Southwest® flights from Santa Barbara to Chicago (Midway) from $180

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Low fares from Santa Barbara to Chicago (Midway)

$

Santa Barbara (SBA)to

Chicago (Midway) (MDW)
Depart: 08/25/2026

One-way

Basic

From
$180
Seen: 5 hrs ago

Santa Barbara (SBA)to

Chicago (Midway) (MDW)
Depart: 10/16/2026

One-way

Basic

From
$180
Seen: 10 hrs ago

Santa Barbara (SBA)to

Chicago (Midway) (MDW)
Depart: 09/21/2026

One-way

Basic

From
$180
Seen: 1 hour ago

Santa Barbara (SBA)to

Chicago (Midway) (MDW)
Depart: 09/04/2026

One-way

Basic

From
$180
Seen: 2 hrs ago

Santa Barbara (SBA)to

Chicago (Midway) (MDW)
Depart: 08/31/2026

One-way

Basic

From
$180
Seen: 12 hrs ago

Santa Barbara (SBA)to

Chicago (Midway) (MDW)
Depart: 09/25/2026

One-way

Basic

From
$180
Seen: 15 hrs ago

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Explore flights from Santa Barbara to Chicago (Midway)

Aug 2026
From$180*
Seen: 5 hrs ago
One Way/Basic
Sep 2026
From$180*
Seen: 15 hrs ago
One Way/Basic
Oct 2026
From$180*
Seen: 5 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $180
cmp-daily-histogram-bars-legend-max-price-aria-label $345
Displaying fares for August-2026
  • SBA–MDW, 08/01/2026: From $345
    01

    Sat

    AUG

  • SBA–MDW, 08/02/2026: From $340
    02

    Sun

  • SBA–MDW, 08/03/2026: From $340
    03

    Mon

  • SBA–MDW, 08/04/2026: From $340
    04

    Tue

  • SBA–MDW, 08/05/2026: From $340
    05

    Wed

  • SBA–MDW, 08/06/2026: From $340
    06

    Thu

  • SBA–MDW, 08/07/2026: From $275
    07

    Fri

  • SBA–MDW, 08/08/2026: From $280
    08

    Sat

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

    Sun

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

    Mon

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

    Tue

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

    Wed

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

    Thu

  • SBA–MDW, 08/14/2026: From $215
    14

    Fri

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

    Sat

  • SBA–MDW: cmp-view-offers-disclaimer. Find Offers
    16

    Sun

  • SBA–MDW, 08/17/2026: From $215
    17

    Mon

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

    Tue

  • SBA–MDW: cmp-view-offers-disclaimer. Find Offers
    19

    Wed

  • SBA–MDW: cmp-view-offers-disclaimer. Find Offers
    20

    Thu

  • SBA–MDW, 08/21/2026: From $180
    21

    Fri

  • SBA–MDW: cmp-view-offers-disclaimer. Find Offers
    22

    Sat

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

    Sun

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

    Mon

  • SBA–MDW, 08/25/2026: From $180
    25

    Tue

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

    Wed

  • SBA–MDW: cmp-view-offers-disclaimer. Find Offers
    27

    Thu

  • SBA–MDW: cmp-view-offers-disclaimer. Find Offers
    28

    Fri

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

    Sat

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

    Sun

  • SBA–MDW, 08/31/2026: From $180
    31

    Mon

    • Range$180-$345

    *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:
    Santa Barbara Municipal Airport
    Arriving at:
    Chicago Midway International Airport
    Distance:
    1809 miles

    Route Information

    68† 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 68 weekly flights from Santa Barbara to Chicago (Midway) on Southwest Airlines.
    To find the lowest fares by day and time to fly Santa Barbara 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 Santa Barbara 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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