Southwest® flights from Orange County/Santa Ana to Chicago (Midway) from $150

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Low fares from Orange County/Santa Ana to Chicago (Midway)

$

Orange County/Santa Ana (SNA)to

Chicago (Midway) (MDW)
Depart: 11/05/2026

One-way

Basic

From
$150
Seen: 45 minutes ago

Orange County/Santa Ana (SNA)to

Chicago (Midway) (MDW)
Depart: 11/11/2026

One-way

Basic

From
$155
Seen: 21 hrs ago

Orange County/Santa Ana (SNA)to

Chicago (Midway) (MDW)
Depart: 11/10/2026

One-way

Basic

From
$155
Seen: 4 hrs ago

Orange County/Santa Ana (SNA)to

Chicago (Midway) (MDW)
Depart: 10/15/2026

One-way

Basic

From
$155
Seen: 2 hrs ago

Orange County/Santa Ana (SNA)to

Chicago (Midway) (MDW)
Depart: 09/28/2026

One-way

Basic

From
$155
Seen: 5 hrs ago

Orange County/Santa Ana (SNA)to

Chicago (Midway) (MDW)
Depart: 09/14/2026

One-way

Basic

From
$155
Seen: 9 hrs ago

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Explore flights from Orange County/Santa Ana to Chicago (Midway)

Aug 2026
From$253*
Seen: 10 hrs ago
One Way/Basic
Sep 2026
From$155*
Seen: 5 hrs ago
One Way/Basic
Oct 2026
From$155*
Seen: 18 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $155
cmp-daily-histogram-bars-legend-max-price-aria-label $319
Displaying fares for August-2026
  • SNA–MDW, 08/22/2026: From $253
    22

    Sat

    AUG

  • SNA–MDW, 08/23/2026: From $299
    23

    Sun

  • SNA–MDW, 08/24/2026: From $299
    24

    Mon

  • SNA–MDW, 08/25/2026: From $253
    25

    Tue

  • SNA–MDW, 08/26/2026: From $253
    26

    Wed

  • SNA–MDW, 08/27/2026: From $299
    27

    Thu

  • SNA–MDW, 08/28/2026: From $299
    28

    Fri

  • SNA–MDW, 08/29/2026: From $253
    29

    Sat

  • SNA–MDW, 08/30/2026: From $275
    30

    Sun

  • SNA–MDW, 08/31/2026: From $275
    31

    Mon

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

    Tue

    SEP

  • SNA–MDW, 09/02/2026: From $253
    02

    Wed

  • SNA–MDW, 09/03/2026: From $319
    03

    Thu

  • SNA–MDW, 09/04/2026: From $275
    04

    Fri

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

    Sat

  • SNA–MDW: cmp-view-offers-disclaimer. Find Offers
    06

    Sun

  • SNA–MDW: cmp-view-offers-disclaimer. Find Offers
    07

    Mon

  • SNA–MDW: cmp-view-offers-disclaimer. Find Offers
    08

    Tue

  • SNA–MDW, 09/09/2026: From $191
    09

    Wed

  • SNA–MDW, 09/10/2026: From $191
    10

    Thu

  • SNA–MDW, 09/11/2026: From $191
    11

    Fri

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

    Sat

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

    Sun

  • SNA–MDW, 09/14/2026: From $155
    14

    Mon

  • SNA–MDW, 09/15/2026: From $155
    15

    Tue

  • SNA–MDW, 09/16/2026: From $155
    16

    Wed

  • SNA–MDW: cmp-view-offers-disclaimer. Find Offers
    17

    Thu

  • SNA–MDW, 09/18/2026: From $179
    18

    Fri

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

    Sat

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

    Sun

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

    Mon

    • Range$155-$319

    *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:
    John Wayne Airport
    Arriving at:
    Chicago Midway International Airport
    Distance:
    1731 miles

    Route Information

    154† 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 154 weekly flights from Orange County/Santa Ana to Chicago (Midway) on Southwest Airlines.
    To find the lowest fares by day and time to fly Orange County/Santa Ana 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 Orange County/Santa Ana 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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