MDW - SFO

$53 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 8/19. 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 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
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Flights 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

Sat, Sep 27 - Sat, Oct 4
Southwest Logo
8:15 am - 10:50 amMDW-SFO
4h 35mnonstop
Southwest Logo
10:40 am - 4:45 pmSFO-MDW
4h 05mnonstop
$105Southwest
Find Deal
Wed, Sep 10 - Mon, Sep 15
Southwest Logo
11:45 am - 6:20 pmMDW-SFO
8h 35m1 stop
Southwest Logo
7:15 am - 1:20 pmSFO-MDW
4h 05mnonstop
$115Southwest
Find Deal
Sat, Sep 27 - Thu, Oct 2
Southwest Logo
9:50 am - 6:20 pmMDW-SFO
10h 30m2 stops
Southwest Logo
6:00 am - 12:05 pmSFO-MDW
4h 05mnonstop
$120Southwest
Find Deal
Wed, Aug 20 - Sat, Sep 6
Southwest Logo
5:10 pm - 9:40 pmMDW-SFO
6h 30m1 stop
Southwest Logo
1:00 pm - 11:25 pmSFO-MDW
8h 25m1 stop
$125Southwest
Find Deal
Wed, Sep 3 - Mon, Sep 8
Southwest Logo
6:40 am - 11:25 amMDW-SFO
6h 45m1 stop
Southwest Logo
7:15 am - 1:20 pmSFO-MDW
4h 05mnonstop
$129Southwest
Find Deal
Sat, Oct 25 - Fri, Oct 31
Southwest Logo
5:00 am - 11:15 amMDW-SFO
8h 15m1 stop
Southwest Logo
5:30 am - 11:30 amSFO-MDW
4h 00mnonstop
$130Southwest
Find Deal
Sun, Sep 28 - Sat, Oct 4
Southwest Logo
8:20 am - 10:55 amMDW-SFO
4h 35mnonstop
Southwest Logo
10:40 am - 4:45 pmSFO-MDW
4h 05mnonstop
$133Southwest
Find Deal
Wed, Sep 3 - Wed, Sep 10
Southwest Logo
10:45 am - 2:40 pmMDW-SFO
5h 55m1 stop
Southwest Logo
7:50 am - 4:55 pmSFO-MDW
7h 05m1 stop
$134Southwest
Find Deal
Wed, Oct 15 - Wed, Oct 22
Southwest Logo
2:45 pm - 5:15 pmMDW-SFO
4h 30mnonstop
Southwest Logo
6:30 am - 12:35 pmSFO-MDW
4h 05mnonstop
$135Southwest
Find Deal
Wed, Sep 3 - Wed, Sep 10
Southwest Logo
11:10 am - 5:45 pmMDW-SFO
8h 35m2 stops
Southwest Logo
5:55 am - 4:30 pmSFO-MDW
8h 35m1 stop
$139Southwest
Find Deal
Expert advice

Expert advice for your flight from Midway to San Francisco

 
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
Southwest

Enjoy two free checked bags up to 50 pounds each, ideal for travelers with lots of luggage.


Download the Southwest app for free in-flight messaging and entertainment streaming options.

Read more about Southwestby Blane Bachelor
Frontier

Choose the Economy Bundle for a carry-on bag and Standard seat selection without extra fees.


Opt for Premium seats for up to seven inches more legroom, enhancing comfort on longer flights.

Read more about Frontierby Stefanie Waldek
Our travel experts
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
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
Useful Info

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.

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 Friday 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 September, where tickets cost $248 (return) on average. On the other hand, the most expensive months are December and May, where the average cost of round-trip tickets is $468 and $448 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 $295, prices are generally cheapest when you fly direct.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure 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 average of all the values for each week.

To get a below average price on the flight from Chicago Midway Airport to San Francisco, you should book around 3 weeks before departure. For the absolute cheapest price, our data suggests you should book 15 weeks before departure.

Good to know

Low seasonFebruary
High seasonJuly
Cheapest flight$53
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly and prices are also 21% lower on average.
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 $53 for a one-way ticket and $105 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, 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 Airbus A321neo 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.

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

    The two airlines most popular with KAYAK users for flights from Chicago to San Francisco are Southwest and Delta. With an average price for the route of $434 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 $402 and an overall rating of 8.0.

  • 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 $198 or less one-way and $207 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 4 airlines serving 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 4250 reviews
8.0Comfort
8.1Boarding
7.0Food
8.6Crew
7.6Entertainment
Airline reviews

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

4.0 OkayAnonymous, Jun 2025MDW - LGA
Read more Southwest reviews

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

First time traveling on Southwest since bag fees were implemented. Usual good service. Just more expensive now.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

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

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

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

Great experience flying Southwest. The crew was really kind and helpful, and very friendly with our toddler.

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

Plane late from DC to Austin 30 minutes. Crew made up much of the time enroute to San Diego.

Fine, but how to board on SW versus othrr airlines, is just lame. Goood staff though and all was solid otherwise.

