Southwest® flights from Indianapolis to Chicago-Midway from $163

Promo Code

Low fares from Indianapolis to Chicago-Midway

$

Indianapolis (IND)to

Chicago-Midway (MDW)
Depart: 12/02/2026

One-way

Basic

From
$163
Seen: 20 hrs ago

Indianapolis (IND)to

Chicago-Midway (MDW)
Depart: 10/21/2026

One-way

Basic

From
$163
Seen: 12 hrs ago

Indianapolis (IND)to

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

One-way

Basic

From
$163
Seen: 17 hrs ago

Indianapolis (IND)to

Chicago-Midway (MDW)
Depart: 11/13/2026

One-way

Basic

From
$163
Seen: 17 hrs ago

Indianapolis (IND)to

Chicago-Midway (MDW)
Depart: 10/05/2026

One-way

Basic

From
$163
Seen: 23 hrs ago

Indianapolis (IND)to

Chicago-Midway (MDW)
Depart: 10/06/2026

One-way

Basic

From
$163
Seen: 20 hrs ago

Looking for more low-fare flights?

Check out the Low Fare Calendar to find a fare that works for you. Just choose the month you want to depart and return, and we’ll show you the best fares available.

Find low fares

Explore flights from Indianapolis to Chicago-Midway

Sep 2026
From$245*
Seen: 3 hrs ago
One Way/Basic
Oct 2026
From$163*
Seen: 23 hrs ago
One Way/Basic
Nov 2026
From$163*
Seen: 19 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $163
cmp-daily-histogram-bars-legend-max-price-aria-label $276
Displaying fares for September-2026
  • IND–MDW, 09/12/2026: From $245
    12

    Sat

    SEP

  • IND–MDW, 09/13/2026: From $276
    13

    Sun

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

    Mon

  • IND–MDW, 09/15/2026: From $245
    15

    Tue

  • IND–MDW, 09/16/2026: From $255
    16

    Wed

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

    Thu

  • IND–MDW, 09/18/2026: From $276
    18

    Fri

  • IND–MDW, 09/19/2026: From $245
    19

    Sat

  • IND–MDW, 09/20/2026: From $276
    20

    Sun

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

    Mon

  • IND–MDW, 09/22/2026: From $245
    22

    Tue

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

    Wed

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

    Thu

  • IND–MDW, 09/25/2026: From $245
    25

    Fri

  • IND–MDW, 09/26/2026: From $245
    26

    Sat

  • IND–MDW, 09/27/2026: From $245
    27

    Sun

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

    Mon

  • IND–MDW, 09/29/2026: From $245
    29

    Tue

  • IND–MDW, 09/30/2026: From $245
    30

    Wed

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

    Thu

    OCT

  • IND–MDW, 10/02/2026: From $163
    02

    Fri

  • IND–MDW, 10/03/2026: From $184
    03

    Sat

  • IND–MDW, 10/04/2026: From $184
    04

    Sun

  • IND–MDW, 10/05/2026: From $163
    05

    Mon

  • IND–MDW, 10/06/2026: From $163
    06

    Tue

  • IND–MDW, 10/07/2026: From $184
    07

    Wed

  • IND–MDW, 10/08/2026: From $163
    08

    Thu

  • IND–MDW, 10/09/2026: From $204
    09

    Fri

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

    Sat

  • IND–MDW, 10/11/2026: From $184
    11

    Sun

    • Range$163-$276

    *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.

    Explore Flights from Other Popular Origins

    Popular Flights from Indianapolis