Southwest® flights from Chicago-Midway to San Francisco from $165

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Low fares from Chicago-Midway to San Francisco

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Chicago-Midway (MDW)to

San Francisco (SFO)
Depart: 02/16/2027

One-way

Basic

From
$165
Seen: 23 hrs ago

Chicago-Midway (MDW)to

San Francisco (SFO)
Depart: 12/09/2026

One-way

Basic

From
$165
Seen: 5 hrs ago

Chicago-Midway (MDW)to

San Francisco (SFO)
Depart: 12/08/2026

One-way

Basic

From
$165
Seen: 25 minutes ago

Chicago-Midway (MDW)to

San Francisco (SFO)
Depart: 01/06/2027

One-way

Basic

From
$165
Seen: 9 hrs ago

Chicago-Midway (MDW)to

San Francisco (SFO)
Depart: 12/15/2026

One-way

Basic

From
$165
Seen: 20 hrs ago

Chicago-Midway (MDW)to

San Francisco (SFO)
Depart: 01/12/2027

One-way

Basic

From
$165
Seen: 7 hrs ago
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Explore flights from Chicago-Midway to San Francisco

cmp-daily-histogram-bars-legend-min-price-aria-label $165
cmp-daily-histogram-bars-legend-max-price-aria-label $452
Displaying fares for November-2026
  • MDW–SFO, 11/14/2026: From $274
    14

    Sat

    NOV

  • MDW–SFO, 11/15/2026: From $274
    15

    Sun

  • MDW–SFO, 11/16/2026: From $274
    16

    Mon

  • MDW–SFO: cmp-view-offers-disclaimer. Find Offers
    17

    Tue

  • MDW–SFO, 11/18/2026: From $274
    18

    Wed

  • MDW–SFO, 11/19/2026: From $274
    19

    Thu

  • MDW–SFO, 11/20/2026: From $274
    20

    Fri

  • MDW–SFO, 11/21/2026: From $274
    21

    Sat

  • MDW–SFO, 11/22/2026: From $274
    22

    Sun

  • MDW–SFO: cmp-view-offers-disclaimer. Find Offers
    23

    Mon

  • MDW–SFO, 11/24/2026: From $274
    24

    Tue

  • MDW–SFO, 11/25/2026: From $274
    25

    Wed

  • MDW–SFO, 11/26/2026: From $274
    26

    Thu

  • MDW–SFO: cmp-view-offers-disclaimer. Find Offers
    27

    Fri

  • MDW–SFO, 11/28/2026: From $344
    28

    Sat

  • MDW–SFO, 11/29/2026: From $452
    29

    Sun

  • MDW–SFO, 11/30/2026: From $284
    30

    Mon

  • MDW–SFO: cmp-view-offers-disclaimer. Find Offers
    01

    Tue

    DEC

  • MDW–SFO, 12/02/2026: From $274
    02

    Wed

  • MDW–SFO, 12/03/2026: From $274
    03

    Thu

  • MDW–SFO, 12/04/2026: From $274
    04

    Fri

  • MDW–SFO, 12/05/2026: From $185
    05

    Sat

  • MDW–SFO, 12/06/2026: From $239
    06

    Sun

  • MDW–SFO: cmp-view-offers-disclaimer. Find Offers
    07

    Mon

  • MDW–SFO, 12/08/2026: From $165
    08

    Tue

  • MDW–SFO, 12/09/2026: From $165
    09

    Wed

  • MDW–SFO, 12/10/2026: From $185
    10

    Thu

  • MDW–SFO: cmp-view-offers-disclaimer. Find Offers
    11

    Fri

  • MDW–SFO, 12/12/2026: From $185
    12

    Sat

  • MDW–SFO, 12/13/2026: From $239
    13

    Sun

  • Range$165-$452

    Flight Details

    Departing from:
    Chicago Midway International Airport
    Arriving at:
    San Francisco International Airport
    Average flight time:
    4 hours 31 minutes
    Distance:
    1855 miles

    Explore San Francisco

    Explore one of the United States' most beautiful cities—San Francisco! From the San Francisco Bay Area's beautiful wine country to its sandy beaches, there is plenty to do on foot and in the water to make your trip one to remember. For fun outdoor activities to enjoy with your friends or the whole family, make sure to check out Fisherman's Wharf, the premiere San Francisco location for great seafood and beautiful views of the ocean. Go to the beach, have some delicious clam chowder, and shop some of San Francisco's best souvenir shops. You'll enjoy the great energy and the natural beauty of this bustling attraction.

    If you enjoy learning about U.S. history, San Francisco is a perfect city for you to visit. Rich with historical sites like the infamous Alcatraz Island, you'll get to enjoy taking a ferry ride to one of the West Coast's first lighthouses and forts. Of course, you might be more familiar with Alcatraz for the famous criminals it housed, such as Al Capone. Learn about the federal penitentiary's history and explore the island's wildlife. There is plenty of lush greenery to observe both on and off the island when you visit.

    Questions we hear the most

    The average flight time from Chicago (Midway) to San Francisco is 4 hours 31 minutes.
    There are 158 weekly flights from Chicago (Midway) to San Francisco on Southwest Airlines.
    Yes, Southwest flies nonstop from Chicago (Midway) to San Francisco once per day from Monday through Friday.
    Yes, Southwest flies nonstop from Chicago (Midway) to San Francisco once per day on Saturdays and Sundays.
    To find the lowest fares by day and time to fly Chicago (Midway) to San Francisco with Southwest, check out our Low Fare Calendar.
    You can rent a car at San Francisco International Airport book yours with your flight.
    Yes! Flights from Chicago (Midway) to San Francisco—or from here or there to anywhere—can be changed with no change fees. Fare difference may apply.
    Check the status of your upcoming Southwest flight.
    Check out the Southwest Airlines® Help Center for answers about everything Southwest.

    Popular Flights from Chicago-Midway