MDW - SFO

$158 Find Cheap Flights from Chicago Midway Airport to San Francisco - Compare and Save

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Everything you should know

Cheapest round-trip
$308
Typical prices: $296-$491
Frontier
Sat 12/22Fri 12/28
MDW - SFO • 1 stop
Cheapest non-stop
$319
Typical prices: $298-$506
Southwest
Sat 12/8Sat 12/15
MDW - SFO • Non-stop
Nonstop flights
You can fly direct with Southwest. Average duration is 4h 51m
Direct flights
+1
Direct flights
+1
Avoid delays
Most punctual • 57% on-time
Best time • Fewest delays
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 12 weeks in advance save around 51% compared to booking last minute.
Insights
Insights
When to travel
Cheapest • 37% price drop
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Cheapest • Avg $313 (round-trip)
Shortest trip • 6h 01m (one-way)
Insights
Insights
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Booking Insights
Flight Deals

Cheap Flights from Midway to San Francisco (MDW-SFO)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to San Francisco

Sat, Dec 19 - Thu, Dec 31
Frontier Logo
1:11 pm - 11:05 pmMDW  Chicago Midway-SFO San Francisco
11h 54m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
11:59 pm - 12:03 pmSFO  San Francisco-MDW Chicago Midway
10h 04m1 stop Dallas/Fort Worth
$308Frontier
Tue, Dec 22 - Mon, Dec 28
Frontier Logo
1:11 pm - 11:05 pmMDW  Chicago Midway-SFO San Francisco
11h 54m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
12:53 am - 12:10 pmSFO  San Francisco-MDW Chicago Midway
9h 17m1 stop Atlanta Hartsfield-Jackson
$308Frontier
Wed, Nov 25 - Tue, Dec 8
Frontier Logo
9:07 am - 4:38 pmMDW  Chicago Midway-SFO San Francisco
9h 31m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
11:44 pm - 11:33 amSFO  San Francisco-MDW Chicago Midway
9h 49m1 stop Atlanta Hartsfield-Jackson
$308Frontier
Tue, Dec 22 - Mon, Dec 28
Frontier Logo
1:11 pm - 11:05 pmMDW  Chicago Midway-SFO San Francisco
11h 54m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
12:53 am - 12:10 pmSFO  San Francisco-MDW Chicago Midway
9h 17m1 stop Atlanta Hartsfield-Jackson
$308Frontier
Sat, Dec 19 - Wed, Dec 30
Frontier Logo
1:11 pm - 11:05 pmMDW  Chicago Midway-SFO San Francisco
11h 54m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
12:53 am - 12:10 pmSFO  San Francisco-MDW Chicago Midway
9h 17m1 stop Atlanta Hartsfield-Jackson
$310Frontier
Tue, Dec 22 - Wed, Dec 30
Frontier Logo
1:11 pm - 11:05 pmMDW  Chicago Midway-SFO San Francisco
11h 54m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
12:53 am - 12:10 pmSFO  San Francisco-MDW Chicago Midway
9h 17m1 stop Atlanta Hartsfield-Jackson
$310Frontier
Wed, Nov 25 - Tue, Dec 8
Frontier Logo
9:07 am - 4:38 pmMDW  Chicago Midway-SFO San Francisco
9h 31m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
11:44 pm - 11:33 amSFO  San Francisco-MDW Chicago Midway
9h 49m1 stop Atlanta Hartsfield-Jackson
$310Frontier
Thu, Dec 24 - Mon, Dec 28
Frontier Logo
1:11 pm - 11:05 pmMDW  Chicago Midway-SFO San Francisco
11h 54m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
12:53 am - 12:10 pmSFO  San Francisco-MDW Chicago Midway
9h 17m1 stop Atlanta Hartsfield-Jackson
$310Frontier
Sat, Dec 5 - Sat, Dec 12
Southwest Logo
6:20 pm - 9:15 pmMDW  Chicago Midway-SFO San Francisco
4h 55mnonstop
Southwest Logo
11:35 pm - 6:00 amSFO  San Francisco-MDW Chicago Midway
4h 25mnonstop
$319Southwest
Wed, Dec 9 - Wed, Dec 16
Southwest Logo
9:05 pm - 11:55 pmMDW  Chicago Midway-SFO San Francisco
4h 50mnonstop
Southwest Logo
11:35 pm - 6:00 amSFO  San Francisco-MDW Chicago Midway
4h 25mnonstop
$329Southwest
Booking Insights

Price, demand and travel trends for Chicago Midway Airport to San Francisco flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

How much is a round-trip flight from Chicago Midway Airport to San Francisco?

