Southwest® flights from Indianapolis to Chicago-Midway from $145

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Low fares from Indianapolis to Chicago-Midway

$

Indianapolis (IND)to

Chicago-Midway (MDW)
Depart: 01/05/2027

One-way

Basic

From
$145
Seen: 16 hrs ago

Indianapolis (IND)to

Chicago-Midway (MDW)
Depart: 12/09/2026

One-way

Basic

From
$145
Seen: 17 hrs ago

Indianapolis (IND)to

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

One-way

Basic

From
$145
Seen: 6 hrs ago

Indianapolis (IND)to

Chicago-Midway (MDW)
Depart: 12/08/2026

One-way

Basic

From
$145
Seen: 19 hrs ago

Indianapolis (IND)to

Chicago-Midway (MDW)
Depart: 12/10/2026

One-way

Basic

From
$165
Seen: 17 hrs ago

Indianapolis (IND)to

Chicago-Midway (MDW)
Depart: 12/03/2026

One-way

Basic

From
$165
Seen: 1 hour ago

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Explore flights from Indianapolis to Chicago-Midway

Nov 2026
From$260*
Seen: 10 hrs ago
One Way/Basic
Dec 2026
From$145*
Seen: 19 hrs ago
One Way/Basic
Jan 2027
From$145*
Seen: 16 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $145
cmp-daily-histogram-bars-legend-max-price-aria-label $334
Displaying fares for November-2026
  • IND–MDW, 11/13/2026: From $262
    13

    Fri

    NOV

  • IND–MDW, 11/14/2026: From $262
    14

    Sat

  • IND–MDW, 11/15/2026: From $334
    15

    Sun

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

    Mon

  • IND–MDW, 11/17/2026: From $262
    17

    Tue

  • IND–MDW, 11/18/2026: From $267
    18

    Wed

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

    Thu

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

    Fri

  • IND–MDW, 11/21/2026: From $267
    21

    Sat

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

    Sun

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

    Mon

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

    Tue

  • IND–MDW, 11/25/2026: From $260
    25

    Wed

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

    Thu

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

    Fri

  • IND–MDW, 11/28/2026: From $262
    28

    Sat

  • IND–MDW, 11/29/2026: From $262
    29

    Sun

  • IND–MDW, 11/30/2026: From $262
    30

    Mon

  • IND–MDW, 12/01/2026: From $260
    01

    Tue

    DEC

  • IND–MDW: cmp-view-offers-disclaimer. Find Offers
    02

    Wed

  • IND–MDW, 12/03/2026: From $165
    03

    Thu

  • IND–MDW, 12/04/2026: From $180
    04

    Fri

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    05

    Sat

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

    Sun

  • IND–MDW, 12/07/2026: From $165
    07

    Mon

  • IND–MDW, 12/08/2026: From $145
    08

    Tue

  • IND–MDW, 12/09/2026: From $145
    09

    Wed

  • IND–MDW, 12/10/2026: From $165
    10

    Thu

  • IND–MDW, 12/11/2026: From $180
    11

    Fri

  • IND–MDW, 12/12/2026: From $145
    12

    Sat

    • Range$145-$334

    *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

    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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