Southwest® flights from Harlingen/South Padre Island to Chicago (O'Hare)

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Low fares from Harlingen/South Padre Island to Chicago (O'Hare)

$

Harlingen/South Padre Island (HRL)to

Chicago (Midway) (MDW)
Depart: 09/10/2026

One-way

Basic

From
$146
Seen: 5 hrs ago

Harlingen/South Padre Island (HRL)to

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

One-way

Basic

From
$146
Seen: 7 hrs ago

Harlingen/South Padre Island (HRL)to

Chicago (Midway) (MDW)
Depart: 09/23/2026

One-way

Basic

From
$156
Seen: 6 hrs ago

Harlingen/South Padre Island (HRL)to

Chicago (Midway) (MDW)
Depart: 11/04/2026

One-way

Basic

From
$156
Seen: 49 minutes ago

Harlingen/South Padre Island (HRL)to

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

One-way

Basic

From
$156
Seen: 10 hrs ago

Harlingen/South Padre Island (HRL)to

Chicago (Midway) (MDW)
Depart: 10/03/2026

One-way

Basic

From
$156
Seen: 19 hrs ago

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Explore flights from Harlingen/South Padre Island to Chicago (O'Hare)

Aug 2026
From$170*
Seen: 6 hrs ago
One Way/Basic
Sep 2026
From$146*
Seen: 5 hrs ago
One Way/Basic
Oct 2026
From$156*
Seen: 19 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $170
cmp-daily-histogram-bars-legend-max-price-aria-label $265
Displaying fares for August-2026
  • HRL–MDW, 08/05/2026: From $220
    05

    Wed

    AUG

  • HRL–MDW, 08/06/2026: From $265
    06

    Thu

  • HRL–MDW, 08/07/2026: From $222
    07

    Fri

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    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

  • HRL–MDW, 08/17/2026: From $205
    17

    Mon

  • HRL–MDW, 08/18/2026: From $185
    18

    Tue

  • HRL–MDW, 08/19/2026: From $185
    19

    Wed

  • HRL–MDW, 08/20/2026: From $205
    20

    Thu

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    21

    Fri

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    22

    Sat

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    23

    Sun

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    24

    Mon

  • HRL–MDW, 08/25/2026: From $170
    25

    Tue

  • HRL–MDW, 08/26/2026: From $170
    26

    Wed

  • HRL–MDW, 08/27/2026: From $170
    27

    Thu

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    28

    Fri

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    29

    Sat

  • HRL–MDW, 08/30/2026: From $200
    30

    Sun

  • HRL–MDW, 08/31/2026: From $170
    31

    Mon

  • HRL–MDW, 09/01/2026: From $170
    01

    Tue

    SEP

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    02

    Wed

  • HRL–MDW, 09/03/2026: From $225
    03

    Thu

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    04

    Fri

    • Range$170-$265

    *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:
    Valley International Airport
    Arriving at:
    O'Hare International Airport
    Distance:
    1219 miles

    Route Information

    49† 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 49 weekly flights from Harlingen/South Padre Island to Chicago (O'Hare) on Southwest Airlines.
    To find the lowest fares by day and time to fly Harlingen/South Padre Island 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 Harlingen/South Padre Island 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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