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

Promo Code

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

$

Harlingen/South Padre Island (HRL)to

Chicago-Midway (MDW)
Depart: 10/24/2026

One-way

Basic

From
$156
Seen: 7 hrs ago

Harlingen/South Padre Island (HRL)to

Chicago-Midway (MDW)
Depart: 10/27/2026

One-way

Basic

From
$156
Seen: 6 hrs ago

Harlingen/South Padre Island (HRL)to

Chicago-Midway (MDW)
Depart: 11/07/2026

One-way

Basic

From
$156
Seen: 11 hrs ago

Harlingen/South Padre Island (HRL)to

Chicago-Midway (MDW)
Depart: 12/08/2026

One-way

Basic

From
$156
Seen: 6 hrs ago

Harlingen/South Padre Island (HRL)to

Chicago-Midway (MDW)
Depart: 12/09/2026

One-way

Basic

From
$156
Seen: 6 hrs ago

Harlingen/South Padre Island (HRL)to

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

One-way

Basic

From
$170
Seen: 19 hrs ago

Looking for more low-fare flights?

Check out the Low Fare Calendar to find a fare that works for you. Just choose the month you want to depart and return, and we’ll show you the best fares available.

Find low fares

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

Sep 2026
From$185*
Seen: 17 hrs ago
One Way/Basic
Oct 2026
From$156*
Seen: 6 hrs 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 $300
Displaying fares for September-2026
  • HRL–MDW: cmp-view-offers-disclaimer. Find Offers
    10

    Thu

    SEP

  • HRL–MDW, 09/11/2026: From $300
    11

    Fri

  • HRL–MDW, 09/12/2026: From $230
    12

    Sat

  • HRL–MDW, 09/13/2026: From $232
    13

    Sun

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

    Mon

  • HRL–MDW, 09/15/2026: From $185
    15

    Tue

  • HRL–MDW, 09/16/2026: From $185
    16

    Wed

  • HRL–MDW, 09/17/2026: From $265
    17

    Thu

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

    Fri

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

    Sat

  • HRL–MDW: cmp-view-offers-disclaimer. Find Offers
    20

    Sun

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

    Mon

  • HRL–MDW, 09/22/2026: From $185
    22

    Tue

  • HRL–MDW, 09/23/2026: From $185
    23

    Wed

  • HRL–MDW, 09/24/2026: From $205
    24

    Thu

  • HRL–MDW, 09/25/2026: From $215
    25

    Fri

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

    Sat

  • HRL–MDW: cmp-view-offers-disclaimer. Find Offers
    27

    Sun

  • HRL–MDW, 09/28/2026: From $205
    28

    Mon

  • HRL–MDW, 09/29/2026: From $185
    29

    Tue

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

    Wed

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

    Thu

    OCT

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

    Fri

  • HRL–MDW, 10/03/2026: From $170
    03

    Sat

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

    Sun

  • HRL–MDW, 10/05/2026: From $170
    05

    Mon

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

    Tue

  • HRL–MDW, 10/07/2026: From $185
    07

    Wed

  • HRL–MDW, 10/08/2026: From $259
    08

    Thu

  • HRL–MDW, 10/09/2026: From $300
    09

    Fri

    • Range$170-$300

    *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

    Route Information

    111† 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 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.

    Explore Flights from Other Popular Origins

    Popular Flights from Harlingen/South Padre Island