SFO - MDW

$94 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 5/13. 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

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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Flights Deals

Cheap Flights from San Francisco to Midway

 
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.

Recent round-trip flight deals from San Francisco to Midway

KAYAK's recommended round-trip deals from the most popular airlines that fly from San Francisco to Midway.
Discover the best prices for you by selecting your travel dates on KAYAK.
Frontier Logo
11:50 pm - 1:34 pmSFO-MDW
11h 44m1 stop
Frontier Logo
2:12 pm - 10:22 pmMDW-SFO
10h 10m1 stop
$198Frontier
Find Deal
Sat, May 10 - Wed, May 14
Frontier Logo
2:03 pm - 2:48 pmSFO-MDW
22h 45m1 stop
Frontier Logo
2:44 pm - 12:09 amMDW-SFO
11h 25m1 stop
$200Frontier
Find Deal
Sat, May 17 - Sat, May 24
Frontier Logo
2:03 pm - 2:48 pmSFO-MDW
22h 45m1 stop
Frontier Logo
2:44 pm - 12:09 amMDW-SFO
11h 25m1 stop
$201Frontier
Find Deal
Sat, May 17 - Sat, May 24
Frontier Logo
2:03 pm - 2:48 pmSFO-MDW
22h 45m1 stop
Frontier Logo
2:44 pm - 12:09 amMDW-SFO
11h 25m1 stop
$202Frontier
Find Deal
Sat, May 17 - Sat, May 24
Southwest Logo
7:45 pm - 5:00 amSFO-MDW
7h 15m1 stop
Southwest Logo
7:00 pm - 11:10 pmMDW-SFO
6h 10m1 stop
$216Southwest
Find Deal
Tue, Jun 10 - Sat, Jun 28
Southwest Logo
6:35 pm - 5:20 amSFO-MDW
8h 45m1 stop
Southwest Logo
1:35 pm - 4:05 pmMDW-SFO
4h 30mnonstop
$217Southwest
Find Deal
Tue, Jun 3 - Thu, Jun 5
Southwest Logo
10:45 pm - 8:50 amSFO-MDW
8h 05m1 stop
Southwest Logo
5:40 pm - 12:10 amMDW-SFO
8h 30m1 stop
$226Southwest
Find Deal
Wed, Jul 9 - Mon, Jul 14
Delta Logo
12:52 am - 8:45 amSFO-MDW
5h 53m1 stop
Delta Logo
7:21 pm - 11:39 pmMDW-SFO
6h 18m1 stop
$257Delta
Find Deal
Mon, Jul 28 - Fri, Aug 1
Delta Logo
12:40 am - 8:36 amSFO-MDW
5h 56m1 stop
Delta Logo
7:25 pm - 11:51 pmMDW-SFO
6h 26m1 stop
$288Delta
Find Deal
Wed, May 28 - Mon, Jun 2
Delta Logo
12:40 am - 8:36 amSFO-MDW
5h 56m1 stop
Delta Logo
1:08 pm - 7:59 pmMDW-SFO
8h 51m1 stop
$297Delta
Find Deal
Fri, May 16 - Sat, May 24
Expert advice

Expert advice for your flight from San Francisco to Midway

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
Frontier

Frontier's Economy Bundle includes a carry-on bag and seat selection, ideal for budget travelers.


Frontier's Premium Bundle offers extra legroom and priority boarding, enhancing comfort and convenience.

Read more about Frontierby Stefanie Waldek
Southwest

Southwest offers two free checked bags, saving money for travelers with more luggage.


Download the Southwest app for free onboard Wi-Fi to stream entertainment and message.

Read more about Southwestby Blane Bachelor
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on Frontier

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor

Blane Bachelor

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Read more
Useful Info

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, Tuesday 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 September, where tickets cost $176 (return) on average. On the other hand, the most expensive months are December and March, where the average cost of round-trip tickets is $457 and $361 respectively.

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 3 weeks before departure. For the absolute cheapest price, our data suggests you should book 19 weeks before departure.

Good to know

Low seasonJanuary
High seasonJuly
Cheapest flight$94
Best time to beat the crowds with an average 30% 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 $94 for a one-way ticket and $198 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, Alaska Airlines, JetBlue, and Delta 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 Airbus A321neo 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 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 $392 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 $377 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 $183 or less one-way and $344 or less round-trip.

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

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
See more direct flights

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
Alaska AirlinesOverall score based on 9968 reviews
7.9Comfort
8.2Boarding
7.1Food
8.5Crew
7.1Entertainment
Airline reviews

No non-alcoholic drinks available except water and small apple juice cans.

8.0 ExcellentJohn, Apr 2025SFO - LAS
Read more Alaska Airlines reviews

No non-alcoholic drinks available except water and small apple juice cans.

The flight was delayed over two and a half hours thus causing me to miss my best friend’s funeral. All because the flight crew had to get more rest. That was the reason stated. I understand however very unfortunate. Glad everyone is well rested and resting in peace.

All good except both the outbound and return flights were delayed about 1 1/2 hrs.

Not great. My flight was canceled due to a mechanical problem and I could not get rebooked for the same day. I needed to get to my destination yesterday, not today. I was able to book with another airline but it was a layover and ultimately a 1 hour flight took me 12 hours. Normally I like Alaska much more than Southwest, but Southwest came through with a not terrible price for same day.

The plane was late arriving. The Alaska people did a great job of turning it around quickly and getting us off. We took off about 35 minutes after it reached the gate.

I liked the flight attendant named Tyler. He was charismatic and genuine. I like the pilot in my second flight, he was considerate to everyone’s feelings. I liked the people I sat beside. I like the plane size. I like Alaska airlines

Flight delay was inconvenient and exhausting getting in at 1 am. However the crew and lounge was very comfortable.

