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SFO - MDW

$44 Find cheap flights from San Francisco to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from San Francisco to Midway departing on 5/11. 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
0 bags
Sat 5/25
Sat 6/1

Search hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from San Francisco to Chicago, 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 San Francisco to Chicago, as well as popular online travel agencies
In the last 7 days travelers have searched 45,119,101 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

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Cheap flight deals from San Francisco to Midway (SFO-MDW)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from San Francisco to Midway 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 and deals for you by selecting your travel dates.
Choose your dates
3:58 pm - 10:09 pmSFO-MDW
4h 11mnonstop
4:28 pm - 6:57 pmMDW-SFO
4h 29mnonstop
$88Frontier
Find Deal
Sat, May 11 - Sat, May 18
3:58 pm - 10:09 pmSFO-MDW
4h 11mnonstop
4:28 pm - 6:57 pmMDW-SFO
4h 29mnonstop
$100Frontier
Find Deal
Wed, May 15 - Sat, Jun 1
3:58 pm - 10:09 pmSFO-MDW
4h 11mnonstop
9:10 pm - 10:07 pmMDW-SFO
26h 57m1 stop
$106Frontier
Find Deal
Wed, May 15 - Fri, May 17
9:03 am - 3:14 pmSFO-MDW
4h 11mnonstop
4:09 pm - 6:47 pmMDW-SFO
4h 38mnonstop
$108Frontier
Find Deal
Sat, Aug 17 - Sat, Aug 24
9:03 am - 3:14 pmSFO-MDW
4h 11mnonstop
4:09 pm - 6:47 pmMDW-SFO
4h 38mnonstop
$109Frontier
Find Deal
Sat, Aug 31 - Sat, Sep 7
9:11 am - 3:23 pmSFO-MDW
4h 12mnonstop
4:28 pm - 6:57 pmMDW-SFO
4h 29mnonstop
$110Frontier
Find Deal
Sat, May 25 - Sat, Jun 1
3:58 pm - 10:09 pmSFO-MDW
4h 11mnonstop
4:28 pm - 6:57 pmMDW-SFO
4h 29mnonstop
$111Frontier
Find Deal
Mon, May 13 - Sat, May 18
3:58 pm - 10:09 pmSFO-MDW
4h 11mnonstop
10:59 pm - 7:43 amMDW-SFO
10h 44m1 stop
$113Frontier
Find Deal
Sat, May 11 - Tue, May 14
9:06 pm - 8:31 amSFO-MDW
9h 25m1 stop
4:28 pm - 6:57 pmMDW-SFO
4h 29mnonstop
$114Frontier
Find Deal
Sat, May 11 - Sat, May 18
6:05 am - 4:55 pmSFO-MDW
8h 50m1 stop
7:10 pm - 11:25 pmMDW-SFO
6h 15m1 stop
$257Delta
Find Deal
Sat, May 18 - Wed, May 29

Flights from San Francisco to Midway - Travel Insights & Trends

Get data-powered insights and trends into flights from San Francisco to Midway 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 San Francisco to Chicago Midway Airport?

The average price of all flights from San Francisco to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.
For San Francisco to Chicago Midway Airport, Saturday is the cheapest day to fly on average and Friday is the most expensive. Flying from Chicago Midway Airport back to San Francisco, the best deals are generally found on Wednesday, with Tuesday being the most expensive.

What is the cheapest month to fly from San Francisco to Chicago Midway Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from San Francisco to Chicago Midway Airport, 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 San Francisco to Chicago Midway Airport is November, where tickets cost $163 on average. On the other hand, the most expensive months are March and June, where the average cost of tickets is $389 and $345 respectively.

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

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from San Francisco to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from San Francisco to Chicago Midway Airport, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 32 days before departure.

Which airlines provide the cheapest flights from San Francisco to Chicago Midway Airport?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the past 3 days, the cheapest one-way tickets to Chicago Midway Airport from San Francisco were found on Frontier ($44) and Delta ($118), and the lowest round-trip tickets were found on Frontier ($88) and Delta ($257).

Which airlines fly non-stop between San Francisco and Chicago Midway Airport?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from San Francisco to Chicago Midway Airport.
There is just one airline that flies from San Francisco to Chicago Midway Airport direct and that is Frontier. The best one-way deal found from Frontier for the route is $90.

How many flights are there between San Francisco and Chicago Midway Airport per day?

There is a maximum of 1 nonstop flight a day that takes off from San Francisco and lands in Chicago Midway Airport, with an average flight time of 4h 12m. The most common departure time is 9:00 am and most flights take off in the morning. Each week, there are 7 flights.

