Southwest® flights from Oakland to Chicago (Midway) from $119

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Low fares from Oakland to Chicago (Midway)

$

Oakland (OAK)to

Chicago (Midway) (MDW)
Depart: 09/19/2026

One-way

Basic

From
$119
Seen: 16 hrs ago

Oakland (OAK)to

Chicago (Midway) (MDW)
Depart: 09/15/2026

One-way

Basic

From
$119
Seen: 17 hrs ago

Oakland (OAK)to

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

One-way

Basic

From
$119
Seen: 14 hrs ago

Oakland (OAK)to

Chicago (Midway) (MDW)
Depart: 10/29/2026

One-way

Basic

From
$119
Seen: 9 hrs ago

Oakland (OAK)to

Chicago (Midway) (MDW)
Depart: 09/22/2026

One-way

Basic

From
$119
Seen: 4 hrs ago

Oakland (OAK)to

Chicago (Midway) (MDW)
Depart: 10/05/2026

One-way

Basic

From
$119
Seen: 23 hrs ago

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Explore flights from Oakland to Chicago (Midway)

Aug 2026
From$227*
Seen: 12 hrs ago
One Way/Basic
Sep 2026
From$119*
Seen: 11 hrs ago
One Way/Basic
Oct 2026
From$119*
Seen: 7 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $119
cmp-daily-histogram-bars-legend-max-price-aria-label $271
Displaying fares for August-2026
  • OAK–MDW, 08/21/2026: From $261
    21

    Fri

    AUG

  • OAK–MDW, 08/22/2026: From $227
    22

    Sat

  • OAK–MDW, 08/23/2026: From $261
    23

    Sun

  • OAK–MDW, 08/24/2026: From $261
    24

    Mon

  • OAK–MDW, 08/25/2026: From $227
    25

    Tue

  • OAK–MDW, 08/26/2026: From $227
    26

    Wed

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

    Thu

  • OAK–MDW, 08/28/2026: From $261
    28

    Fri

  • OAK–MDW, 08/29/2026: From $227
    29

    Sat

  • OAK–MDW, 08/30/2026: From $261
    30

    Sun

  • OAK–MDW, 08/31/2026: From $261
    31

    Mon

  • OAK–MDW, 09/01/2026: From $227
    01

    Tue

    SEP

  • OAK–MDW, 09/02/2026: From $237
    02

    Wed

  • OAK–MDW, 09/03/2026: From $271
    03

    Thu

  • OAK–MDW, 09/04/2026: From $271
    04

    Fri

  • OAK–MDW, 09/05/2026: From $208
    05

    Sat

  • OAK–MDW: cmp-view-offers-disclaimer. Find Offers
    06

    Sun

  • OAK–MDW, 09/07/2026: From $261
    07

    Mon

  • OAK–MDW, 09/08/2026: From $227
    08

    Tue

  • OAK–MDW, 09/09/2026: From $208
    09

    Wed

  • OAK–MDW, 09/10/2026: From $129
    10

    Thu

  • OAK–MDW, 09/11/2026: From $129
    11

    Fri

  • OAK–MDW: cmp-view-offers-disclaimer. Find Offers
    12

    Sat

  • OAK–MDW, 09/13/2026: From $209
    13

    Sun

  • OAK–MDW, 09/14/2026: From $119
    14

    Mon

  • OAK–MDW, 09/15/2026: From $119
    15

    Tue

  • OAK–MDW, 09/16/2026: From $129
    16

    Wed

  • OAK–MDW, 09/17/2026: From $170
    17

    Thu

  • OAK–MDW, 09/18/2026: From $129
    18

    Fri

  • OAK–MDW, 09/19/2026: From $119
    19

    Sat

  • OAK–MDW: cmp-view-offers-disclaimer. Find Offers
    20

    Sun

    • Range$119-$271

    *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

    Route Information

    156† Weekly flights
    • 1‡ Nonstop flight per day Monday through Friday
    • 1‡ Nonstop flight on Saturday
    • 2‡ Nonstop flights on Sunday

    † Weekly flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025. Note: route may not operate every day of the week.

    ‡ Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025.

    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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