No complaints. Great service. A first class entry lane at boarding wouldn’t hurt.

I appreciate the priority for safety. I did not enjoy how the delays were handled.

Awful . Extra charge on my bags even after it was confirmed it wasn’t overweight.

It was a perfect flight in all aspects! Both legs!

Great flight, 47 passengers on a 180 seat plane. Stewardess was pleasant and cheerful.

I liked the crew member who gave flight instructions on "in case of a problem:. The seats are so small that only a young teenager could sit in middle seat.

Great flight staff. Ease of boarding. Overall, very uneventful and easy trip.

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

Employees were kind and funny, as always! Flight was late but no announcements were made for people with tight connections to help them transition quickly. No service due to turbulence.

I recently flew Southwest from San Jose to Honolulu. I was very impressed with the flight crew, especially the flight attendant in charge of the front of the plane. She came through the aisle at least five times for drinks and water, and two times for snacks. I have not seen such service since I flew first class. Also, for the first time, they gave us the correct baggage claim number, and the luggage came out quickly. I can't wait for Southwest to have assigned seating! I absolutely hate the Cattle Call boarding procedure and the mad dash to get seats and overhead bins. However, the boarding was efficient.

We had a nice flight. Boarding was easy, our seats were comfortable and the on board service was pleasant.

Service was great, boarding and exiting went smoothly, and the flight was very pleasant.

Was as expected. Crowed planes. Too many carryons delaying takeoff. But the ride only took an hour and saved me a lot of time SFO is a not a great airport.

Delta flight was on time, seats were comfortable, and crew was nice.

Thank you for not flipping the plane on the run way. You guys get a 5 star rating for the flight!!!

Boarding is, as it always is… horrible. Gate lice. Slow moving zones. Too many people with carry ons

It was terrible, if they ran flights on time it would make a big difference.

Delta seems to be improving in many areas, except they are super bad with the food available. Bring back normal food service on long flights.

I actually received a notification from kayak on email but not one by text from Delta when my departure gait changed and I almost missed my flight

New boarding doesn't make sense. Filling front first is slow.

Delta flight was great from the check in all the way to arrival. However, I had a very bad experience. I requested a wheelchair and the wheelchair employee that went to pick me up from the plane in Boston to bring me to the baggage claims told me I have to pay him. I was under the impression that it was a free service and I usually give tips but the person forced me to pay and since I said no because I was upset with his demand when my daughter walked in to pick me up he demanded payment from my daughter who paid him thinking maybe now it is a charged service.

Horrible. Grateful to be alive but spent 13 hours at airport only to return back to my familys house and flight changed to next day. They tried to fix a part on plane, had no back up plane and after 10 hours , reattempted the flight and it STILL wasn't fixed. We got a meal voucher and rescheduled flight but there should be some other compensation for the 15 hours spent in airport

5 hour delay. They blamed the weather but it was the computer issues they had been dealing with for days.

Compared with other carriers business class for an overnight was not worth the extra expense.

Easy to board. Flight was super crowded though so I didn't sleep well on that cross country red-eye flight. The aisles seem ot have gotten narrower and the seat smaller whn luggage and people are getting bigger so it would be AWESOME to have more space and breathing room in general ;)

Pilot Erika DeLong made us feel safe and at ease in a frankly scary time to be flying. Her warm smile and greeting and excellent command of the aircraft in foggy bumpy weather helped us all to calm our nerves and get us home safely.

Wish movie and music choices changed more often. Mostly same from a month or two ago when I last flew.

It was good. Just that the seats could not be reclined. The people behind were not ready to let the chairs be reclined

Plane left & arrived early- 5 Crew great. Wi fi - paid for 2, only 1 worked - so so. Waste of $. Coolie was good

There was no USB plug in my section of the plane. So I could not charge my phone. Also, there was no screen to watch movie or anything like that. Wish I had known that in advance, I would’ve brought my iPad.

Made all groups except 2 check despite ample bin space. Inflight WiFi and entertainment didn’t work most of the time.

Not enough room between rows and food was gross. $160 baggage charge?! Never again.

Excellent staff helping my 96 year old senior promptly with her oxygen needs

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.

They changed the timing , first delayed by 4 hours then went back to 40 mins late, we had to run back to airport to not miss our flight. This is ridiculous

No frills for sure. No gate announcements about flight delay, not even water to drink on the flight.

After waiting several minutes to be acknowledged by 3 employees on their phones, was told we had missed our flight because the doors were closed at that literal moment. Had they given any actual service or help while we were standing there we would have been on with time to spare. More than 10 people were turned away in this fashion claiming there was no way they could let us on the plane, even though it was still sitting connected to the terminal. After the desk agents let us know they didn't care about the situation we were forced to pay more than twice the price of our original tickets as no credits were given for the price of the "missed" flight. And the icing on the cake was after being treated poorly, fleeced for another few hundred dollars for new tickets? We waited on the next plane for 25 minutes passed the "doors closed" time, letting almost an extra dozen passengers on board. You're company has lazy, disinterested employees and your lack of any real help will ensure this was the first and last time we fly Frontier. Awful.

I loked walking out on the tarmac to board and no first class. I didn't like that they have no snacks or onboard wifi to bide your time.

It was a redeye flight, so every passenger just wanted to sleep, but through the entire flight, the flight crew made announcements over the loudspeaker at maximum volume every few minutes making sleep impossible. For example: it’s 2am, and the crew decides to give an extremely detailed announcement about snacks and beverages for sale. And 3am is the perfect time to wake up everyone with a lengthy announcement about how to get a coffee refill and how to take advantage of new offer from frontier for a credit card.

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

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