Southwest® flights from Chicago-Midway to Harlingen/South Padre Island from $156

Promo Code

Low fares from Chicago-Midway to Harlingen/South Padre Island

$

Chicago-Midway (MDW)to

Harlingen/South Padre Island (HRL)
Depart: 11/18/2026

One-way

Basic

From
$156
Seen: 23 hrs ago

Chicago-Midway (MDW)to

Harlingen/South Padre Island (HRL)
Depart: 10/31/2026

One-way

Basic

From
$156
Seen: 1 hour ago

Chicago-Midway (MDW)to

Harlingen/South Padre Island (HRL)
Depart: 11/10/2026

One-way

Basic

From
$156
Seen: 11 hrs ago

Chicago-Midway (MDW)to

Harlingen/South Padre Island (HRL)
Depart: 11/11/2026

One-way

Basic

From
$156
Seen: 6 hrs ago

Chicago-Midway (MDW)to

Harlingen/South Padre Island (HRL)
Depart: 12/09/2026

One-way

Basic

From
$156
Seen: 23 hrs ago

Chicago-Midway (MDW)to

Harlingen/South Padre Island (HRL)
Depart: 11/07/2026

One-way

Basic

From
$156
Seen: 19 hrs ago

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Explore flights from Chicago-Midway to Harlingen/South Padre Island

Try alternate month or interact with individual days below in order to find offers.
Sep 2026
No result for this month.
Oct 2026
From$156*
Seen: 1 hour ago
One Way/Basic
Nov 2026
From$156*
Seen: 11 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $170
cmp-daily-histogram-bars-legend-max-price-aria-label $444
Displaying fares for September-2026
  • MDW–HRL: cmp-view-offers-disclaimer. Find Offers
    30

    Wed

    SEP

  • MDW–HRL, 10/01/2026: From $232
    01

    Thu

  • MDW–HRL, 10/02/2026: From $232
    02

    Fri

  • MDW–HRL, 10/03/2026: From $200
    03

    Sat

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

    Sun

  • MDW–HRL, 10/05/2026: From $232
    05

    Mon

  • MDW–HRL, 10/06/2026: From $195
    06

    Tue

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

    Wed

  • MDW–HRL, 10/08/2026: From $232
    08

    Thu

  • MDW–HRL, 10/09/2026: From $275
    09

    Fri

  • MDW–HRL, 10/10/2026: From $195
    10

    Sat

  • MDW–HRL, 10/11/2026: From $275
    11

    Sun

  • MDW–HRL, 10/12/2026: From $444
    12

    Mon

  • MDW–HRL, 10/13/2026: From $260
    13

    Tue

  • MDW–HRL, 10/14/2026: From $195
    14

    Wed

  • MDW–HRL, 10/15/2026: From $250
    15

    Thu

  • MDW–HRL, 10/16/2026: From $250
    16

    Fri

  • MDW–HRL: cmp-view-offers-disclaimer. Find Offers
    17

    Sat

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

    Sun

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

    Mon

  • MDW–HRL, 10/20/2026: From $210
    20

    Tue

  • MDW–HRL, 10/21/2026: From $170
    21

    Wed

  • MDW–HRL, 10/22/2026: From $170
    22

    Thu

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

    Fri

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

    Sat

  • MDW–HRL, 10/25/2026: From $195
    25

    Sun

  • MDW–HRL, 10/26/2026: From $195
    26

    Mon

  • MDW–HRL, 10/27/2026: From $170
    27

    Tue

  • MDW–HRL, 10/28/2026: From $170
    28

    Wed

  • MDW–HRL, 10/29/2026: From $170
    29

    Thu

    • Range$170-$444

    *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:
    Chicago Midway International Airport
    Arriving at:
    Valley International Airport
    Distance:
    1212 miles

    Route Information

    98† 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 98 weekly flights from Chicago (Midway) to Harlingen/South Padre Island on Southwest Airlines.
    To find the lowest fares by day and time to fly Chicago (Midway) to Harlingen/South Padre Island with Southwest, check out our Low Fare Calendar.
    You can rent a car at Valley International Airport book yours with your flight.
    Yes! Flights from Chicago (Midway) to Harlingen/South Padre Island—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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