Southwest® flights from Indianapolis to Chicago-Midway from $142

Promo Code

Low fares from Indianapolis to Chicago-Midway

$

Indianapolis (IND)to

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

One-way

Basic

From
$142
Seen: 18 hrs ago

Indianapolis (IND)to

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

One-way

Basic

From
$142
Seen: 22 hrs ago

Indianapolis (IND)to

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

One-way

Basic

From
$142
Seen: 6 hrs ago

Indianapolis (IND)to

Chicago-Midway (MDW)
Depart: 11/02/2026

One-way

Basic

From
$142
Seen: 19 hrs ago

Indianapolis (IND)to

Chicago-Midway (MDW)
Depart: 11/09/2026

One-way

Basic

From
$142
Seen: 21 hrs ago

Indianapolis (IND)to

Chicago-Midway (MDW)
Depart: 11/06/2026

One-way

Basic

From
$151
Seen: 22 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

Oct 2026
From$168*
Seen: 5 hrs ago
One Way/Basic
Nov 2026
From$142*
Seen: 22 hrs ago
One Way/Basic
Dec 2026
From$142*
Seen: 6 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $142
cmp-daily-histogram-bars-legend-max-price-aria-label $319
Displaying fares for October-2026
  • IND–MDW, 10/03/2026: From $266
    03

    Sat

    OCT

  • IND–MDW, 10/04/2026: From $319
    04

    Sun

  • IND–MDW, 10/05/2026: From $319
    05

    Mon

  • IND–MDW, 10/06/2026: From $266
    06

    Tue

  • IND–MDW, 10/07/2026: From $266
    07

    Wed

  • IND–MDW, 10/08/2026: From $319
    08

    Thu

  • IND–MDW, 10/09/2026: From $319
    09

    Fri

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

    Sat

  • IND–MDW, 10/11/2026: From $319
    11

    Sun

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

    Mon

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

    Tue

  • IND–MDW, 10/14/2026: From $266
    14

    Wed

  • IND–MDW: cmp-view-offers-disclaimer. Find Offers
    15

    Thu

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

    Fri

  • IND–MDW, 10/17/2026: From $245
    17

    Sat

  • IND–MDW, 10/18/2026: From $254
    18

    Sun

  • IND–MDW, 10/19/2026: From $245
    19

    Mon

  • IND–MDW, 10/20/2026: From $245
    20

    Tue

  • IND–MDW, 10/21/2026: From $245
    21

    Wed

  • IND–MDW, 10/22/2026: From $245
    22

    Thu

  • IND–MDW, 10/23/2026: From $168
    23

    Fri

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

    Sat

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

    Sun

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

    Mon

  • IND–MDW, 10/27/2026: From $168
    27

    Tue

  • IND–MDW, 10/28/2026: From $168
    28

    Wed

  • IND–MDW, 10/29/2026: From $168
    29

    Thu

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

    Fri

  • IND–MDW, 10/31/2026: From $168
    31

    Sat

  • IND–MDW, 11/01/2026: From $184
    01

    Sun

    NOV

  • IND–MDW, 11/02/2026: From $142
    02

    Mon

    • Range$142-$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:
    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