Southwest® flights from Indianapolis to Chicago (O'Hare)

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Low fares from Indianapolis to Chicago (O'Hare)

$

Indianapolis (IND)to

Chicago (Midway) (MDW)
Depart: 11/07/2026

One-way

Basic

From
$79
Seen: 22 hrs ago

Indianapolis (IND)to

Chicago (Midway) (MDW)
Depart: 09/26/2026

One-way

Basic

From
$79
Seen: 20 hrs ago

Indianapolis (IND)to

Chicago (Midway) (MDW)
Depart: 10/13/2026

One-way

Basic

From
$79
Seen: 3 hrs ago

Indianapolis (IND)to

Chicago (Midway) (MDW)
Depart: 10/07/2026

One-way

Basic

From
$79
Seen: 3 hrs ago

Indianapolis (IND)to

Chicago (Midway) (MDW)
Depart: 10/14/2026

One-way

Basic

From
$79
Seen: 4 hrs ago

Indianapolis (IND)to

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

One-way

Basic

From
$79
Seen: 8 hrs ago

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Explore flights from Indianapolis to Chicago (O'Hare)

Aug 2026
From$246*
Seen: 22 hrs ago
One Way/Basic
Sep 2026
From$79*
Seen: 13 hrs ago
One Way/Basic
Oct 2026
From$79*
Seen: 20 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $79
cmp-daily-histogram-bars-legend-max-price-aria-label $299
Displaying fares for August-2026
  • IND–MDW, 08/25/2026: From $246
    25

    Tue

    AUG

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

    Wed

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

    Thu

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

    Fri

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

    Sat

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

    Sun

  • IND–MDW: cmp-view-offers-disclaimer. Find Offers
    31

    Mon

  • IND–MDW, 09/01/2026: From $246
    01

    Tue

    SEP

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

    Wed

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

    Thu

  • IND–MDW: cmp-view-offers-disclaimer. Find Offers
    04

    Fri

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

    Sat

  • IND–MDW, 09/06/2026: From $160
    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: cmp-view-offers-disclaimer. Find Offers
    12

    Sat

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

    Sun

  • IND–MDW: cmp-view-offers-disclaimer. Find Offers
    14

    Mon

  • IND–MDW, 09/15/2026: From $79
    15

    Tue

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

    Wed

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

    Thu

  • IND–MDW, 09/18/2026: From $119
    18

    Fri

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

    Sat

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

    Sun

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

    Mon

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

    Tue

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

    Wed

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

    Thu

    • Range$79-$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:
    O'Hare International Airport
    Distance:
    177 miles

    Route Information

    13† 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 13 weekly flights from Indianapolis to Chicago (O'Hare) on Southwest Airlines.
    To find the lowest fares by day and time to fly Indianapolis to Chicago (O'Hare) with Southwest, check out our Low Fare Calendar.
    You can rent a car at O'Hare International Airport book yours with your flight.
    Yes! Flights from Indianapolis to Chicago (O'Hare)—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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