Which cabin class options are there for flights between San Francisco and Chicago Midway Airport?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There is only one cabin class option available for the route, which is Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from San Francisco to Chicago Midway Airport take?

The average nonstop flight takes 4h 11m, covering a distance of 1,849 miles.

What’s the earliest departure time from San Francisco to Chicago Midway Airport?

Early birds can take the earliest flight from San Francisco at 9:11 am and will be landing in Chicago Midway Airport at 3:23 pm.

What’s the latest departure time from San Francisco to Chicago Midway Airport?

If you prefer to fly at night, the latest flight from San Francisco to Chicago Midway Airport jets off at 3:58 pm and lands at 10:09 pm.

Good to know

Low season

January

High season

October

Cheapest flight

$44
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly and prices are also 32% lower on average.
Flight from San Francisco to Chicago Midway Airport

When to book flights from San Francisco to Midway

Are your dates flexible? Find out the best times to travel from San Francisco to Midway 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 San Francisco to Chicago Midway Airport flights

  • What is the cheapest flight from San Francisco to Chicago Midway Airport?

    In the last 3 days, the lowest price for a flight from San Francisco to Chicago Midway Airport was $44 for a one-way ticket and $88 for a round-trip.

  • Do I need a passport to fly between San Francisco and Chicago Midway Airport?

    No, a passport isn't needed to fly from San Francisco to Chicago Midway Airport. However, local authorities might ask for an official ID.

  • Which airports will I be using when flying from San Francisco to Chicago Midway Airport?

    When flying out of San Francisco you will be using San Francisco. You will be landing at Chicago Midway Airport, also known as Chicago Midway.

  • Which airlines offer Wi-Fi service onboard planes from San Francisco to Chicago Midway Airport?

    American Airlines, Alaska Airlines, Delta, and JetBlue offer inflight Wi-Fi service on the San Francisco to Chicago Midway Airport flight route.

  • Which aircraft models fly most regularly from San Francisco to Chicago Midway Airport?

    The Airbus A320neo is the aircraft model that flies most regularly on the San Francisco to Chicago Midway Airport flight route.

  • On which days can I fly direct from San Francisco to Chicago Midway Airport?

    There are nonstop flights from San Francisco to Chicago Midway Airport on a daily basis.

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

    The two airlines most popular with KAYAK users for flights from San Francisco to Chicago are Delta and Frontier. With an average price for the route of $344 and an overall rating of 8.0, Delta is the most popular choice. Frontier is also a great choice for the route, with an average price of $264 and an overall rating of 6.3.

  • How does KAYAK find such low prices on flights from San Francisco to Chicago Midway Airport?

    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 San Francisco to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from San Francisco to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from San Francisco 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 San Francisco to Chicago Midway Airport?

    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 Chicago Midway Airport with an airline and back to San Francisco with another airline. Booking your flights between San Francisco and MDW 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 San Francisco to Chicago Midway Airport?

    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 Chicago Midway Airport from San Francisco up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding a cheap flight from SFO to Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $65 or less one-way and $126 or less round-trip.

Prefer to fly non-stop from San Francisco to Chicago Midway Airport?

Find which airlines fly direct from San Francisco to Midway, which days they fly and book direct flights.

Nonstop departures

San Francisco to Chicago Midway

Monday

Frontier, Southwest

Frontier, Southwest

Tuesday

Frontier, Southwest

Frontier, Southwest

Wednesday

Frontier, Southwest

Frontier, Southwest

Thursday

Frontier, Southwest

Frontier, Southwest

Friday

Frontier, Southwest

Frontier, Southwest

Saturday

Frontier, Southwest

Frontier, Southwest

Sunday

Frontier, Southwest

Frontier, Southwest

See more direct flights

Nonstop returns

Chicago Midway to San Francisco

Monday

Frontier, Southwest

Frontier, Southwest

Tuesday

Frontier, Southwest

Frontier, Southwest

Wednesday

Frontier, Southwest

Frontier, Southwest

Thursday

Frontier, Southwest

Frontier, Southwest

Friday

Frontier, Southwest

Frontier, Southwest

Saturday

Frontier, Southwest

Frontier, Southwest

Sunday

Frontier, Southwest

Frontier, Southwest

See more direct flights
See more direct flights

Top 4 airlines serving from San Francisco to Midway

 
See real verified KAYAK customer reviews for airlines flying from San Francisco to Chicago. 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 San Francisco to Midway? 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
Alaska AirlinesOverall score based on 9110 reviews
8.6crew
7.3food
7.9comfort
8.2boarding
7.3entertainment
Airline reviews

I like that we took off on time and arrived a bit early. I like that I could gate check my bag and board early. I don't like how crowded the flight was. I had ok leg room, but could feel every move of the person next to me. And the aisles are very narrow. The gate and flight crews were terrific.

