Southwest® flights from Greenville-Spartanburg to Chicago-Midway from $160

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Low fares from Greenville-Spartanburg to Chicago-Midway

$

Greenville-Spartanburg (GSP)to

Chicago-Midway (MDW)
Depart: 10/06/2026

One-way

Basic

From
$160
Seen: 22 hrs ago

Greenville-Spartanburg (GSP)to

Chicago-Midway (MDW)
Depart: 10/16/2026

One-way

Basic

From
$160
Seen: 23 hrs ago

Greenville-Spartanburg (GSP)to

Chicago-Midway (MDW)
Depart: 11/06/2026

One-way

Basic

From
$160
Seen: 7 hrs ago

Greenville-Spartanburg (GSP)to

Chicago-Midway (MDW)
Depart: 10/07/2026

One-way

Basic

From
$160
Seen: 1 hour ago

Greenville-Spartanburg (GSP)to

Chicago-Midway (MDW)
Depart: 11/05/2026

One-way

Basic

From
$160
Seen: 4 hrs ago

Greenville-Spartanburg (GSP)to

Chicago-Midway (MDW)
Depart: 09/30/2026

One-way

Basic

From
$160
Seen: 15 hrs ago

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Explore flights from Greenville-Spartanburg to Chicago-Midway

Sep 2026
From$160*
Seen: 15 hrs ago
One Way/Basic
Oct 2026
From$160*
Seen: 11 hrs ago
One Way/Basic
Nov 2026
From$160*
Seen: 20 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $160
cmp-daily-histogram-bars-legend-max-price-aria-label $269
Displaying fares for September-2026
  • GSP–MDW, 09/10/2026: From $257
    10

    Thu

    SEP

  • GSP–MDW, 09/11/2026: From $257
    11

    Fri

  • GSP–MDW, 09/12/2026: From $202
    12

    Sat

  • GSP–MDW, 09/13/2026: From $202
    13

    Sun

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

    Mon

  • GSP–MDW, 09/15/2026: From $202
    15

    Tue

  • GSP–MDW, 09/16/2026: From $202
    16

    Wed

  • GSP–MDW, 09/17/2026: From $215
    17

    Thu

  • GSP–MDW, 09/18/2026: From $215
    18

    Fri

  • GSP–MDW, 09/19/2026: From $200
    19

    Sat

  • GSP–MDW, 09/20/2026: From $269
    20

    Sun

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

    Mon

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

    Tue

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

    Wed

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

    Thu

  • GSP–MDW, 09/25/2026: From $180
    25

    Fri

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

    Sat

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

    Sun

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

    Mon

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

    Tue

  • GSP–MDW, 09/30/2026: From $160
    30

    Wed

  • GSP–MDW, 10/01/2026: From $160
    01

    Thu

    OCT

  • GSP–MDW, 10/02/2026: From $160
    02

    Fri

  • GSP–MDW: cmp-view-offers-disclaimer. Find Offers
    03

    Sat

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

    Sun

  • GSP–MDW: cmp-view-offers-disclaimer. Find Offers
    05

    Mon

  • GSP–MDW, 10/06/2026: From $160
    06

    Tue

  • GSP–MDW, 10/07/2026: From $160
    07

    Wed

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

    Thu

  • GSP–MDW, 10/09/2026: From $190
    09

    Fri

    • Range$160-$269

    *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:
    Greenville-Spartanburg International Airport
    Arriving at:
    Chicago Midway International Airport
    Distance:
    562 miles

    Route Information

    76† 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 76 weekly flights from Greenville-Spartanburg to Chicago (Midway) on Southwest Airlines.
    To find the lowest fares by day and time to fly Greenville-Spartanburg 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 Greenville-Spartanburg 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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