MDW - SFO

$102 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 2/28. 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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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

Tue, Sep 30 - Tue, Oct 7
Southwest Logo
8:30 am - 2:40 pmMDW-SFO
8h 10m2 stops
Southwest Logo
3:00 pm - 12:25 amSFO-MDW
7h 25m1 stop
$212Southwest
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Tue, Sep 30 - Wed, Oct 1
Southwest Logo
8:30 am - 2:40 pmMDW-SFO
8h 10m2 stops
Southwest Logo
12:10 pm - 9:35 pmSFO-MDW
7h 25m1 stop
$213Southwest
Find Deal
Thu, Sep 25 - Mon, Sep 29
Frontier Logo
1:53 pm - 7:08 pmMDW-SFO
7h 15m1 stop
Frontier Logo
6:29 am - 3:53 pmSFO-MDW
7h 24m1 stop
$214Frontier
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Thu, Oct 30 - Mon, Nov 3
Frontier Logo
9:43 pm - 4:55 pmMDW-SFO
21h 12m1 stop
Frontier Logo
6:34 am - 10:11 pmSFO-MDW
13h 37m2 stops
$216Frontier
Find Deal
Thu, Sep 25 - Wed, Oct 1
Frontier Logo
1:53 pm - 7:08 pmMDW-SFO
7h 15m1 stop
Frontier Logo
8:00 am - 9:18 amSFO-MDW
23h 18m2 stops
$217Frontier
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Fri, Sep 26 - Sat, Oct 11
Frontier Logo
6:20 am - 9:21 pmMDW-SFO
17h 01m1 stop
Frontier Logo
10:23 pm - 11:46 pmSFO-MDW
23h 23m1 stop
$218Frontier
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Sat, Oct 4 - Sat, Oct 11
Southwest Logo
5:05 pm - 9:30 pmMDW-SFO
6h 25m1 stop
Southwest Logo
10:55 am - 10:35 pmSFO-MDW
9h 40m1 stop
$219Southwest
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Fri, Oct 3 - Tue, Oct 7
 Logo
4:48 pm - 12:16 amMDW-SFO
9h 28m1 stop
 Logo
8:00 am - 11:20 pmSFO-MDW
13h 20m2 stops
Sat, Oct 25 - Tue, Oct 28
Delta Logo
10:35 am - 5:54 pmMDW-SFO
9h 19m1 stop
Delta Logo
6:00 am - 5:43 pmSFO-MDW
9h 43m2 stops
$256Delta
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Sat, Oct 4 - Mon, Oct 6
Delta Logo
6:15 pm - 11:29 pmMDW-SFO
7h 14m1 stop
Delta Logo
12:35 am - 8:55 amSFO-MDW
6h 20m1 stop
$257Delta
Find Deal

Everything you should know

Top airlines
Southwest
Cheapest • from $212 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to book
3 weeks
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 31% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
November
Cheapest • 23% price drop
December
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$212
Overall average: $309
Southwest
Tue 9/30Tue 10/7
MDW - SFO • 2 stops
Cheapest non-stop
$227
Southwest
Thu 10/30Wed 11/5
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 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 November, where tickets cost $305 (return) on average. On the other hand, the most expensive months are December and July, where the average cost of round-trip tickets is $468 and $446 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.

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 $360 on average.

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, which saves you about 31% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 22 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$102
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly with an average 18% increase in price.
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 $102 for a one-way ticket and $212 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 757-300 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 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 $440 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 $191 or less one-way and $333 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 4248 reviews
8.0Comfort
8.6Crew
7.0Food
8.1Boarding
7.5Entertainment
Airline reviews

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

10.0 ExcellentKevin, Jul 2025MDW - PUJ
Read more Southwest reviews

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!

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.

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.

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

Seats were new and comfortable. Staff was fine. Missed my connection due to weather -which wasn’t their fault- but got no help at all. Gate staff sent me to customer service, which was and stayed unstaffed. Sign with QR code directed me to call or chat. Chat was useless. Call was returned after an hour. No itinerary offered by Frontier could get me home in less than 30 hours. Rebooked with another airline and got a partial refund that came to about 10 percent of what I paid to get home.

Finally a Frontier on time and efficient. I've had problems before with your airline, but this time everything went fine.

The experience was good. No frills but I got there safe and sound and on time.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

sluggish boarding and arrival procedures, fake nice flight attendants, and lots of delays.

Disaster. They lied every step of the way. We ended up being delayed due to crew and then allegedly abandoned the flight because of a curfew at LGA. No rebooking to LGA at any reasonable time. No hotel. No meal vouchers. Had to sleep in the airport and fly to Newark instead. Will never fly Frontier again.

What I expected, nickeled and dined and a frontier flight attendant loudly complained about her job and lack of communication as she headed to the gate on her cell phone. Not professional.

As every law enforcement agency I could imagine surrounded the plane and we didn’t disembark for 2 hours and then had to stick around for another hour to go get our personal belongings after leaving them behind and being bused away from the plane, it was scary and inconvenient. We were given no information as to why this was happening. Lack of communication with passengers was disappointing.

After boarding and un-boarding twice over 6+hours, the flight was canceled.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

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

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