Southwest® flights from Chicago-Midway to Oakland from $168

Promo Code

Low fares from Chicago-Midway to Oakland

$

Chicago-Midway (MDW)to

Oakland (OAK)
Depart: 11/17/2026

One-way

Basic

From
$168
Seen: 22 hrs ago

Chicago-Midway (MDW)to

Oakland (OAK)
Depart: 11/14/2026

One-way

Basic

From
$168
Seen: 17 hrs ago

Chicago-Midway (MDW)to

Oakland (OAK)
Depart: 10/22/2026

One-way

Basic

From
$168
Seen: 22 hrs ago

Chicago-Midway (MDW)to

Oakland (OAK)
Depart: 09/30/2026

One-way

Basic

From
$168
Seen: 22 hrs ago

Chicago-Midway (MDW)to

Oakland (OAK)
Depart: 10/31/2026

One-way

Basic

From
$168
Seen: 13 hrs ago

Chicago-Midway (MDW)to

Oakland (OAK)
Depart: 11/18/2026

One-way

Basic

From
$168
Seen: 6 hrs ago

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Explore flights from Chicago-Midway to Oakland

Sep 2026
From$168*
Seen: 22 hrs ago
One Way/Basic
Oct 2026
From$168*
Seen: 18 hrs ago
One Way/Basic
Nov 2026
From$168*
Seen: 5 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $168
cmp-daily-histogram-bars-legend-max-price-aria-label $311
Displaying fares for September-2026
  • MDW–OAK, 09/11/2026: From $291
    11

    Fri

    SEP

  • MDW–OAK, 09/12/2026: From $257
    12

    Sat

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

    Sun

  • MDW–OAK, 09/14/2026: From $291
    14

    Mon

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

    Tue

  • MDW–OAK, 09/16/2026: From $257
    16

    Wed

  • MDW–OAK, 09/17/2026: From $291
    17

    Thu

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

    Fri

  • MDW–OAK, 09/19/2026: From $262
    19

    Sat

  • MDW–OAK, 09/20/2026: From $301
    20

    Sun

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

    Mon

  • MDW–OAK, 09/22/2026: From $257
    22

    Tue

  • MDW–OAK, 09/23/2026: From $267
    23

    Wed

  • MDW–OAK, 09/24/2026: From $301
    24

    Thu

  • MDW–OAK, 09/25/2026: From $291
    25

    Fri

  • MDW–OAK: cmp-view-offers-disclaimer. Find Offers
    26

    Sat

  • MDW–OAK, 09/27/2026: From $311
    27

    Sun

  • MDW–OAK, 09/28/2026: From $291
    28

    Mon

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

    Tue

  • MDW–OAK, 09/30/2026: From $168
    30

    Wed

  • MDW–OAK, 10/01/2026: From $168
    01

    Thu

    OCT

  • MDW–OAK, 10/02/2026: From $182
    02

    Fri

  • MDW–OAK, 10/03/2026: From $178
    03

    Sat

  • MDW–OAK, 10/04/2026: From $249
    04

    Sun

  • MDW–OAK, 10/05/2026: From $168
    05

    Mon

  • MDW–OAK, 10/06/2026: From $168
    06

    Tue

  • MDW–OAK, 10/07/2026: From $168
    07

    Wed

  • MDW–OAK, 10/08/2026: From $168
    08

    Thu

  • MDW–OAK, 10/09/2026: From $182
    09

    Fri

  • MDW–OAK, 10/10/2026: From $168
    10

    Sat

    • Range$168-$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:
    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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