Southwest® flights from Oakland to Chicago-Midway from $122

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Low fares from Oakland to Chicago-Midway

$

Oakland (OAK)to

Chicago-Midway (MDW)
Depart: 11/26/2026

One-way

Basic

From
$122
Seen: 23 hrs ago

Oakland (OAK)to

Chicago-Midway (MDW)
Depart: 11/16/2026

One-way

Basic

From
$122
Seen: 21 hrs ago

Oakland (OAK)to

Chicago-Midway (MDW)
Depart: 12/08/2026

One-way

Basic

From
$122
Seen: 5 hrs ago

Oakland (OAK)to

Chicago-Midway (MDW)
Depart: 11/09/2026

One-way

Basic

From
$122
Seen: 7 hrs ago

Oakland (OAK)to

Chicago-Midway (MDW)
Depart: 11/17/2026

One-way

Basic

From
$122
Seen: 18 hrs ago

Oakland (OAK)to

Chicago-Midway (MDW)
Depart: 12/10/2026

One-way

Basic

From
$122
Seen: 12 hrs ago

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Explore flights from Oakland to Chicago-Midway

Oct 2026
From$271*
Seen: 2 hrs ago
One Way/Basic
Nov 2026
From$122*
Seen: 18 hrs ago
One Way/Basic
Dec 2026
From$122*
Seen: 12 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $122
cmp-daily-histogram-bars-legend-max-price-aria-label $311
Displaying fares for October-2026
  • OAK–MDW, 10/21/2026: From $271
    21

    Wed

    OCT

  • OAK–MDW, 10/22/2026: From $311
    22

    Thu

  • OAK–MDW, 10/23/2026: From $311
    23

    Fri

  • OAK–MDW, 10/24/2026: From $271
    24

    Sat

  • OAK–MDW, 10/25/2026: From $311
    25

    Sun

  • OAK–MDW, 10/26/2026: From $311
    26

    Mon

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

    Tue

  • OAK–MDW, 10/28/2026: From $271
    28

    Wed

  • OAK–MDW, 10/29/2026: From $311
    29

    Thu

  • OAK–MDW, 10/30/2026: From $311
    30

    Fri

  • OAK–MDW, 10/31/2026: From $271
    31

    Sat

  • OAK–MDW, 11/01/2026: From $311
    01

    Sun

    NOV

  • OAK–MDW, 11/02/2026: From $311
    02

    Mon

  • OAK–MDW, 11/03/2026: From $271
    03

    Tue

  • OAK–MDW, 11/04/2026: From $271
    04

    Wed

  • OAK–MDW, 11/05/2026: From $311
    05

    Thu

  • OAK–MDW, 11/06/2026: From $311
    06

    Fri

  • OAK–MDW, 11/07/2026: From $271
    07

    Sat

  • OAK–MDW, 11/08/2026: From $311
    08

    Sun

  • OAK–MDW, 11/09/2026: From $122
    09

    Mon

  • OAK–MDW, 11/10/2026: From $132
    10

    Tue

  • OAK–MDW, 11/11/2026: From $132
    11

    Wed

  • OAK–MDW, 11/12/2026: From $132
    12

    Thu

  • OAK–MDW, 11/13/2026: From $167
    13

    Fri

  • OAK–MDW: cmp-view-offers-disclaimer. Find Offers
    14

    Sat

  • OAK–MDW, 11/15/2026: From $247
    15

    Sun

  • OAK–MDW, 11/16/2026: From $122
    16

    Mon

  • OAK–MDW, 11/17/2026: From $122
    17

    Tue

  • OAK–MDW: cmp-view-offers-disclaimer. Find Offers
    18

    Wed

  • OAK–MDW, 11/19/2026: From $239
    19

    Thu

  • OAK–MDW, 11/20/2026: From $222
    20

    Fri

    • Range$122-$311

    *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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