SFO - MDW

$102 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 12/5. 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

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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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, Oct 31 - Fri, Nov 7
Frontier Logo
9:55 pm - 2:57 pmSFO-MDW
15h 02m1 stop
Frontier Logo
1:37 pm - 9:11 pmMDW-SFO
9h 34m1 stop
$206Frontier
Find Deal
Thu, Nov 13 - Mon, Nov 17
Frontier Logo
6:33 pm - 11:30 amSFO-MDW
14h 57m2 stops
Frontier Logo
12:30 pm - 12:14 amMDW-SFO
13h 44m1 stop
$207Frontier
Find Deal
Mon, Sep 29 - Fri, Oct 3
Frontier Logo
11:00 pm - 3:58 pmSFO-MDW
14h 58m1 stop
Frontier Logo
5:15 pm - 9:21 pmMDW-SFO
30h 06m1 stop
$208Frontier
Find Deal
Sun, Sep 28 - Mon, Oct 20
Frontier Logo
11:57 pm - 1:11 pmSFO-MDW
11h 14m1 stop
Frontier Logo
6:24 pm - 12:14 amMDW-SFO
7h 50m1 stop
$210Frontier
Find Deal
Mon, Oct 13 - Mon, Oct 20
Frontier Logo
10:17 pm - 11:20 pmSFO-MDW
23h 03m2 stops
Frontier Logo
5:10 am - 4:00 pmMDW-SFO
12h 50m1 stop
$211Frontier
Find Deal
Thu, Oct 2 - Mon, Oct 20
Frontier Logo
11:57 pm - 8:52 pmSFO-MDW
18h 55m1 stop
Frontier Logo
6:24 pm - 12:14 amMDW-SFO
7h 50m1 stop
$212Frontier
Find Deal
Fri, Oct 3 - Fri, Oct 10
Frontier Logo
11:57 pm - 10:28 amSFO-MDW
8h 31m1 stop
Frontier Logo
5:10 am - 4:00 pmMDW-SFO
12h 50m1 stop
$213Frontier
Find Deal
Fri, Oct 17 - Mon, Oct 20
Frontier Logo
10:43 pm - 11:20 pmSFO-MDW
22h 37m2 stops
Frontier Logo
5:10 am - 4:00 pmMDW-SFO
12h 50m1 stop
$214Frontier
Find Deal
Mon, Oct 20 - Sun, Oct 26
Frontier Logo
6:34 am - 12:24 amSFO-MDW
15h 50m1 stop
Frontier Logo
6:24 pm - 2:22 pmMDW-SFO
21h 58m1 stop
$215Frontier
Find Deal
Tue, Nov 4 - Fri, Nov 7
Multiple Airlines Logo
5:28 pm - 12:41 pmSFO-MDW
17h 13m2 stops
Multiple Airlines Logo
8:55 am - 3:07 pmMDW-SFO
8h 12m1 stop
$230Multiple Airlines
Find Deal

Everything you should know

When to book
4 weeks
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 35% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
January
Cheapest • 39% price drop
April
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$206
Overall average: $374
Frontier
Fri 10/31Fri 11/7
SFO - MDW • 1 stop
Cheapest non-stop
$277
Typical prices: $368-580
Southwest
Wed 10/15Tue 10/21
SFO - MDW • Non-stop
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!
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 Thursdays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from Chicago Midway Airport, Thursday 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 $207 (return) on average. On the other hand, the most expensive months are July and December, where the average cost of round-trip tickets is $447 and $397 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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $292 on average.

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 35% 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$102
Best time to beat the crowds with an average 39% drop in price.
Most popular time to fly with an average 5% increase 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 $102 for a one-way ticket and $206 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, Alaska Airlines, Delta, and Hawaiian 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.

  • 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 Alaska Airlines?

    The two airlines most popular with KAYAK users for flights from San Francisco to Chicago are Southwest and Alaska Airlines. With an average price for the route of $397 and an overall rating of 8.0, Southwest is the most popular choice. Alaska Airlines is also a great choice for the route, with an average price of $280 and an overall rating of 8.0.

  • 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 $209 or less one-way and $317 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 5 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 4242 reviews
8.0Comfort
7.0Food
8.6Crew
8.1Boarding
7.5Entertainment
Airline reviews

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

10.0 ExcellentRobert, Sep 2025SFO - LAS
Read more Southwest reviews

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

No trays in our seats, we sat in first row, purchased a business class fare. Had to hold our drinks and snack in our hands. No plugs for our cell phones. Had to pay for it a drink cocktail each. Seats so uncomfortable.

Flight wasn’t even full, but too many carry-ons caused us to run out of bin space. New bag fee has folks who would usually check their bags carrying on. Watching Southwest morph into Spirit/Frontier is so sad to watch

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

My husband upgraded our seats and I don't know if it was due to the type of planet was or if they didn't upgrade our seats. We were supposed to be in I believe comfort seats and they were just as tight as any other seat- no leg room and we are very tall people but at least it wasn't extremely cold. My husband did put in a complaint about our seating because he paid extra and if we would have known that the space and the tightness would have been the same, we just would have gotten the emergency row emergency row seats that we normally get. We love Delta but both our flights coming home we're not good. Oh I forgot to mention that on our flight to Hawaii our luggage wheels got broke and we had to purse new luggage on vacation then we never had this problem so we didn't know protocol and reported it after we got home only for them to tell is we only had 24hrs to report the damage. Not sure what was going on with Delta this vacation trip.

Crew was excellent. Comfort seats not as nice as other kinds of planes.

It was a great flight and the stewards and stewardess were all kind and accommodating!! The seats were comfortable and entertainment screen excellent!

