MDW - SFO

$126 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 3/1. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to 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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Flight 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

Thu, Dec 11 - Fri, Jan 9
Frontier Logo
6:15 am - 1:18 pmMDW-SFO
9h 03m1 stop
Frontier Logo
6:15 am - 8:02 pmSFO-MDW
11h 47m1 stop
$246Frontier
Find Deal
Fri, Dec 12 - Thu, Jan 8
Frontier Logo
6:15 am - 1:18 pmMDW-SFO
9h 03m1 stop
Frontier Logo
6:15 am - 8:02 pmSFO-MDW
11h 47m1 stop
$248Frontier
Find Deal
Thu, Feb 19 - Fri, Feb 20
Delta Logo
6:45 pm - 11:55 pmMDW-SFO
7h 10m1 stop
Delta Logo
12:40 am - 8:54 amSFO-MDW
6h 14m1 stop
$253Delta
Find Deal
Thu, Nov 27 - Sun, Dec 7
Frontier Logo
5:30 am - 8:47 pmMDW-SFO
17h 17m2 stops
Frontier Logo
6:30 am - 11:08 amSFO-MDW
26h 38m1 stop
$254Frontier
Find Deal
Thu, Feb 19 - Sat, Feb 21
Southwest Logo
5:00 am - 11:50 amMDW-SFO
8h 50m1 stop
Southwest Logo
6:55 am - 12:55 pmSFO-MDW
4h 00mnonstop
$263Southwest
Find Deal
Thu, Feb 19 - Fri, Feb 20
Delta Logo
6:45 pm - 11:55 pmMDW-SFO
7h 10m1 stop
Delta Logo
12:40 am - 8:54 amSFO-MDW
6h 14m1 stop
$273Delta
Find Deal
Mon, Nov 24 - Wed, Dec 3
Southwest Logo
8:10 am - 3:05 pmMDW-SFO
8h 55m1 stop
Southwest Logo
6:10 am - 12:15 pmSFO-MDW
4h 05mnonstop
$275Southwest
Find Deal
Mon, Nov 24 - Wed, Dec 3
Southwest Logo
8:10 am - 3:05 pmMDW-SFO
8h 55m1 stop
Southwest Logo
6:10 am - 12:15 pmSFO-MDW
4h 05mnonstop
$285Southwest
Find Deal
Thu, Feb 19 - Sat, Feb 21
Southwest Logo
8:15 am - 11:15 amMDW-SFO
5h 00mnonstop
Southwest Logo
6:55 am - 12:55 pmSFO-MDW
4h 00mnonstop
$290Southwest
Find Deal
Thu, Dec 18 - Wed, Dec 31
Delta Logo
10:49 am - 6:16 pmMDW-SFO
9h 27m1 stop
Delta Logo
12:10 am - 11:06 amSFO-MDW
8h 56m1 stop
$298Delta
Find Deal

Everything you should know

Top airlines
Frontier
Cheapest • from $246 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
February
Cheapest • 21% price drop
March
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$246
Overall average: $487
Frontier
Thu 12/11Fri 1/9
MDW - SFO • 1 stop
Cheapest non-stop
$275
Typical prices: $332-$357
Southwest
Fri 2/20Mon 2/23
MDW - SFO • Non-stop
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to San Francisco!
Booking Insights

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 Thursday, 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 Tuesday 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 February, where tickets cost $332 (return) on average. On the other hand, the most expensive months are December and October, where the average cost of round-trip tickets is $487 and $464 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 $370, prices are generally cheapest when you fly direct.

Good to know

Low seasonFebruary
Cheapest flight$126
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly and prices are also 2% 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 $126 for a one-way ticket and $246 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, Alaska Airlines, and Hawaiian 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 Boeing 737 MAX 8 is the aircraft model that flies most regularly on the Chicago Midway Airport to San Francisco flight route.

  • Which airline alliances offer flights from Chicago Midway Airport to San Francisco?

    Star Alliance is the only airline alliance operating flights between Chicago Midway Airport and San Francisco.

  • 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 United Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to San Francisco are Southwest and United Airlines. With an average price for the route of $457 and an overall rating of 8.0, Southwest is the most popular choice. United Airlines is also a great choice for the route, with an average price of $418 and an overall rating of 7.4.

  • 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 $155 or less one-way and $309 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 3 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 4240 reviews
7.0Food
8.1Boarding
8.0Comfort
7.5Entertainment
8.6Crew
Airline reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

8.0 ExcellentGreg, Oct 2025OAK - BUR
Read more Southwest reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Delays delays delays. Late taking off, late landing, wait for a gate, etc.

Connecting flight is on time and boarding was a breeze!

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

Very smooth checking in our luggage with a super pleasant SW agent. I enjoyed a fun entertaining movie.

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!

