Southwest® flights from Oakland to Chicago (O'Hare)

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Low fares from Oakland to Chicago (O'Hare)

$

Oakland (OAK)to

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

One-way

Basic

From
$119
Seen: 6 hrs ago

Oakland (OAK)to

Chicago (Midway) (MDW)
Depart: 09/06/2026

One-way

Basic

From
$119
Seen: 31 minutes ago

Oakland (OAK)to

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

One-way

Basic

From
$129
Seen: 4 hrs ago

Oakland (OAK)to

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

One-way

Basic

From
$129
Seen: 22 hrs ago

Oakland (OAK)to

Chicago (Midway) (MDW)
Depart: 10/22/2026

One-way

Basic

From
$129
Seen: 18 hrs ago

Oakland (OAK)to

Chicago (Midway) (MDW)
Depart: 10/17/2026

One-way

Basic

From
$129
Seen: 16 hrs ago

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Explore flights from Oakland to Chicago (O'Hare)

Aug 2026
From$129*
Seen: 23 hrs ago
One Way/Basic
Sep 2026
From$119*
Seen: 6 hrs ago
One Way/Basic
Oct 2026
From$129*
Seen: 6 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $129
cmp-daily-histogram-bars-legend-max-price-aria-label $287
Displaying fares for August-2026
  • OAK–MDW, 08/05/2026: From $237
    05

    Wed

    AUG

  • OAK–MDW, 08/06/2026: From $281
    06

    Thu

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

    Fri

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

    Sat

  • OAK–MDW, 08/09/2026: From $271
    09

    Sun

  • OAK–MDW: cmp-view-offers-disclaimer. Find Offers
    10

    Mon

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

    Tue

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

    Wed

  • OAK–MDW, 08/13/2026: From $271
    13

    Thu

  • OAK–MDW, 08/14/2026: From $281
    14

    Fri

  • OAK–MDW: cmp-view-offers-disclaimer. Find Offers
    15

    Sat

  • OAK–MDW, 08/16/2026: From $271
    16

    Sun

  • OAK–MDW, 08/17/2026: From $271
    17

    Mon

  • OAK–MDW, 08/18/2026: From $287
    18

    Tue

  • OAK–MDW, 08/19/2026: From $237
    19

    Wed

  • OAK–MDW, 08/20/2026: From $281
    20

    Thu

  • OAK–MDW, 08/21/2026: From $271
    21

    Fri

  • OAK–MDW, 08/22/2026: From $247
    22

    Sat

  • OAK–MDW, 08/23/2026: From $271
    23

    Sun

  • OAK–MDW: cmp-view-offers-disclaimer. Find Offers
    24

    Mon

  • OAK–MDW, 08/25/2026: From $129
    25

    Tue

  • OAK–MDW, 08/26/2026: From $139
    26

    Wed

  • OAK–MDW, 08/27/2026: From $139
    27

    Thu

  • OAK–MDW, 08/28/2026: From $179
    28

    Fri

  • OAK–MDW, 08/29/2026: From $129
    29

    Sat

  • OAK–MDW: cmp-view-offers-disclaimer. Find Offers
    30

    Sun

  • OAK–MDW: cmp-view-offers-disclaimer. Find Offers
    31

    Mon

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

    Tue

    SEP

  • OAK–MDW, 09/02/2026: From $139
    02

    Wed

  • OAK–MDW, 09/03/2026: From $192
    03

    Thu

  • OAK–MDW, 09/04/2026: From $229
    04

    Fri

    • Range$129-$287

    *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:
    O'Hare International Airport
    Distance:
    1836 miles

    Route Information

    96† Weekly flights

    † 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

    There are 96 weekly flights from Oakland to Chicago (O'Hare) on Southwest Airlines.
    To find the lowest fares by day and time to fly Oakland to Chicago (O'Hare) with Southwest, check out our Low Fare Calendar.
    You can rent a car at O'Hare International Airport book yours with your flight.
    Yes! Flights from Oakland to Chicago (O'Hare)—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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