Southwest® flights from Little Rock to Chicago-Midway from $185

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Low fares from Little Rock to Chicago-Midway

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Little Rock (LIT)to

Chicago-Midway (MDW)
Depart: 12/14/2026

One-way

Basic

From
$185
Seen: 15 hrs ago

Little Rock (LIT)to

Chicago-Midway (MDW)
Depart: 12/16/2026

One-way

Basic

From
$185
Seen: 54 minutes ago

Little Rock (LIT)to

Chicago-Midway (MDW)
Depart: 02/04/2027

One-way

Basic

From
$185
Seen: 8 hrs ago

Little Rock (LIT)to

Chicago-Midway (MDW)
Depart: 12/30/2026

One-way

Basic

From
$185
Seen: 7 hrs ago

Little Rock (LIT)to

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

One-way

Basic

From
$190
Seen: 20 hrs ago

Little Rock (LIT)to

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

One-way

Basic

From
$190
Seen: 11 hrs ago

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Explore flights from Little Rock to Chicago-Midway

Nov 2026
From$205*
Seen: 1 hour ago
One Way/Basic
Dec 2026
From$185*
Seen: 7 hrs ago
One Way/Basic
Jan 2027
From$205*
Seen: 14 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $190
cmp-daily-histogram-bars-legend-max-price-aria-label $386
Displaying fares for November-2026
  • LIT–MDW, 11/11/2026: From $235
    11

    Wed

    NOV

  • LIT–MDW, 11/12/2026: From $276
    12

    Thu

  • LIT–MDW, 11/13/2026: From $276
    13

    Fri

  • LIT–MDW, 11/14/2026: From $240
    14

    Sat

  • LIT–MDW, 11/15/2026: From $281
    15

    Sun

  • LIT–MDW, 11/16/2026: From $276
    16

    Mon

  • LIT–MDW, 11/17/2026: From $235
    17

    Tue

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

    Wed

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

    Thu

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

    Fri

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

    Sat

  • LIT–MDW, 11/22/2026: From $240
    22

    Sun

  • LIT–MDW, 11/23/2026: From $240
    23

    Mon

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

    Tue

  • LIT–MDW, 11/25/2026: From $205
    25

    Wed

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

    Thu

  • LIT–MDW, 11/27/2026: From $300
    27

    Fri

  • LIT–MDW, 11/28/2026: From $386
    28

    Sat

  • LIT–MDW, 11/29/2026: From $353
    29

    Sun

  • LIT–MDW, 11/30/2026: From $235
    30

    Mon

  • LIT–MDW, 12/01/2026: From $205
    01

    Tue

    DEC

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

    Wed

  • LIT–MDW, 12/03/2026: From $190
    03

    Thu

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

    Fri

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

    Sat

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

    Sun

  • LIT–MDW: cmp-view-offers-disclaimer. Find Offers
    07

    Mon

  • LIT–MDW: cmp-view-offers-disclaimer. Find Offers
    08

    Tue

  • LIT–MDW: cmp-view-offers-disclaimer. Find Offers
    09

    Wed

  • LIT–MDW, 12/10/2026: From $190
    10

    Thu

    • Range$190-$386

    *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:
    Little Rock Regional Airport
    Arriving at:
    Chicago Midway International Airport
    Distance:
    544 miles

    Questions we hear the most

    There are 88 weekly flights from Little Rock to Chicago (Midway) on Southwest Airlines.
    To find the lowest fares by day and time to fly Little Rock 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 Little Rock 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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