My flight was extremely cold. I had a jacket and a cover was left in each seat. The cover was extremely thin and I have a disability, fibromyalgia and arthrithis and AC air is the worst. I closed my vent and my husbands vent and it still was frigid. I asked the attendant if I could get another cover and she quickly almost dismissively and totally unconcerned stating, (I quote) (one per chair) and walked off so quickly that I didn't get a chance to explain to her that I literally have adisability. I didnt want to make a seen so I set on that flight for over 5 hours in pain, joints locking up and extremely uncomfortable. When my fibromyalgia flares up my joints not only ache but they will lock up also and it takes me days to get back to my regular self even though I take medication for it. I felt like it would not have hurt anyone at all for her to just give me an extra cover because I'm sure they have all types of medical issues in people that fly every day.

Not a "Delta" issue, but a JFK issue: We booked a connecting flight with 3 1/2 hours between to clearn immigration and customs. Our inbound flight (BCN to JFK) was on the taxiway 45 minutes which ate into our layover time. Immigtration was insanely quick with the CBP MPC app; however, clearing TSA (again, after we were ALREADY cleared in Spain on the inbound international flight) took over 95 minutes. This left us with 10 minutes before boarding the connecting flight (JFK to SAN) to walk to the far end of Terminal 4 and try to find food. We didn't find any food that could promise to serve us in under 10 minutes so we boarded the Delta flight after coming off a plance and an 8-hour flight knowing that we wouldn't be served any food on the next 5 1/2 hour flight. I feel like Delta needs to put pressure on the JFK TSA to open more screening stations (by our count, we saw only 5 scanners open and a line of - as we said - over 90 minutes. The insult is that we WERE ALREADY SCREENED through TSA, but as you come off one flight into the USA, you have to go through the whole process again. It seems like if you have a connecting flight, there should be a way to pass through immigration and customs without needing to return through TSA.

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

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

The entertainment and wifi mostly didn't work on this flight.

Terrible entertainment system - kept freezing and audio kept cutting out. Snacks were mediocre at best for a 5 hour flight.

I am still upset that my bag was lost on a recent trip to Rome ; we were inconvenienced and out €150 Euros ; delta has refused to reimburse us

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Seats are much much more comfortable than United, which is what I usually fly

If I pay extra for "comfort+" I expect leg room where I can stretch my legs. I was seated with an attendant's seat blocking my feet. Knee space was fine but my feet had less room than the non-"comfort+" seats. Also, don't go cheap on food when you have flights of 3+ hours. It's insulting.

Boarded plane and then delayed 1.5 hours while on the plane

My flight was delayed a very short period of time but they did not hold my connecting flight to San Diego, also through United. So they closed the doors before we got off our plane. They would only have to help the door open for another five to ten minutes. So I missed a court deadline for a manditory mediation settlement conference for my client. I had to get an associate to be there in person and be on the phone with him relaying what he needs to do the entire time. The court was very upset with me and so was my client. United cannot be trusted.

Really good 😊 the woman at the gate entrance was a little rude checking in our carry-on but i dont think she worked for the airline, she worked for the airport at sacramento, other than that amazing.

Boarding was mayhem. Late boarding by 15 minutes because of lack of staff (missing 1 flight attendant. We had to wait for an arrival of another plane before we could board). Flight was a little rough, but cannot blame on airlines.

United out of SFO is having issues with catering so none of our meals were loaded on the plane and no offer of compensation for our tickets purchased was offered.

A bit rush for transit. Food and entertainment are not available

The gate was too far away for the connecting flight

Generally good. The aisles have gotten narrower which can slow down boarding. Flight crew was great! Healthier complimentary snacks would be appreciated. Due to earthquake in San Francisco we had to circle in air space for a bit but then had a smooth landing. I laud the flight crew for their patience ;)

The agents was very rude and they charged me $50 for a carry-on bag saying that it was too big and then I saw someone going on a plane with the same size bag as me

For the most part united was a good experience, how ever when they came by with the snacks and water, they completely passed by my wife and I. As we were in separate rows. On a 5 hr flight we were not offered water

Terrible communication with weather delay, lost baggage, near impossible to reach customer service

My tickets got canceled on me by your site and I didn't have a flight. Then you kept sending me emails on the status of q flight I didn't have tickets for.

The delay was ridiculous because nary a word escaped from the gate attendant regarding our flight status. It was a complete joke.

I missed a flight because of a delay. I had to buy a new ticket through Southwest.

The crew was mostly okay. The flight attendant who answered our questions was curt and unhelpful unfortunately. He seemed upset and I understand having off days.

Flight was delayed one hour. Notification to the crowd waiting near the gate was terrible…announcements were unclear and very hard to hear and therefore understand. Frontier does NOT send texts to notify, only email. The reader board over the gate itself was NEVER updated to indicate the gate had been changed. It’s like a bunch of children are running things.

Very bad! No good service delayed my second connection flight

They canceled flight. Hard to believe there was even a plane incoming for us to get on

Plane was down graded and I lost my uncharged exit row with more leg room. No mention or offer of refund from podium. Flight attendant was nice to explain this happens often and that I could request a refund via online form submission. I did this and have heard nothing back.

Horrendous. I do not recommend Frontier. The passengers lack manners and decency, and the flight attendants lack professionalism. If I wasn’t in a bind to fly with 48 hours notice for a job interview, I would not have selected a flight with Frontier and I never plan to fly with them in the future.

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