Southwest® flights from Chicago-Midway to Oakland from $165

Promo Code

Low fares from Chicago-Midway to Oakland

$

Chicago-Midway (MDW)to

Oakland (OAK)
Depart: 12/08/2026

One-way

Basic

From
$165
Seen: 18 hrs ago

Chicago-Midway (MDW)to

Oakland (OAK)
Depart: 01/05/2027

One-way

Basic

From
$165
Seen: 16 hrs ago

Chicago-Midway (MDW)to

Oakland (OAK)
Depart: 12/16/2026

One-way

Basic

From
$165
Seen: 19 hrs ago

Chicago-Midway (MDW)to

Oakland (OAK)
Depart: 02/06/2027

One-way

Basic

From
$165
Seen: 16 hrs ago

Chicago-Midway (MDW)to

Oakland (OAK)
Depart: 01/23/2027

One-way

Basic

From
$165
Seen: 13 hrs ago

Chicago-Midway (MDW)to

Oakland (OAK)
Depart: 12/09/2026

One-way

Basic

From
$165
Seen: 10 hrs ago

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Explore flights from Chicago-Midway to Oakland

Nov 2026
From$222*
Seen: 7 hrs ago
One Way/Basic
Dec 2026
From$165*
Seen: 18 hrs ago
One Way/Basic
Jan 2027
From$165*
Seen: 14 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $165
cmp-daily-histogram-bars-legend-max-price-aria-label $477
Displaying fares for November-2026
  • MDW–OAK, 11/11/2026: From $274
    11

    Wed

    NOV

  • MDW–OAK, 11/12/2026: From $274
    12

    Thu

  • MDW–OAK, 11/13/2026: From $274
    13

    Fri

  • MDW–OAK, 11/14/2026: From $274
    14

    Sat

  • MDW–OAK, 11/15/2026: From $274
    15

    Sun

  • MDW–OAK, 11/16/2026: From $274
    16

    Mon

  • MDW–OAK, 11/17/2026: From $274
    17

    Tue

  • MDW–OAK, 11/18/2026: From $222
    18

    Wed

  • MDW–OAK, 11/19/2026: From $279
    19

    Thu

  • MDW–OAK, 11/20/2026: From $274
    20

    Fri

  • MDW–OAK, 11/21/2026: From $274
    21

    Sat

  • MDW–OAK, 11/22/2026: From $274
    22

    Sun

  • MDW–OAK, 11/23/2026: From $274
    23

    Mon

  • MDW–OAK, 11/24/2026: From $274
    24

    Tue

  • MDW–OAK, 11/25/2026: From $274
    25

    Wed

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

    Thu

  • MDW–OAK, 11/27/2026: From $342
    27

    Fri

  • MDW–OAK, 11/28/2026: From $477
    28

    Sat

  • MDW–OAK, 11/29/2026: From $443
    29

    Sun

  • MDW–OAK, 11/30/2026: From $352
    30

    Mon

  • MDW–OAK, 12/01/2026: From $241
    01

    Tue

    DEC

  • MDW–OAK, 12/02/2026: From $175
    02

    Wed

  • MDW–OAK, 12/03/2026: From $185
    03

    Thu

  • MDW–OAK, 12/04/2026: From $200
    04

    Fri

  • MDW–OAK, 12/05/2026: From $165
    05

    Sat

  • MDW–OAK, 12/06/2026: From $234
    06

    Sun

  • MDW–OAK, 12/07/2026: From $185
    07

    Mon

  • MDW–OAK, 12/08/2026: From $165
    08

    Tue

  • MDW–OAK, 12/09/2026: From $165
    09

    Wed

  • MDW–OAK, 12/10/2026: From $185
    10

    Thu

    • Range$165-$477

    *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

    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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