Southwest® flights from Little Rock to Chicago (O'Hare)

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Low fares from Little Rock to Chicago (O'Hare)

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Little Rock (LIT)to

Chicago (Midway) (MDW)
Depart: 08/27/2026

One-way

Basic

From
$137
Seen: 13 hrs ago

Little Rock (LIT)to

Chicago (Midway) (MDW)
Depart: 08/26/2026

One-way

Basic

From
$137
Seen: 7 hrs ago

Little Rock (LIT)to

Chicago (Midway) (MDW)
Depart: 09/04/2026

One-way

Basic

From
$137
Seen: 7 hrs ago

Little Rock (LIT)to

Chicago (Midway) (MDW)
Depart: 09/22/2026

One-way

Basic

From
$137
Seen: 43 minutes ago

Little Rock (LIT)to

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

One-way

Basic

From
$137
Seen: 8 hrs ago

Little Rock (LIT)to

Chicago (Midway) (MDW)
Depart: 08/29/2026

One-way

Basic

From
$137
Seen: 7 hrs ago

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Explore flights from Little Rock to Chicago (O'Hare)

Aug 2026
From$137*
Seen: 13 hrs ago
One Way/Basic
Sep 2026
From$137*
Seen: 8 hrs ago
One Way/Basic
Oct 2026
From$150*
Seen: 23 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $137
cmp-daily-histogram-bars-legend-max-price-aria-label $210
Displaying fares for August-2026
  • LIT–MDW, 08/05/2026: From $200
    05

    Wed

    AUG

  • LIT–MDW, 08/06/2026: From $182
    06

    Thu

  • LIT–MDW, 08/07/2026: From $182
    07

    Fri

  • LIT–MDW, 08/08/2026: From $200
    08

    Sat

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    09

    Sun

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    10

    Mon

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    11

    Tue

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    12

    Wed

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    13

    Thu

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    14

    Fri

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    15

    Sat

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    16

    Sun

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    17

    Mon

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    18

    Tue

  • LIT–MDW, 08/19/2026: From $155
    19

    Wed

  • LIT–MDW, 08/20/2026: From $155
    20

    Thu

  • LIT–MDW, 08/21/2026: From $155
    21

    Fri

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    22

    Sat

  • LIT–MDW, 08/23/2026: From $182
    23

    Sun

  • LIT–MDW, 08/24/2026: From $155
    24

    Mon

  • LIT–MDW, 08/25/2026: From $137
    25

    Tue

  • LIT–MDW, 08/26/2026: From $137
    26

    Wed

  • LIT–MDW, 08/27/2026: From $137
    27

    Thu

  • LIT–MDW, 08/28/2026: From $137
    28

    Fri

  • LIT–MDW, 08/29/2026: From $137
    29

    Sat

  • LIT–MDW, 08/30/2026: From $137
    30

    Sun

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    31

    Mon

  • LIT–MDW, 09/01/2026: From $150
    01

    Tue

    SEP

  • LIT–MDW, 09/02/2026: From $137
    02

    Wed

  • LIT–MDW, 09/03/2026: From $210
    03

    Thu

  • LIT–MDW, 09/04/2026: From $137
    04

    Fri

    • Range$137-$210

    *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:
    O'Hare International Airport
    Distance:
    552 miles

    Route Information

    52† 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 52 weekly flights from Little Rock to Chicago (O'Hare) on Southwest Airlines.
    To find the lowest fares by day and time to fly Little Rock 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 Little Rock 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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