Flight from Rome to SFO was excellent compared To our flight to Europe from SFO. The food was much tastier. You can see how UNITED is skimping, though. Instead of getting something mid flight you had to ask for it. It was not automatically served. There was a cookie at the end of the arrival meal, for example that tasted like it just came out of a box. They used to serve a little container of nuts, now … a tiny container of nuts, mixed with pretzels. This was business class that you really have to pay for! But this is minor complaints compared to the overall. My major complaint is the position of the even numbered seats by the windows. You have to turn around to see your window & the positioning as some other controls are harder to get at. This is compared to the odd number seat that are perfectly aligned.

The food quality sucks. One must starve if they do not eat flesh Or wheat based products Some variety would be expected. The trivial amount of snacks and or food is inhumane

The internet service I paid for didn’t work at all and the flight crew was not very friendly.

Subject: Formal Complaint: Discriminatory and Unprofessional Conduct – Request for Immediate Action & Compensation Dear [Airline Customer Relations Team], I am writing to file a formal complaint regarding my recent travel experience with [Airline], which was by far the worst I have ever encountered. What occurred was not only unprofessional, but in several instances discriminatory, unsafe, and unacceptable. On the first leg of my trip, I arrived only four minutes past check-in. Instead of making any attempt to resolve the matter, your representative flatly denied me boarding and made me wait while she attended to passengers who arrived after me. By the time a manager intervened, it was too late to board, costing me time, money, and unnecessary frustration. The second leg of my trip (Chicago–San Francisco) raised even more serious concerns. From the outset, it was apparent that the staff—particularly two attendants—prioritized Caucasian passengers while dismissing African American and minority passengers. • When a Caucasian passenger in the exit row refused to comply with federal safety requirements, I, as a first responder, immediately offered to switch seats and assume the responsibility. My offer was blatantly ignored, and instead, a Caucasian passenger seated further up was chosen. This was discriminatory and deeply insulting, especially as I was actively de-escalating the situation that could have delayed the flight further. • During a lengthy tarmac delay of over 90 minutes, passengers were given conflicting and unreasonable instructions that created unnecessary distress and tension. • Throughout the flight, a visibly intoxicated passenger directly in front of me was disruptive, rude to others, failed to comply with seatbelt and electronic device rules, and yet faced no enforcement from the crew. In stark contrast, I was singled out for repeated compliance checks even though I was following every rule. This unequal treatment was so obvious that multiple passengers around me spoke up in my defense. This pattern of behavior demonstrated a clear lack of professionalism, disregard for passenger safety, and discriminatory treatment. I expect far better from an airline of your stature. As a paying customer subjected to this unacceptable treatment, I am formally requesting: 1. A full investigation into the conduct of the staff on both flights. 2. A written apology acknowledging the discriminatory and unprofessional behavior I endured. 3. Appropriate compensation for the distress, inconvenience, and mishandling of my travel. If this matter is not addressed promptly and thoroughly, I will have no choice but to escalate my complaint further, including filing with the U.S. Department of Transportation and sharing my experience through other channels. I trust [Airline] will take this complaint seriously and provide a timely resolution.

1. when we went to check in, our 2 first class seats had been CANCELED and the flight was sold out. This was done without our prior knowledge. It was all we could do to restore one first class seat for my wife and I flew economy. 2, Our flight home was scheduled to leave at 10:30 pm. Due to tsunami warnings, the roads were closed and our flight status was uncertain as to whether it would leave as scheduled. It was announced that it would now leave at 11:20 pm and the roads were now open since the tsunami had come and gone. We made a mad dash to the airport and checked in. Delays were announced at 12:30 pm, 1:30 am, 2:30 am and at 3:30 am it was canceled. Since this was a flight due to natural (tsunami) causes, there was no compensation. We were told to return at 1:00 pm the next day and our baggage would be kept on the plane since the same plane was going to leave at 1:00 pm. We had to return to our hotel for the rest of the night. The same plane did not leave at 1:00 pm and our baggage was gone! All in all, it was a miserable performance by UA. Information was hard to obtain and no one knew what was going on and what was going to happen. Hundreds of passengers slept on the floor, chairs, etc. No food and no water was made available to the passengers. It was a situation where UA could care less what was going on. As a one million mile flyer, I had not experienced anything like this before and it was hugely disappointing!

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.

Terrible. The canceled my entire flight when I requested a refund for a trip frontier canceled trip one way.

Boarding was on time and plane departed as scheduled. There are obviously no amenities (food, drink, entertainment) on Frontier, but there also didn't seem to be any issues with luggage space either.

Inbound plane was on time and flight departed on time with no issues while boarding.

I knew going into this that Frontier, being a low cost carrier, would be pretty bare bones and charge for most extras but this was made up for by the fact that the airplane was a reasonably new Airbus, every employee was great and best of all, Everett Washington is an amazing airport - thanks Frontier for flying there!!!

i was unable to check in the flight. refund requested

It was well done. It was my first time flying with them and I was nervous b/c I have heard of many cancelled and/or delray flights. Everything went smoothly.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

The single worst check in experience I could imagine. I’ll never do any business with Frontier or any affiliated company

Too many extra fees, uncomfortable, little leg room. Will not recommend this airline.

I think Frontier was very good at communication. Their app worked very well. Loading was great and the flight was nice and easy.

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

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