MDW - SFO

$90 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 5/30. 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 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

 
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.

Recent round-trip flight deals from Midway to San Francisco

KAYAK's recommended round-trip deals from the most popular airlines that fly from Midway to San Francisco.
Discover the best prices for you by selecting your travel dates on KAYAK.
Frontier Logo
9:34 am - 10:33 pmMDW-SFO
14h 59m1 stop
Frontier Logo
11:50 pm - 11:26 amSFO-MDW
9h 36m1 stop
$198Frontier
Find Deal
Tue, May 13 - Tue, May 20
Frontier Logo
10:48 am - 10:22 pmMDW-SFO
13h 34m1 stop
Frontier Logo
9:59 pm - 12:24 pmSFO-MDW
12h 25m1 stop
$201Frontier
Find Deal
Sat, May 10 - Wed, May 14
Southwest Logo
5:15 am - 9:25 amMDW-SFO
6h 10m1 stop
Southwest Logo
7:45 pm - 5:00 amSFO-MDW
7h 15m1 stop
$207Southwest
Find Deal
Tue, Jun 24 - Tue, Jul 1
Frontier Logo
9:34 am - 10:33 pmMDW-SFO
14h 59m1 stop
Frontier Logo
6:35 am - 7:08 pmSFO-MDW
10h 33m1 stop
$208Frontier
Find Deal
Tue, May 13 - Thu, May 15
Frontier Logo
10:48 am - 10:22 pmMDW-SFO
13h 34m1 stop
Frontier Logo
6:35 am - 7:08 pmSFO-MDW
10h 33m1 stop
$211Frontier
Find Deal
Sat, May 10 - Mon, May 12
Southwest Logo
6:45 pm - 11:20 pmMDW-SFO
6h 35m1 stop
Southwest Logo
7:45 pm - 5:00 amSFO-MDW
7h 15m1 stop
$216Southwest
Find Deal
Tue, Jun 3 - Tue, Jun 10
Southwest Logo
8:00 pm - 12:15 amMDW-SFO
6h 15m1 stop
Southwest Logo
7:45 pm - 5:00 amSFO-MDW
7h 15m1 stop
$226Southwest
Find Deal
Thu, Jun 5 - Tue, Jun 10
Delta Logo
1:47 pm - 9:25 pmMDW-SFO
9h 38m1 stop
Delta Logo
12:52 am - 8:44 amSFO-MDW
5h 52m1 stop
$257Delta
Find Deal
Fri, Jun 13 - Sat, Jun 14
Delta Logo
7:25 pm - 11:51 pmMDW-SFO
6h 26m1 stop
Delta Logo
11:59 pm - 9:41 amSFO-MDW
7h 42m1 stop
$288Delta
Find Deal
Wed, Jun 4 - Tue, Jun 10
Delta Logo
7:21 pm - 11:37 pmMDW-SFO
6h 16m1 stop
Delta Logo
12:52 am - 8:44 amSFO-MDW
5h 52m1 stop
$298Delta
Find Deal
Fri, Jun 13 - Thu, Jun 19
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
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
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
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 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 Tuesday, 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 August, where tickets cost $243 (return) on average. On the other hand, the most expensive months are December and March, where the average cost of round-trip tickets is $469 and $402 respectively.

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 seasonMay
Cheapest flight$90
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly and prices are also 25% 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 $90 for a one-way ticket and $198 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 737-800 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 $441 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 $108 or less one-way and $218 or less round-trip.

Prefer to fly direct from Chicago Midway Airport 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
See more direct flights

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 4294 reviews
7.1Food
7.6Entertainment
8.6Crew
8.0Comfort
8.2Boarding
Airline reviews

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

10.0 ExcellentAnonymous, Apr 2025LGB - SMF
Read more Southwest reviews

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.

One of the crew performed a hilarious skit to accompany the standard instructions. Passengers enjoyed it so much they applauded at the end!

Excellent experience. WiFi worked on this leg of My trip

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.

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.

Only one side of the heafphone jack work. Crew was friendly and helpful.

Great. Flight departed early and arrived early. Deplaning and baggage claim ww were quick.

They separated our seats and moved us to the back of the plane. Hundreds of dollars and thousands of miles used and this was my platinum member experience.

AC barely worked on a 50 minute flight. It was very warm the whole flight. Flight was very bumpy and hard landing.

Got on the plane and then needed to deboard the plane because they didn’t have any pilots?

The flight was canceled two hours before departure, it took over five hours to rebook us on another flight.

Rough day of travel all the way around. Wrong info given to us multiple times and mistakes in their booking making our trip 10 hours longer than planned. I’m bummed because I fly Delta all the time and love them. Mistakes happen. Just bummed that this was a rare trip our whole family was traveling together.

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 ;)

headphone jack didnt work for the first flight and not much variety

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

Fantastic crew. Flight was delayed at last minute but we were given updates every 20 minutes and the crew was so friendly and considerate. I miss the touch screens on the back of the seats, wish they would bring that back though.

Beijing PEK to SFO. I had an economy seat on this flight. The seat comfort was acceptable. My main complaint is with the FA’s lack of personality and absence from servicing the plane, specifically restroom care (I wish I could share a pic of the restroom that I captured) and care of travelers—drink cart/availability of drinks. I'm amazed at the level of service on other International travel where a passenger is most often appreciated.

Awful. Worst airline I have ever been on. Crew were among the rudest people I have ever dealt with. United staff members were rude and disrespectful. My flight was delayed, causing me to miss a connecting flight. I understand things happen, but when staff start lying about what actually happened, that is when I have an issue. Just be honest, really it isn’t that hard. I’m being very honest with this review and I don’t find this difficult what so ever. In fact, because of United Airlines, my Christmas holiday was off to a really rocky start. As someone who has traveled across the world, it has only been United that I have had a truly awful experience.

Good flight. On time. Boarding and seating was easy. Crew were really friendly, yet professional. Bathroom (by cockpit) was small but serviceable. Some the seats were showing some notable wear & tear, but were comfy. Very happy UA customer. TY! 🤛🏽💗

The reps working at the airport counter were dumber than a second coat of paint.

My costume jewelry was stolen out of my bag. Got to airport and my bag weighed 45 pounds- 5 pounds over cost me $100 Long lines in tier one. No entertainment No WiFi no free drinks or snacks

Not very good. Paid in excess of $400 for assigned seating for my family and that was not provided. I want that money back.

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.

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….

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.

The plane was clean, the crew was friendly and helpful. It’s a low cost airline so there was no food, drinks or in flight entertainment but we didn’t expect any of these things. In the room for improvement department, they should install USB ports in seats to charge mobile devices.

I was surprised that all baggage, including carry on, were charged. Each additional bag went up in cost. Really disappointed in the additional costs.

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

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