8.0 ExcellentKaren, Apr 2024SFO - JFK
Read more about Alaska Airlines reviews

I like that we took off on time and arrived a bit early. I like that I could gate check my bag and board early. I don't like how crowded the flight was. I had ok leg room, but could feel every move of the person next to me. And the aisles are very narrow. The gate and flight crews were terrific.

The flight was diverted and departed from San Jose instead of San Francisco. This could’ve been executed more smoothly because after arriving in San Jose it seemed like nothing was being processed correctly as needed for the gate agents to do their jobs well and the flight to leave on time

Excellent service and prices. I was not award of inflight entertainment.

Both flights from NYC to SFO were delayed more than an hour. No wifi, no screens/movies etc. The crew was nice.

They gave me a seat with extra leg room. But they didn't offer me anything to drink, just because it was an hour flight

flight delayed 2ish hours; status updates easily could have been conveyed in a more timely manner

Temperature was very cold. seat was uncomfortable bc headrest did not work properly - the earflaps would not move.

Alaska airlines is the best. Best customer service, crew, and value for money.

I have taken 4 Alaska flights in the past 3 weeks and every single flight was delayed. They give you a $12 voucher for airport food, sometimes too late, after you’ve already eaten. That might get you a bagel. Reservations, rentals, etc have to be cancelled with no repercussions. Will be avoiding Alaska if possible.

Window seat and a packed plane. A very uncomfortable flight.

There was a loud squeaky sound the whole time we were flying.

I usually have a positive experience with Delta. Complimentary upgrades are always nice!

I didn’t not like that I could not select my seat and ended up with the worse seat.

The landing was bad and the hostess came two times and i was sleeping but when she served the person that nexts to me I woke up and she didn’t even asked me if I need any drink or snacks two times!!!!

Plane was late because of a mechanical malfunction and the food listed as available was not. Flight attendants seem over worked and under paid. They just done seem happy. And that can be seen in their faces.

Waited 3 hours on a plane to de-ice due to manpower issues. Waited another hour and a half once we landed because of a gate issue. Missed my connections. Created. A total of 13 hours of delay.

Great, on time departure, friendly and accommodating crew, great leg room, Smith flight

Plane was turned around due to fog half way into the flight, Delta did not properly direct passengers to stay on same flight and instead failed to properly rebook on Alaska

Like most domestic flights in the US, you are basically on your own with this airline when it comes to food, so be sure to purchase meals and drinks ahead of time or expect to arrive starving and dehydrated (like I was).

You need to be a hacker to get the (Free) WiFi

Crew was great and did their best to make us comfortable and captain came out at the beginning to announce why the flight was delayed, weather situation up ahead, and kept us updated throughout the flight.

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

Awful. I got stuck next to a person carrying a dog and behind someone with a dog. People need to board these dogs downstairs. The cabin is crowded enough with your pets

Packed in like sardines, very uncomfortable. Sitting the aisle my shoulder was rammed into numerous times by rushing flight attendants. Also flight was very cold.

Airline did not explain reasons why flight was delayed two hours. Explanations were badly needed and rarely provided. Problem seemed to clearly be the airline’s fault and not the fault of the weather or airport.

Very uncomfortable seats and seat backs, and I am only 5’9”. Delayed due to crew issues, spent a long time with no ventilation. Teeny overhead bins. Wifi worked well. Arrived safely.

I was delighted that we were able to get on the 4:40 pm flight rather than our original booking at 6:55 pm!! Other than that, the flight was comfortable and landed early😊

The Palm Springs to Chicago O’Hare was on Time and Palm Springs airport is easier navigate. As our connection was only an approximately 50 minutes, we asked staff for insights for the Chicago airport in terms of transferring into the other terminal from which our flight left, and they were unhelpful. However, the United App was very helpful in terms of notifications and even providing directions. The Chicago to Detroit flight was significantly delayed which we all know does happen. However, there were very few updates or notifications as to why this was happening when we would actually arrive. It took nearly 30 minutes for bags to make it to baggage claim. We arrived nearly 1 hour late on a 40 minute flight.