There are 4 flights in consecutive gates with about the same departure time. Two flights were boarding at the same time. One was delayed or boarding would be happening at the same time. I am not sure what Delta and LAX need to do to have a better layout at the end of Terminal 2

There was a security issue at the airport and we were unable to land. We circled endlessly and then landed at another airfield for fuel. We then circled the airport again, almost landed but didn’t fully touch down before circling again. I am thankful to the crew for keeping us safe- the issue was the airline and staff at the airport getting us seats on our connecting flights. That part was hours of searching for someone and getting in double my steps.

Most aspects were good however if they assign boarding zones they ought to enforce them or why bother? My luggage from SAN-JFK-MAD was lost in NY so I without my main bag for two days upon arrival in Spain. They were helpful in tracking it and eventually delivered it to my hotel. The flub was because of a delay upon arrival in NYC. I had booked 2 1/2 hours between flights but we had to hold on the taxiway for an hour after landing while waiting for a clear gate which likely caused the baggage error.

Excellent flight, the planes were newer, they did a nice job with boarding, great service overall.

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

737-800 in first class was pretty dumpy. Seat had an uncomfortable angle, storage under the seat was blocked so even my very modest backpack didn't fit, power outlet was flaky. Weird tiny seat pockets that couldn't hold a gallon ziploc bag, emesis bag missing, etc. etc. No in-flight service due to turbulence. Crew was excellent, boarding was smooth despite a full flight.

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.

Everything was great. Only thing that could’ve made it better was buy on board options for hot food, but the snacks were decent. The flight attendants were great. I had no complaints. I was able to make it to my destination safely

Horrific. They missed my connecting flight to San Diego. I didn’t get there until Monday at 9am when I had a mandatory court settlement conference scheduled at 6am since we had parties on the east coast. This caused many issues. All because United apparently forgot to hold the doors open until my flight landed that only had a 10 minute delay. This was the last flight to Southern California. So I couldn’t even rent a car to finish the trip. United cannot be trusted when traveling on specific days and times since weather didn’t have anything to do with the delays.

Very comfortable (upgraded to business class). The audio on my screen didn’t work, but I managed to play the audio through my phone while watching the screen.

Boarding seemed to be organized bedlam. For what ever reason, preboarding took longer than 20 minutes. Made the plane 20 minutes late taking off. Luckily we arrived on time. Flight crew seemed very friendly. Only slight turbulence.

The personnel were professional and friendly. The Boeing 737 Max 9 is too claustrophobic and was very warm at both airport gates, and still warm in the air.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

get E+, a must for 5 hours flight if you are tall

The first flight was better in terms of the aircraft.

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

Pretty good. The food was just mediocre, the boarding and crew were good.

My flight got switched and my prepaid bag didnt transfer over properly so I paid to check ANOTHER BAG. I was placed in a middle seat and it was just miserable. At least it was a bulkhead row so I had legroom. The flight just never seem3d to end

Was not able to watch most shows on the entertainment site. They would not load

On Wednesday, July 30 we were in mid flight from Manchester to Charlotte and we turned around because the right engine was malfunctioning. That was the last flight out of Manchester that night. I was rebooked for Thursday, which became a weather event Friday. There were no seats left on the flight from Manchester to Charlotte. Consequently I didn’t leave Manchester until Saturday morning and we flew to Chicago so to say the least my scheduled flight and return to Iowa was three days off and it messed with my business schedule. Consequently cash flow. I would like some sort of acknowledgment of this event.

Dreadful experience. Our flight was delayed more than 8 hours due to a maintenance issue and the assistance from rebooking was poor. I was travelling with a bad knee and needed assistance waited in one place more than 3 hours before someone came with a wheelchair. The woman next to me was a 91 year old great grandmother who had waited more than 4 hours. There were moments of support from the staff but it appeared as they were going against the direction of management. It was apathy, lack of ownership and dismissive responses with small moments of kindness and understanding typically from grey haired, female, veteran staff..

Couldn’t get the door on the plane to close leading to a nearly 2 hour delay. But, hey at least they didn’t cancel the flight.

Delayed flight, so I switched fights to SFO to Phoenix , Phoenix to DSM. Excellent service through American Airlines

The flight was fine and the crew awesome. The problem is ORD and AA. Computers went down, ORD fell apart and a 40 min flight turned into a 3 hour trip. Guess the answer is to not try and fly to ORD after noon. But, as I said, crew was awesome and did everything they could to lesson the flight time.

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.

I liked the turn-style feature at gate 209B at LAX. Very efficient process. The gate staff also made several, clearly directed announcements so I felt very informed.

The crew was delayed because they came on another flight that was delayed due to weather 10pm flight left at 1.30 am The airline made no effort to align alternate crew

The seats were awful, hard plastic covered in sheet vinyl. The airline tries to scam you into paying extra to get seat together when the flight wasn’t full. They were going to separate a family with young children but my wife who had a row to herself gave up her seat so the young mom could be with her young boys. I’m never giving this airline my money again.

It was a short flight so no food or entertainment….

Frontier had yet another flight cancellation. Have never made a complete round trip with this airline without at least one leg getting cancelled. Miserable flights - dirty, uncomfortable planes that apparently always have issues since I've had multiple delays and cancellations with them.

Flight was delayed 3 times, would have been nice to have received text message instead of email notifications. Frontier app wasn’t even updated accordingly, no gate number disclosed. No agent at front desk of gate to inform of delay. Very confused and left if the dark

The flight itself was ok and the pilot was very communicative. However, our flight was delayed for almost 3 hours, the gate was changed 3 times and there was no communication as we were waiting. The flight staff was overall a little crabby...I understand as they probably had a long day but we all did.

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