Round-trip flights from Chicago Midway Airport to San Francisco typically range from $296 to $491. The lowest price found in the past 5 days was $308, on Frontier.

What's the cheapest day of the week to fly from Chicago Midway Airport to San Francisco?

Based on deals KAYAK users found in the last 12 months, Thursday is the cheapest day of the week to fly from Chicago Midway Airport to San Francisco. It’s 10% cheaper than the average day, while Sunday is the most expensive, with prices 23% higher.

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

•January is the cheapest month to fly from Chicago Midway Airport to San Francisco at $238 round-trip.
•November ($480) and July ($447) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 101% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are flights from Chicago Midway Airport to San Francisco the cheapest?

Flights from Chicago Midway Airport to San Francisco are cheapest 12 weeks before departure. Booking in this window typically costs about 51% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Key details for Chicago Midway Airport to San Francisco flights

Low season

January

Cheapest flight

$158
Beat the crowds with an average 28% drop in travelers.
The most popular month to fly with an average 33% increase in travelers.
One-way 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

Your Chicago Midway Airport to San Francisco flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • What are the earliest and latest flights from Chicago Midway Airport to San Francisco?

    These are the earliest and latest flight times currently scheduled from Chicago Midway Airport to San Francisco:

    • Earliest: departs at 9:55 am and lands at 2:46 pm
    • Latest: departs at 11:00 pm and lands at 3:51 am.

    The flight takes about 4h 51m.

  • What cabin classes can I book on flights from Chicago Midway Airport to San Francisco?

    Only Economy Class is available on flights from Chicago Midway Airport to San Francisco.

  • How long is a flight from Chicago Midway Airport to San Francisco?

    A nonstop flight from Chicago Midway Airport to San Francisco takes about 4h 51m, covering 1,849 miles.

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

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID or another TSA-accepted form of identification.

  • How much should I expect to pay for a Chicago Midway Airport to San Francisco flight?

    Round-trip flights from Chicago Midway Airport to San Francisco range from $296 to $491, with an average of $375 over the past 12 months. Anything below $296 counts as a good deal.

  • How expensive are last-minute Chicago Midway Airport to San Francisco flights?

    Last-minute fares on this route (booked within two weeks of departure) run 53% above the $375 route average. Book 12 weeks before departure for the lowest fares.

  • How much can I save by taking a layover when flying from Chicago Midway Airport to San Francisco?

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $313 round-trip via Atlanta Hartsfield-Jackson (ATL), compared to $382 for nonstop.

  • How does on-time performance compare across airlines flying from Chicago Midway Airport to San Francisco?

    Southwest is the only airline operating Chicago Midway Airport to San Francisco flights. 57% of its flights are on time.

  • What is the standard checked-bag allowance on flights from Chicago Midway Airport to San Francisco?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $45–$90 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • Which aircraft model is used most often on flights from Chicago Midway Airport to San Francisco?

    The Airbus A321-100/200 family is used most often on this route, operated mainly by American Airlines and United Airlines. Other aircraft seen on the route include Boeing 737 MAX 8 variants.

  • How are flight departures from Chicago Midway Airport to San Francisco spread across the day?

    Morning is most often the busiest departure period on Chicago Midway Airport to San Francisco flights, with 50% of flights leaving in that window. The rest depart at night.

  • Have flight prices from Chicago Midway Airport to San Francisco changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $308 to $2,117. That means the highest observed fare was about 7x higher than the lowest one.

  • Which airlines offer Wi-Fi on Chicago Midway Airport to San Francisco flights?

    JetBlue is typically the only airline on the Chicago Midway Airport to San Francisco route offering in-flight Wi-Fi. Pricing depends on fare class.

  • How are flight prices from Chicago Midway Airport to San Francisco looking right now?

