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 8/7. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 20% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flights Deals
Expert advice
Useful Info
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

Mon, Sep 8 - Thu, Sep 11
Frontier Logo
4:48 pm - 12:16 amMDW-SFO
9h 28m1 stop
Frontier Logo
10:19 am - 9:58 pmSFO-MDW
9h 39m1 stop
$121Frontier
Find Deal
Wed, Jul 30 - Wed, Aug 6
Frontier Logo
11:39 am - 9:23 pmMDW-SFO
11h 44m1 stop
Frontier Logo
11:30 pm - 1:29 pmSFO-MDW
11h 59m1 stop
$129Frontier
Find Deal
Wed, Aug 13 - Mon, Aug 18
Frontier Logo
11:39 am - 9:23 pmMDW-SFO
11h 44m1 stop
Frontier Logo
10:29 pm - 9:02 amSFO-MDW
8h 33m1 stop
$136Frontier
Find Deal
Thu, Aug 21 - Sat, Aug 23
Frontier Logo
3:52 pm - 10:50 pmMDW-SFO
8h 58m1 stop
Frontier Logo
10:29 pm - 10:08 amSFO-MDW
9h 39m1 stop
$141Frontier
Find Deal
Tue, Aug 12 - Thu, Aug 14
Frontier Logo
11:39 am - 8:47 pmMDW-SFO
11h 08m1 stop
Frontier Logo
11:30 pm - 11:49 amSFO-MDW
10h 19m1 stop
$144Frontier
Find Deal
Wed, Jul 23 - Wed, Jul 30
Frontier Logo
11:39 am - 9:23 pmMDW-SFO
11h 44m1 stop
Frontier Logo
11:30 pm - 1:29 pmSFO-MDW
11h 59m1 stop
$145Frontier
Find Deal
Fri, Aug 22 - Sun, Aug 24
Frontier Logo
10:58 am - 8:51 pmMDW-SFO
11h 53m1 stop
Frontier Logo
10:29 pm - 10:08 amSFO-MDW
9h 39m1 stop
$151Frontier
Find Deal
Sat, Aug 16 - Mon, Aug 18
Frontier Logo
2:44 pm - 11:25 pmMDW-SFO
10h 41m1 stop
Frontier Logo
10:29 pm - 9:02 amSFO-MDW
8h 33m1 stop
$152Frontier
Find Deal
Thu, Sep 4 - Sun, Sep 7
Southwest Logo
11:10 am - 1:45 pmMDW-SFO
4h 35mnonstop
Southwest Logo
1:15 pm - 7:20 pmSFO-MDW
4h 05mnonstop
$179Southwest
Find Deal
Sat, Aug 23 - Sat, Aug 30
Southwest Logo
8:15 am - 10:50 amMDW-SFO
4h 35mnonstop
Southwest Logo
10:20 am - 4:25 pmSFO-MDW
4h 05mnonstop
$188Southwest
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 Wednesday 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 $121 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 $436 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 $448 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 $179 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 4266 reviews
8.2Boarding
7.6Entertainment
8.0Comfort
7.0Food
8.6Crew
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

We’ve all seen the YouTube vids of out of control passengers. But this was an instance of a highly aggressive, bully flight attendant. Yelling in the face of a vet with PTSD who was texting their family. And no , we had not yet been instructed to put our phones in airplane mode. My suggestion is that you should pay whatever difference there is in order to avoid Frontier airlines. Additionally, after 3hrs trying to get customer service frontier offered a $25 voucher. I declined. This experience was so traumatic. To be verbally assaulted and abused by a flight attendant that has the power to say “boo” and I miss my flight ( which was to a family member’s funeral ). Frontier is unsafe and I cannot impress enough how much I discourage anyone ( esp those with any kind of disability like PTSD ) flying on Frontier.

My flight was delayed by two hours which made it so that I would miss my layover flight. I stood in line for customer service for over an hour and when I reached the agent she told me to scan a QR code and it'll give me options. I wasn't offered any help, guidance or compensation, only told that I have options but that I had to figure it all out myself. I was refunded part of the trip and had to buy an expensive same day ticket from another airline in order to get home. I will never fly Frontier again.

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

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.

The seats were hard molded plastic covered in plastic vinyl. And the scam to charge people extra to sit together. Don’t they know we can just ask someone to trade seats. And watching the staff separate young children from parents… super classy. We had to guilt them into offering up our seats. This companies policies suck. Don’t give them your money.

Everything went as planned. Crew was great. Seats were still not that comfortable.

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

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

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.