Southwest® flights from Indianapolis to Chicago (Midway) from $79

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Low fares from Indianapolis to Chicago (Midway)

$

Indianapolis (IND)to

Chicago (Midway) (MDW)
Depart: 11/23/2026

One-way

Basic

From
$79
Seen: 16 hrs ago

Indianapolis (IND)to

Chicago (Midway) (MDW)
Depart: 10/03/2026

One-way

Basic

From
$79
Seen: 15 hrs ago

Indianapolis (IND)to

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

One-way

Basic

From
$79
Seen: 2 hrs ago

Indianapolis (IND)to

Chicago (Midway) (MDW)
Depart: 11/12/2026

One-way

Basic

From
$79
Seen: 2 hrs ago

Indianapolis (IND)to

Chicago (Midway) (MDW)
Depart: 10/22/2026

One-way

Basic

From
$79
Seen: 12 hrs ago

Indianapolis (IND)to

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

One-way

Basic

From
$79
Seen: 11 hrs ago

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Explore flights from Indianapolis to Chicago (Midway)

Aug 2026
From$246*
Seen: 20 hrs ago
One Way/Basic
Sep 2026
From$89*
Seen: 12 hrs ago
One Way/Basic
Oct 2026
From$79*
Seen: 11 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $119
cmp-daily-histogram-bars-legend-max-price-aria-label $299
Displaying fares for August-2026
  • IND–MDW, 08/23/2026: From $299
    23

    Sun

    AUG

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

    Mon

  • IND–MDW: cmp-view-offers-disclaimer. Find Offers
    25

    Tue

  • IND–MDW, 08/26/2026: From $246
    26

    Wed

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    27

    Thu

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

    Fri

  • IND–MDW, 08/29/2026: From $246
    29

    Sat

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    30

    Sun

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    31

    Mon

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

    Tue

    SEP

  • IND–MDW, 09/02/2026: From $246
    02

    Wed

  • IND–MDW, 09/03/2026: From $299
    03

    Thu

  • IND–MDW, 09/04/2026: From $299
    04

    Fri

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    05

    Sat

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    06

    Sun

  • IND–MDW, 09/07/2026: From $225
    07

    Mon

  • IND–MDW, 09/08/2026: From $225
    08

    Tue

  • IND–MDW, 09/09/2026: From $160
    09

    Wed

  • IND–MDW, 09/10/2026: From $160
    10

    Thu

  • IND–MDW, 09/11/2026: From $160
    11

    Fri

  • IND–MDW, 09/12/2026: From $160
    12

    Sat

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    13

    Sun

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    14

    Mon

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    15

    Tue

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

    Wed

  • IND–MDW, 09/17/2026: From $119
    17

    Thu

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

    Fri

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

    Sat

  • IND–MDW, 09/20/2026: From $174
    20

    Sun

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    21

    Mon

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

    Tue

    • Range$119-$299

    *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:
    Indianapolis International Airport
    Arriving at:
    Chicago Midway International Airport
    Average flight time:
    1 hour 6 minutes
    Distance:
    162 miles

    Route Information

    99† Weekly flights
    • 2‡ Nonstop flights per day Monday through Friday
    • 2‡ Nonstop flights 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 Indianapolis to Chicago (Midway) is 1 hour 6 minutes.
    There are 99 weekly flights from Indianapolis to Chicago (Midway) on Southwest Airlines.
    Yes, Southwest flies nonstop from Indianapolis to Chicago (Midway) 2 times per day from Monday through Friday.
    Yes, Southwest flies nonstop from Indianapolis to Chicago (Midway) 2 times per day on Saturdays and Sundays.
    To find the lowest fares by day and time to fly Indianapolis 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 Indianapolis 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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