Our flight was delayed many times throughout the day. The final delay was about 8 hours. I spent time in line to speak to someone at their understaffed desk, and also spent time waiting online and then chatting with a service rep. None of the United employees were any help at all. I desperately wanted to go get rest and possibly re-book my trip but I was denied any compensation or voucher for a hotel. I was repeatedly told it was not United's fault and therefore they had no compensation to offer. Overall, a cold and callous experience.

Paid WiFi was only available for a few minutes. Avoid at all costs.

There were 3 leg for the trip and each leg was delayed by 90 minutes or more. The boarding process takes forever with people waiting on the jetway even though most folks do not have carry-on. The whole process is poorly managed.

They cancelled the flight then did nothing to help us rebook. It was awful - I won’t fly with them again

The process of buying the ticket and navigating all the hidden charges that Frontier throws at you was a terrible experience. The actual airport experience and flying was fine.

The truck that was refueling the plane drove away with the hose still connected to the plane and ripped part of the plane off with it

Terrible. Seats are bad and the baggage policy is inconsistent

Better than I expected but I did pay for a seat and carry on bags ahead of time.

I hope to avoid flying with them in the future. First flight got cancelled then got stuck with a 13 hour layover in Denver. The process was long and frustrating to many people.

Flight was delayed on the runway for 40 minutes the crew did not even offer even water to passengers to compensate for the flight delayed. The flight was delayed due to aircraft mechanical issues. Worst customer service ever

The flight was delayed and I had to cancel because I would have missed my connection and there were no other flights for the next two days. They also lost my bag!!

My first time to fly Frontier and loved it! Boarding was super easy as we only had personal items. Crew was helpful and funny and the plane was clean. Pilot was also great at landing the plane smoothly.

Book cheap flights from San Francisco to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from San Francisco to Chicago found on KAYAK in the last 72 hours.
5/11Sat
nonstopFrontier
4h 11mSFO-MDW
$44
5/18Sat
nonstopFrontier
4h 12mSFO-MDW
$45
7/16Tue
1 stopDelta
8h 55mSFO-MDW
$118
7/20Sat
1 stopDelta
8h 55mSFO-MDW
$119
5/13Mon
3 stops
29h 25mSFO-MDW
$125
5/20Mon
2 stopsSouthwest
11h 45mSFO-MDW
$199
4/30Tue
3 stops
35h 51mSFO-MDW
$230
5/20Mon
3 stopsSouthwest
15h 55mSFO-MDW
$284
9/11Wed
2 stopsPorter Airlines
13h 22mSFO-MDW
$395
7/10Wed
2 stopsPorter Airlines
13h 22mSFO-MDW
$522

Search by stops

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Search by price

Last minute flights from San Francisco to Midway

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from San Francisco to Chicago that are departing in the next 10 days.
4/29Mon
multi-stopFrontier
8h 40mSFO-MDW
5/1Wed
nonstopFrontier
4h 39mMDW-SFO
$161
4/27Sat
multi-stopFrontier
9h 25mSFO-MDW
5/1Wed
nonstopFrontier
4h 39mMDW-SFO
$173
4/27Sat
nonstopFrontier
4h 11mSFO-MDW
5/1Wed
nonstopFrontier
4h 39mMDW-SFO
$174
4/29Mon
multi-stopFrontier
8h 40mSFO-MDW
5/7Tue
multi-stopFrontier
10h 44mMDW-SFO
$193
4/29Mon
multi-stopFrontier
8h 40mSFO-MDW
5/14Tue
multi-stopFrontier
12h 45mMDW-SFO
$198
4/29Mon
multi-stopFrontier
19h 07mSFO-MDW
5/7Tue
multi-stopFrontier
14h 49mMDW-SFO
$201
4/29Mon
multi-stopFrontier
8h 40mSFO-MDW
5/14Tue
multi-stopFrontier
14h 49mMDW-SFO
$203
4/29Mon
multi-stopFrontier
14h 02mSFO-MDW
5/8Wed
multi-stopFrontier
15h 58mMDW-SFO
$207
4/26Fri
multi-stopDelta
7h 52mSFO-MDW
4/30Tue
multi-stopDelta
9h 04mMDW-SFO
$383
4/25Thu
multi-stopDelta
7h 09mSFO-MDW
5/4Sat
multi-stopDelta
8h 27mMDW-SFO
$433

Search by stops

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San Francisco - Chicago Midway Airport Flights

Departure:

San Francisco (SFO)United States

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - San Francisco

Cabin classes:

$76