Southwest® flights from Oakland to Chicago-Midway from $160

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Low fares from Oakland to Chicago-Midway

$

Oakland (OAK)to

Chicago-Midway (MDW)
Depart: 12/12/2026

One-way

Basic

From
$160
Seen: 22 hrs ago

Oakland (OAK)to

Chicago-Midway (MDW)
Depart: 12/01/2026

One-way

Basic

From
$160
Seen: 21 hrs ago

Oakland (OAK)to

Chicago-Midway (MDW)
Depart: 01/06/2027

One-way

Basic

From
$160
Seen: 12 hrs ago

Oakland (OAK)to

Chicago-Midway (MDW)
Depart: 01/20/2027

One-way

Basic

From
$160
Seen: 9 hrs ago

Oakland (OAK)to

Chicago-Midway (MDW)
Depart: 12/16/2026

One-way

Basic

From
$160
Seen: 8 hrs ago

Oakland (OAK)to

Chicago-Midway (MDW)
Depart: 12/02/2026

One-way

Basic

From
$160
Seen: 16 hrs ago

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Explore flights from Oakland to Chicago-Midway

Nov 2026
From$198*
Seen: 12 hrs ago
One Way/Basic
Dec 2026
From$160*
Seen: 7 hrs ago
One Way/Basic
Jan 2027
From$160*
Seen: 6 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $160
cmp-daily-histogram-bars-legend-max-price-aria-label $399
Displaying fares for November-2026
  • OAK–MDW, 11/10/2026: From $274
    10

    Tue

    NOV

  • OAK–MDW, 11/11/2026: From $274
    11

    Wed

  • OAK–MDW, 11/12/2026: From $274
    12

    Thu

  • OAK–MDW, 11/13/2026: From $274
    13

    Fri

  • OAK–MDW, 11/14/2026: From $274
    14

    Sat

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

    Sun

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

    Mon

  • OAK–MDW, 11/17/2026: From $274
    17

    Tue

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

    Wed

  • OAK–MDW, 11/19/2026: From $284
    19

    Thu

  • OAK–MDW, 11/20/2026: From $284
    20

    Fri

  • OAK–MDW, 11/21/2026: From $284
    21

    Sat

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

    Sun

  • OAK–MDW, 11/23/2026: From $274
    23

    Mon

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

    Tue

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

    Wed

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

    Thu

  • OAK–MDW, 11/27/2026: From $274
    27

    Fri

  • OAK–MDW, 11/28/2026: From $364
    28

    Sat

  • OAK–MDW, 11/29/2026: From $399
    29

    Sun

  • OAK–MDW, 11/30/2026: From $198
    30

    Mon

  • OAK–MDW, 12/01/2026: From $160
    01

    Tue

    DEC

  • OAK–MDW, 12/02/2026: From $160
    02

    Wed

  • OAK–MDW, 12/03/2026: From $175
    03

    Thu

  • OAK–MDW: cmp-view-offers-disclaimer. Find Offers
    04

    Fri

  • OAK–MDW, 12/05/2026: From $160
    05

    Sat

  • OAK–MDW, 12/06/2026: From $234
    06

    Sun

  • OAK–MDW, 12/07/2026: From $175
    07

    Mon

  • OAK–MDW: cmp-view-offers-disclaimer. Find Offers
    08

    Tue

  • OAK–MDW, 12/09/2026: From $160
    09

    Wed

    • Range$160-$399

    *Fares displayed have been collected within the last 24 hours and may no longer be available at time of booking. Additional fees and charges for optional products and services may apply. Modifying this information may result in a different fare. To find the most updated fare, please visit Southwest.com. Fares listed are Basic, which are subject to additional terms and conditions.

    Flight Details

    Departing from:
    Oakland International Airport
    Arriving at:
    Chicago Midway International Airport
    Average flight time:
    4 hours 5 minutes
    Distance:
    1844 miles

    Questions we hear the most

    The average flight time from Oakland to Chicago (Midway) is 4 hours 5 minutes.
    There are 156 weekly flights from Oakland to Chicago (Midway) on Southwest Airlines.
    Yes, Southwest flies nonstop from Oakland to Chicago (Midway) once per day from Monday through Friday.
    Yes, Southwest flies nonstop from Oakland to Chicago (Midway) once per day on Saturdays and 2 times per day on Sundays.
    To find the lowest fares by day and time to fly Oakland to Chicago (Midway) with Southwest, check out our Low Fare Calendar.
    You can rent a car at Chicago Midway International Airport book yours with your flight.
    Yes! Flights from Oakland to Chicago (Midway)—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.

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