Southwest® flights from Harlingen/South Padre Island to Chicago-Midway from $110

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

$

Harlingen/South Padre Island (HRL)to

Chicago-Midway (MDW)
Depart: 12/02/2026

One-way

Basic

From
$110
Seen: 4 hrs ago

Harlingen/South Padre Island (HRL)to

Chicago-Midway (MDW)
Depart: 12/22/2026

One-way

Basic

From
$110
Seen: 1 hour ago

Harlingen/South Padre Island (HRL)to

Chicago-Midway (MDW)
Depart: 11/10/2026

One-way

Basic

From
$118
Seen: 2 hrs ago

Harlingen/South Padre Island (HRL)to

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

One-way

Basic

From
$118
Seen: 14 hrs ago

Harlingen/South Padre Island (HRL)to

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

One-way

Basic

From
$118
Seen: 23 hrs ago

Harlingen/South Padre Island (HRL)to

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

One-way

Basic

From
$118
Seen: 2 hrs ago

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

Oct 2026
From$205*
Seen: 11 hrs ago
One Way/Basic
Nov 2026
From$118*
Seen: 14 hrs ago
One Way/Basic
Dec 2026
From$110*
Seen: 1 hour ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $118
cmp-daily-histogram-bars-legend-max-price-aria-label $275
Displaying fares for October-2026
  • HRL–MDW, 10/20/2026: From $265
    20

    Tue

    OCT

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

    Wed

  • HRL–MDW, 10/22/2026: From $242
    22

    Thu

  • HRL–MDW, 10/23/2026: From $275
    23

    Fri

  • HRL–MDW, 10/24/2026: From $205
    24

    Sat

  • HRL–MDW: cmp-view-offers-disclaimer. Find Offers
    25

    Sun

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

    Mon

  • HRL–MDW, 10/27/2026: From $205
    27

    Tue

  • HRL–MDW, 10/28/2026: From $205
    28

    Wed

  • HRL–MDW: cmp-view-offers-disclaimer. Find Offers
    29

    Thu

  • HRL–MDW: cmp-view-offers-disclaimer. Find Offers
    30

    Fri

  • HRL–MDW, 10/31/2026: From $205
    31

    Sat

  • HRL–MDW, 11/01/2026: From $255
    01

    Sun

    NOV

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

    Mon

  • HRL–MDW, 11/03/2026: From $205
    03

    Tue

  • HRL–MDW, 11/04/2026: From $205
    04

    Wed

  • HRL–MDW, 11/05/2026: From $220
    05

    Thu

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

    Fri

  • HRL–MDW, 11/07/2026: From $205
    07

    Sat

  • HRL–MDW, 11/08/2026: From $220
    08

    Sun

  • HRL–MDW, 11/09/2026: From $118
    09

    Mon

  • HRL–MDW, 11/10/2026: From $118
    10

    Tue

  • HRL–MDW, 11/11/2026: From $118
    11

    Wed

  • HRL–MDW, 11/12/2026: From $145
    12

    Thu

  • HRL–MDW, 11/13/2026: From $210
    13

    Fri

  • HRL–MDW: cmp-view-offers-disclaimer. Find Offers
    14

    Sat

  • HRL–MDW: cmp-view-offers-disclaimer. Find Offers
    15

    Sun

  • HRL–MDW: cmp-view-offers-disclaimer. Find Offers
    16

    Mon

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    17

    Tue

  • HRL–MDW, 11/18/2026: From $166
    18

    Wed

  • HRL–MDW, 11/19/2026: From $255
    19

    Thu

    • Range$118-$275

    *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:
    Chicago Midway International Airport
    Distance:
    1212 miles

    Questions we hear the most

    There are 111 weekly flights from Harlingen/South Padre Island to Chicago (Midway) on Southwest Airlines.
    To find the lowest fares by day and time to fly Harlingen/South Padre Island 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 Harlingen/South Padre Island 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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