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: 10/13/2026

One-way

Basic

From
$150
Seen: 12 hrs ago

Little Rock (LIT)to

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

One-way

Basic

From
$150
Seen: 5 hrs ago

Little Rock (LIT)to

Chicago (Midway) (MDW)
Depart: 09/21/2026

One-way

Basic

From
$150
Seen: 3 hrs ago

Little Rock (LIT)to

Chicago (Midway) (MDW)
Depart: 10/01/2026

One-way

Basic

From
$150
Seen: 3 hrs ago

Little Rock (LIT)to

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

One-way

Basic

From
$150
Seen: 7 hrs ago

Little Rock (LIT)to

Chicago (Midway) (MDW)
Depart: 10/23/2026

One-way

Basic

From
$150
Seen: 3 hrs ago

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

Aug 2026
From$200*
Seen: 23 hrs ago
One Way/Basic
Sep 2026
From$150*
Seen: 23 hrs ago
One Way/Basic
Oct 2026
From$150*
Seen: 11 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $150
cmp-daily-histogram-bars-legend-max-price-aria-label $260
Displaying fares for August-2026
  • LIT–MDW, 08/25/2026: From $200
    25

    Tue

    AUG

  • LIT–MDW, 08/26/2026: From $200
    26

    Wed

  • LIT–MDW, 08/27/2026: From $241
    27

    Thu

  • LIT–MDW, 08/28/2026: From $241
    28

    Fri

  • LIT–MDW, 08/29/2026: From $200
    29

    Sat

  • LIT–MDW, 08/30/2026: From $241
    30

    Sun

  • LIT–MDW, 08/31/2026: From $205
    31

    Mon

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

    Tue

    SEP

  • LIT–MDW, 09/02/2026: From $200
    02

    Wed

  • LIT–MDW, 09/03/2026: From $246
    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, 09/07/2026: From $260
    07

    Mon

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

    Tue

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

    Wed

  • LIT–MDW, 09/10/2026: From $166
    10

    Thu

  • LIT–MDW: cmp-view-offers-disclaimer. Find Offers
    11

    Fri

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

    Sat

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

    Sun

  • LIT–MDW, 09/14/2026: From $150
    14

    Mon

  • LIT–MDW, 09/15/2026: From $150
    15

    Tue

  • LIT–MDW, 09/16/2026: From $168
    16

    Wed

  • LIT–MDW, 09/17/2026: From $150
    17

    Thu

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

    Fri

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

    Sat

  • LIT–MDW, 09/20/2026: From $189
    20

    Sun

  • LIT–MDW, 09/21/2026: From $150
    21

    Mon

  • LIT–MDW, 09/22/2026: From $150
    22

    Tue

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

    Wed

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

    Thu

    • Range$150-$260

    *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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