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

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Low fares from Chicago (Midway) to Oakland

$

Chicago (Midway) (MDW)to

Oakland (OAK)
Depart: 08/27/2026

One-way

Basic

From
$119
Seen: 15 hrs ago

Chicago (Midway) (MDW)to

Oakland (OAK)
Depart: 09/26/2026

One-way

Basic

From
$119
Seen: 20 hrs ago

Chicago (Midway) (MDW)to

Oakland (OAK)
Depart: 09/30/2026

One-way

Basic

From
$119
Seen: 7 hrs ago

Chicago (Midway) (MDW)to

Oakland (OAK)
Depart: 09/28/2026

One-way

Basic

From
$119
Seen: 8 hrs ago

Chicago (Midway) (MDW)to

Oakland (OAK)
Depart: 09/23/2026

One-way

Basic

From
$119
Seen: 8 hrs ago

Chicago (Midway) (MDW)to

Oakland (OAK)
Depart: 09/12/2026

One-way

Basic

From
$119
Seen: 4 hrs ago

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Explore flights from Chicago (Midway) to Oakland

Jul 2026
From$271*
Seen: 5 hrs ago
One Way/Basic
Aug 2026
From$119*
Seen: 15 hrs ago
One Way/Basic
Sep 2026
From$119*
Seen: 9 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $119
cmp-daily-histogram-bars-legend-max-price-aria-label $325
Displaying fares for July-2026
  • MDW–OAK, 07/31/2026: From $271
    31

    Fri

    JUL

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

    Sat

  • MDW–OAK, 08/02/2026: From $302
    02

    Sun

  • MDW–OAK, 08/03/2026: From $281
    03

    Mon

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

    Tue

  • MDW–OAK, 08/05/2026: From $237
    05

    Wed

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

    Thu

  • MDW–OAK, 08/07/2026: From $271
    07

    Fri

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

    Sat

  • MDW–OAK, 08/09/2026: From $325
    09

    Sun

  • MDW–OAK, 08/10/2026: From $281
    10

    Mon

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

    Tue

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

    Wed

  • MDW–OAK: cmp-view-offers-disclaimer. Find Offers
    13

    Thu

  • MDW–OAK, 08/14/2026: From $271
    14

    Fri

  • MDW–OAK, 08/15/2026: From $247
    15

    Sat

  • MDW–OAK, 08/16/2026: From $281
    16

    Sun

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

    Mon

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

    Tue

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

    Wed

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

    Thu

  • MDW–OAK: cmp-view-offers-disclaimer. Find Offers
    21

    Fri

  • MDW–OAK, 08/22/2026: From $183
    22

    Sat

  • MDW–OAK: cmp-view-offers-disclaimer. Find Offers
    23

    Sun

  • MDW–OAK, 08/24/2026: From $129
    24

    Mon

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

    Tue

  • MDW–OAK, 08/26/2026: From $119
    26

    Wed

  • MDW–OAK, 08/27/2026: From $119
    27

    Thu

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

    Fri

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

    Sat

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

    Sun

    • Range$119-$325

    *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:
    Chicago Midway International Airport
    Arriving at:
    Oakland International Airport
    Average flight time:
    4 hours 32 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 Chicago (Midway) to Oakland is 4 hours 32 minutes.
    There are 156 weekly flights from Chicago (Midway) to Oakland on Southwest Airlines.
    Yes, Southwest flies nonstop from Chicago (Midway) to Oakland once per day from Monday through Friday.
    Yes, Southwest flies nonstop from Chicago (Midway) to Oakland once per day on Saturdays and 2 times per day on Sundays.
    To find the lowest fares by day and time to fly Chicago (Midway) to Oakland with Southwest, check out our Low Fare Calendar.
    You can rent a car at Oakland International Airport book yours with your flight.
    Yes! Flights from Chicago (Midway) to Oakland—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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