    One-way fares from Chicago Midway Airport to San Francisco are currently lower than usual. Average one-way flight prices are about $162, which is 29% below the typical average for this route.

  • What car rental options are available at San Francisco Airport (SFO)?

    San Francisco Airport (SFO) hosts 5 major car rental companies, with daily rates averaging $63 for economy cars. Top options include:

    • Europcar
    • Thrifty
    • Dollar
    • Hertz
    • Fox

  • Which airports can I use when flying from Chicago Midway Airport to San Francisco?

    Flights from Chicago Midway Airport to San Francisco usually depart from Chicago Midway (MDW) and arrive at San Francisco (SFO).

  • What time of day has the fewest delays on flights from Chicago Midway Airport to San Francisco?

    Afternoon flights have the fewest delays on this route, while evening departures tend to have the most.

  • At what point is a flight considered delayed from Chicago Midway Airport to San Francisco?

    A flight is considered delayed when it departs 15 minutes or more after its scheduled time. This is the standard used by the US Department of Transportation and most airline industry reporting. On the Chicago Midway Airport to San Francisco route, 43% of flights were delayed in the past 3 months, with delays averaging 2h 12m.

  • Which airports do connecting flights from Chicago Midway Airport to San Francisco pass through?

    One-stop flights from Chicago Midway Airport to San Francisco most commonly connect through:

    • Atlanta Hartsfield-Jackson (ATL) - 79% of one-stop connections
    • Dallas/Fort Worth (DFW) - 7% of one-stop connections
    • Detroit Metropolitan Wayne County (DTW) - 7% of one-stop connections
    • Denver Intl (DEN) - 4% of one-stop connections

  • Can I save money by using flexible dates for flights from Chicago Midway Airport to San Francisco?

    Yes. Flexible dates can save you up to 27% on flights from Chicago Midway Airport to San Francisco. Thursday is the cheapest departure day at $341 round-trip on average, while Sunday is the most expensive at $464, a difference of $123.

    KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • What airlines fly from Chicago Midway Airport to San Francisco?

    Only Southwest currently operates flights between Chicago Midway Airport and San Francisco on a regular basis.

  • How much time can I save by choosing a different layover airport from Chicago Midway Airport to San Francisco?

    Flying via Denver Intl (DEN) gives the shortest average 1-stop total travel time at 6h 01m, compared with 7h 12m via Detroit Metropolitan Wayne County (DTW) and 8h 27m via San Diego (SAN).

  • What is the time difference between Chicago Midway Airport and San Francisco?

    San Francisco is 2 hours behind Chicago Midway Airport (Pacific Time vs Central Time). Plan for the time shift when scheduling connections or first-day activities.

  • What popular places can I visit in San Francisco?

    Some of the most popular sights in San Francisco are Fisherman's Wharf, Union Square and Moscone Center. These are among the most viewed places in San Francisco on KAYAK.

  • Which airlines offer free seat selection on Chicago Midway Airport to San Francisco flights?

    Only Southwest currently offers free seat selection on this route. Availability depends on fare class.

  • Which airlines offer extra legroom on Chicago Midway Airport to San Francisco flights?

    None of the airlines on this route currently offer extra legroom.

  • Which airlines include bags at no extra cost on Chicago Midway Airport to San Francisco flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • Southwest: a cabin bag in Economy Class class
    • JetBlue: a cabin bag in Economy Class class

    Bag allowance can vary by ticket type, cabin class, route and airline, so always check the fare details before booking.

Your guide to booking Chicago Midway Airport to San Francisco flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Thursday departure and avoid flying on Sunday. On this route, Thursday flights average $341, about $123 less than Sunday fares (27% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 12 weeks before you fly. On this route, that window historically saves about 51% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Chicago Midway Airport to San Francisco trip for January. Fares historically average $238 round-trip in that month - typically $242 less than the most expensive month, which is November (based on the last 12 months).
  • If you have the time, taking a 1-stop flight through Atlanta Hartsfield-Jackson Airport (ATL) can be cheaper than flying direct. The cheapest layover option averages $313 round-trip on this route - about $69 less than direct flights (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to San Francisco Airport.

    • Grand Hyatt At Sfo

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

More options for your flight from Midway to San Francisco

Complete your trip to San Francisco with a hotel stay or car rental