MDW - SFO

$126 Find Cheap Flights from Chicago Midway Airport to San Francisco - Compare and Save

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Everything you should know

Cheapest round-trip
$251
Typical prices: $295-$490
Southwest
Sun 10/14Sat 10/20
MDW - SFO • 1 stop
Cheapest non-stop
$265
Typical prices: $299-$518
Southwest
Fri 10/26Fri 11/2
MDW - SFO • Non-stop
Nonstop flights
You can fly direct with Southwest. Average duration is 4h 45m
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 49% compared to booking last minute.
Insights
Insights
When to travel
Cheapest • 28% price drop
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Cheapest • Avg $299 (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

Tue, Oct 13 - Tue, Oct 20
Southwest Logo
6:30 am - 11:30 amMDW  Chicago Midway-SFO San Francisco
7h 00m1 stop Los Angeles
Southwest Logo
12:15 pm - 10:15 pmSFO  San Francisco-MDW Chicago Midway
8h 00m1 stop Nashville Intl
$251Southwest
Wed, Oct 14 - Tue, Oct 20
Southwest Logo
6:25 am - 12:45 pmMDW  Chicago Midway-SFO San Francisco
8h 20m1 stop San Diego
Southwest Logo
2:30 pm - 11:50 pmSFO  San Francisco-MDW Chicago Midway
7h 20m1 stop Dallas Love Field
$251Southwest
Thu, Oct 8 - Mon, Oct 12
Frontier Logo
6:21 am - 5:55 pmMDW  Chicago Midway-SFO San Francisco
13h 34m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
11:59 pm - 2:35 pmSFO  San Francisco-MDW Chicago Midway
12h 36m1 stop Dallas/Fort Worth
$256Frontier
Sat, Oct 10 - Mon, Oct 12
Frontier Logo
3:30 pm - 10:25 pmMDW  Chicago Midway-SFO San Francisco
8h 55m1 stop Dallas/Fort Worth
Frontier Logo
11:59 pm - 2:35 pmSFO  San Francisco-MDW Chicago Midway
12h 36m1 stop Dallas/Fort Worth
$256Frontier
Sat, Oct 10 - Tue, Oct 13
Frontier Logo
3:30 pm - 10:25 pmMDW  Chicago Midway-SFO San Francisco
8h 55m1 stop Dallas/Fort Worth
Frontier Logo
11:59 pm - 2:35 pmSFO  San Francisco-MDW Chicago Midway
12h 36m1 stop Dallas/Fort Worth
$256Frontier
Wed, Nov 4 - Wed, Nov 11
Frontier Logo
6:16 am - 6:10 pmMDW  Chicago Midway-SFO San Francisco
13h 54m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
11:52 pm - 11:25 amSFO  San Francisco-MDW Chicago Midway
9h 33m1 stop Dallas/Fort Worth
$256Frontier
Sat, Oct 24 - Mon, Oct 26
Frontier Logo
6:21 am - 5:55 pmMDW  Chicago Midway-SFO San Francisco
13h 34m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
11:59 pm - 11:22 amSFO  San Francisco-MDW Chicago Midway
9h 23m1 stop Dallas/Fort Worth
$256Frontier
Sat, Oct 24 - Wed, Oct 28
Frontier Logo
3:30 pm - 10:25 pmMDW  Chicago Midway-SFO San Francisco
8h 55m1 stop Dallas/Fort Worth
Frontier Logo
11:52 pm - 11:25 amSFO  San Francisco-MDW Chicago Midway
9h 33m1 stop Dallas/Fort Worth
$256Frontier
Wed, Oct 28 - Wed, Oct 28
Frontier Logo
6:16 am - 6:10 pmMDW  Chicago Midway-SFO San Francisco
13h 54m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
11:52 pm - 11:25 amSFO  San Francisco-MDW Chicago Midway
9h 33m1 stop Dallas/Fort Worth
$256Frontier
Sat, Oct 10 - Mon, Oct 12
Frontier Logo
3:30 pm - 10:25 pmMDW  Chicago Midway-SFO San Francisco
8h 55m1 stop Dallas/Fort Worth
Frontier Logo
11:59 pm - 2:35 pmSFO  San Francisco-MDW Chicago Midway
12h 36m1 stop Dallas/Fort Worth
$256Frontier
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 from Chicago Midway Airport to San Francisco 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 start at $251. Prices are below average for this route right now, with typical round-trip fares ranging from $295 to $490. The lowest price found in the past 5 days was $251 on Southwest.

