:41 pm
SFO
-
MDW
6h 23m
1 stop
Frontier Logo
6:05 am - 7:14 pm
MDW
-
SFO
15h 09m
1 stop
$249Frontier
Sat, Feb 21 - Mon, Feb 23
Southwest Logo
6:55 am - 12:55 pm
SFO
-
MDW
4h 00mnonstop
Southwest Logo
8:15 am - 11:15 am
MDW
-
SFO
5h 00mnonstop
$250Southwest
Thu, Mar 5 - Sat, Mar 7
Frontier Logo
6:15 am - 9:12 pm
SFO
-
MDW
12h 57m
2 stops
Frontier Logo
6:00 am - 7:20 pm
MDW
-
SFO
15h 20m
1 stop
$251Frontier
Sat, Feb 21 - Fri, Mar 6
Delta Logo
6:05 am - 4:14 pm
SFO
-
MDW
8h 09m
1 stop
Delta Logo
1:29 pm - 6:36 pm
MDW
-
SFO
7h 07m
1 stop
$252Delta
Mon, Feb 23 - Wed, Mar 11
Frontier Logo
3:08 pm - 11:44 pm
SFO
-
MDW
6h 36m
1 stop
Frontier Logo
11:25 am - 12:28 am
MDW
-
SFO
15h 03m
2 stops
$253Frontier
Fri, Feb 20 - Fri, Mar 6
Frontier Logo
3:18 pm - 11:41 pm
SFO
-
MDW
6h 23m
1 stop
Frontier Logo
6:05 am - 7:14 pm
MDW
-
SFO
15h 09m
1 stop
$254Frontier
Thu, Feb 19 - Sun, Feb 22
Frontier Logo
8:05 am - 10:37 pm
SFO
-
MDW
12h 32m
2 stops
Frontier Logo
9:04 pm - 10:01 pm
MDW
-
SFO
50h 57m
2 stops
$255Frontier
Thu, Mar 5 - Mon, Mar 9
Frontier Logo
6:15 am - 9:12 pm
SFO
-
MDW
12h 57m
2 stops
Frontier Logo
6:05 am - 7:14 pm
MDW
-
SFO
15h 09m
1 stop
$257Frontier
Mon, Mar 2 - Sat, Mar 7
Southwest Logo
6:25 am - 12:25 pm
SFO
-
MDW
4h 00mnonstop
Southwest Logo
9:40 pm - 12:20 am
MDW
-
SFO
4h 40mnonstop
$258Southwest
Fri, Feb 27 - Thu, Mar 12
Frontier Logo
3:18 pm - 11:41 pm
SFO
-
MDW
6h 23m
1 stop
Frontier Logo
6:05 am - 7:14 pm
MDW
-
SFO
15h 09m
1 stop
$259Frontier
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 Tuesdays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from Chicago Midway Airport, Saturday 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 $309, 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 43% 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$113
Best time to beat the crowds with an average 37% drop in price.
Most popular time to fly and prices are also 10% lower on average.
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 $113 for a one-way ticket and $249 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, JetBlue, Delta, 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 $396 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 $338 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 $154 or less one-way and $339 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 4267 reviews
8.1Boarding
7.0Food
8.0Comfort
7.5Entertainment
8.6Crew
Airline reviews

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.

8.0 ExcellentJoseph, Jan 2026
LGB - PHX
Read more Southwest reviews

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

The seats were comfortable, and the boarding process was pretty smooth.

3 hour delay. Had to change plans and was still delayed.

We got exit row seats both flights. Everything was running on time

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

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.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

Delta’s staff is unmatched. From the gate agents, to the pilots, to the flight attendants… all top of the industry.

The flight was delayed for about 2 hrs. Other than it, it was good.

I am extremely disappointed that delta internal pilot manuals now refer to the Gulf of Mexico as the “gulf of America”. You can bow down to the Orange turd on your own. I will never fly delta again

No lunch on a x-country flight scheduled for 10:50 am departure, arrived 5+ hrs later. That requires a black box label before you pay for the tickets. Worst, when I checked in online, it's specifically said that lunch was served on his flight for economy Plus passengers.

Our flight from SFO to MSP was right on time on 11/15/2025. No delays. As we approached MSP at about 8 pm, we circled in the air until 8:40 pm so I don't call that efficient for MSP. I think the captain should announce the delay and why. (as if we all don't know that we are just circling around the area, slowing down, speeding up, slowing down.) Thank you. Marilyn Fischer

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

The flight used a B767 with a very old interior from before 2014. The entertainment system did not work at all during the flight despite attempts to reset the system. It was like they flew this route just to be competitive.

Delayed flight (1hour) plus a long layover after an overnight flight with no backup plane available.

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

Pushed back only to get deplaned due to a tire damaged by ground crew. They did at least go pretty fast. The bathrooms should be banned under the Geneva convention. No room to even sit straight on the toilet. The under-seat entertainment units block what little leg room there is.

United airlines has the best customer experience from booking to arrival. I always fly United airlines. The mileage program is excellent

Older aircraft, no meal, only food was for purchase. Not impressed United.

Not pleasant trip cross country when the entertainment and WiFi system not working. No entertainment for entirety of route. Staff was rather nonchalant in that they dismissed the problem due to age of plane. It would have been nice to know this up front so I could have come prepared to read or download movies before boarding Coincidentally or not, there was a similar issue with the entertainment system on my previous flight I took on my fist leg of the trip. There are no seat TVs, so you must rely on the app when it works. United can do better. Also, what use it it to pay for boarding group 2 when half of the passengers are in the same line as you?

Premium Plus is a really good idea for longer flights

Stuck on tarmac for two hours plus a 5.5 hour flight. Rude flight attendant. And no meals, not even for purchase!

I learned that seating towards the end of plane that a line forms for the restroom and people use your chair as a hand railing, bumping your seat consistently. I was seated in the aisle. I think that next time if I am towards the back row I would want to sit in the middle or window seat.

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.

We were delayed three times ,and that destroyed my plans, and reservations

Cancelled flight after I arrived at airport after 75 min drive and parking. Next flight was 4 days in the future. Had to scramble and buy a much more expensive flight on another carrier.

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

Information on your arrival and departure airports