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

Promo Code

Low fares from Oakland to Chicago (Midway)

$

Oakland (OAK)to

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

One-way

Basic

From
$119
Seen: 19 hrs ago

Oakland (OAK)to

Chicago (Midway) (MDW)
Depart: 09/12/2026

One-way

Basic

From
$119
Seen: 15 hrs ago

Oakland (OAK)to

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

One-way

Basic

From
$119
Seen: 12 hrs ago

Oakland (OAK)to

Chicago (Midway) (MDW)
Depart: 09/29/2026

One-way

Basic

From
$119
Seen: 23 hrs ago

Oakland (OAK)to

Chicago (Midway) (MDW)
Depart: 09/01/2026

One-way

Basic

From
$119
Seen: 5 hrs ago

Oakland (OAK)to

Chicago (Midway) (MDW)
Depart: 10/01/2026

One-way

Basic

From
$119
Seen: 22 hrs ago

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Explore flights from Oakland to Chicago (Midway)

Try alternate month or interact with individual days below in order to find offers.
Jul 2026
No result for this month.
Aug 2026
From$119*
Seen: 23 hrs ago
One Way/Basic
Sep 2026
From$119*
Seen: 15 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $119
cmp-daily-histogram-bars-legend-max-price-aria-label $281
Displaying fares for July-2026
  • OAK–MDW: cmp-view-offers-disclaimer. Find Offers
    31

    Fri

    JUL

  • OAK–MDW, 08/01/2026: From $247
    01

    Sat

  • OAK–MDW, 08/02/2026: From $271
    02

    Sun

  • OAK–MDW, 08/03/2026: From $271
    03

    Mon

  • OAK–MDW, 08/04/2026: From $247
    04

    Tue

  • OAK–MDW: cmp-view-offers-disclaimer. Find Offers
    05

    Wed

  • OAK–MDW, 08/06/2026: From $271
    06

    Thu

  • OAK–MDW, 08/07/2026: From $281
    07

    Fri

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

    Sat

  • OAK–MDW: cmp-view-offers-disclaimer. Find Offers
    09

    Sun

  • OAK–MDW, 08/10/2026: From $271
    10

    Mon

  • OAK–MDW, 08/11/2026: From $237
    11

    Tue

  • OAK–MDW, 08/12/2026: From $237
    12

    Wed

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

    Thu

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

    Fri

  • OAK–MDW, 08/15/2026: From $237
    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 $237
    18

    Tue

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

    Wed

  • OAK–MDW, 08/20/2026: From $129
    20

    Thu

  • OAK–MDW, 08/21/2026: From $179
    21

    Fri

  • OAK–MDW, 08/22/2026: From $129
    22

    Sat

  • OAK–MDW, 08/23/2026: From $209
    23

    Sun

  • OAK–MDW, 08/24/2026: From $119
    24

    Mon

  • OAK–MDW, 08/25/2026: From $119
    25

    Tue

  • OAK–MDW, 08/26/2026: From $129
    26

    Wed

  • OAK–MDW, 08/27/2026: From $129
    27

    Thu

  • OAK–MDW, 08/28/2026: From $182
    28

    Fri

  • OAK–MDW: cmp-view-offers-disclaimer. Find Offers
    29

    Sat

  • OAK–MDW, 08/30/2026: From $200
    30

    Sun

    • Range$119-$281

    *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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