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

Wednesday is the cheapest day of the week to fly from Chicago Midway Airport to San Francisco, it is 15% cheaper than the average day. Sunday is the most expensive day with flight prices 31% higher than average. Based on deals found by KAYAK users in the last 12 months.

What is 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 $270 round-trip.
  • July ($447) and December ($417) are the most expensive months.
  • The price difference between flying in the cheapest and most expensive months is 65% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are prices 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 49% 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

$126
Best time to beat the crowds with an average 28% drop in price.
Most popular time to fly and prices are also 10% 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

Your Chicago Midway Airport to San Francisco flight questions, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines and booking questions.

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

    Among airlines operating Chicago Midway Airport to San Francisco flights:

    • Southwest: offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • What airlines are available from Chicago Midway Airport to San Francisco?

    Only Southwest operates flights between Chicago Midway Airport and San Francisco.

  • 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).

  • 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 and a checked bag in Economy Class
    • JetBlue: a cabin bag in Economy Class class

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

  • 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 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 $299 round-trip via Atlanta Hartsfield-Jackson (ATL), compared to $380 for nonstop.

  • 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 757-300 variants.

  • 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) - 72% of one-stop connections
    • Dallas/Fort Worth (DFW) - 8% of one-stop connections
    • Detroit Metropolitan Wayne County (DTW) - 8% of one-stop connections
    • San Diego (SAN) - 8% of one-stop connections

    Atlanta Hartsfield-Jackson (ATL) handles the largest share of one-stop connections on this route.

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

    Yes. Being flexible with your travel dates can save you up to 36% on the Chicago Midway Airport to San Francisco route. Wednesday is the cheapest departure day at $318 round-trip on average, while Sunday is the most expensive at $491, a difference of $173. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • 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 2 hours 15 minutes.

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

    Morning is the busiest departure period on Chicago Midway Airport to San Francisco flights, with 50% of flights leaving in that window. Night departures account for 50%, afternoon flights for 0%, and evening flights for 0%.

  • 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.

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

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

    • Earliest: departs at 9:45 am and lands at 2:30 pm
    • Latest: departs at 11:00 pm and lands at 3:45 am.

    The flight takes about 4h 45m.

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

    Last-minute fares on this route - booked within 2 weeks of departure - run 53% above the route average of $374. Book 12 weeks before departure for the lowest fares.

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

    A nonstop flight from Chicago Midway Airport to San Francisco takes 4h 45m, 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.

  • 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 $251 to $2,280. That means the highest observed fare was about 9x higher than the lowest one.

  • 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 $126, which is 45% below the typical average for this route.

  • How does Southwest’s on-time performance compare to other airlines on Chicago Midway Airport to San Francisco flights?

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

  • How do delay rates compare for morning and evening flights from Chicago Midway Airport to San Francisco?

    Afternoon flights have the fewest delays on this route. Delays tend to pile up throughout the day as one late flight pushes the next, so earlier departures are usually more reliable.

  • 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 04m 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 car rental options are available at San Francisco Airport (SFO)?

    San Francisco Airport (SFO) hosts 5 major car rental companies, with daily rates starting from around $15 for economy cars. Top options include:
    • Thrifty
    • Europcar
    • Dollar
    • Hertz
    • Fox

  • 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 $295 to $490, with an average of $374 over the past 12 months. Anything below $295 counts as a good deal.

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

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

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 can be flexible, aim for a Wednesday departure instead of Sunday. On this route, Wednesday flights average $318 - about $173 less than Sunday (35% 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 49% 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 $270 round-trip in that month - typically $177 less than the most expensive month, which is July (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 $299 round-trip on this route - about $81 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

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Tuesday

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Wednesday

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Thursday

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Friday

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Saturday

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Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

San Francisco to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

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Wednesday

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Thursday

Southwest

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Friday

Southwest

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Saturday

Southwest

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Sunday

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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