Southwest® flights from Harlingen/South Padre Island to Chicago-Midway from $171

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

$

Harlingen/South Padre Island (HRL)to

Chicago-Midway (MDW)
Depart: 01/13/2027

One-way

Basic

From
$171
Seen: 4 hrs ago

Harlingen/South Padre Island (HRL)to

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

One-way

Basic

From
$176
Seen: 9 hrs ago

Harlingen/South Padre Island (HRL)to

Chicago-Midway (MDW)
Depart: 01/18/2027

One-way

Basic

From
$185
Seen: 19 hrs ago

Harlingen/South Padre Island (HRL)to

Chicago-Midway (MDW)
Depart: 01/12/2027

One-way

Basic

From
$206
Seen: 4 hrs ago

Harlingen/South Padre Island (HRL)to

Chicago-Midway (MDW)
Depart: 12/15/2026

One-way

Basic

From
$211
Seen: 12 hrs ago

Harlingen/South Padre Island (HRL)to

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

One-way

Basic

From
$215
Seen: 22 hrs ago

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

Nov 2026
From$215*
Seen: 22 hrs ago
One Way/Basic
Dec 2026
From$176*
Seen: 9 hrs ago
One Way/Basic
Jan 2027
From$171*
Seen: 4 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $176
cmp-daily-histogram-bars-legend-max-price-aria-label $325
Displaying fares for November-2026
  • HRL–MDW: cmp-view-offers-disclaimer. Find Offers
    09

    Mon

    NOV

  • HRL–MDW, 11/10/2026: From $215
    10

    Tue

  • HRL–MDW, 11/11/2026: From $244
    11

    Wed

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

    Thu

  • HRL–MDW, 11/13/2026: From $252
    13

    Fri

  • HRL–MDW, 11/14/2026: From $284
    14

    Sat

  • HRL–MDW, 11/15/2026: From $321
    15

    Sun

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

    Mon

  • HRL–MDW, 11/17/2026: From $221
    17

    Tue

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

    Wed

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

    Thu

  • HRL–MDW, 11/20/2026: From $310
    20

    Fri

  • HRL–MDW, 11/21/2026: From $255
    21

    Sat

  • HRL–MDW: cmp-view-offers-disclaimer. Find Offers
    22

    Sun

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

    Mon

  • HRL–MDW, 11/24/2026: From $255
    24

    Tue

  • HRL–MDW, 11/25/2026: From $239
    25

    Wed

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

    Thu

  • HRL–MDW, 11/27/2026: From $325
    27

    Fri

  • HRL–MDW: cmp-view-offers-disclaimer. Find Offers
    28

    Sat

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

    Sun

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

    Mon

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

    Tue

    DEC

  • HRL–MDW, 12/02/2026: From $176
    02

    Wed

  • HRL–MDW, 12/03/2026: From $246
    03

    Thu

  • HRL–MDW, 12/04/2026: From $220
    04

    Fri

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    05

    Sat

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    06

    Sun

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    07

    Mon

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

    Tue

    • Range$176-$325

    *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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