Southwest® flights from Grand Rapids to Chicago-Midway from $129

Promo Code

Low fares from Grand Rapids to Chicago-Midway

$

Grand Rapids (GRR)to

Chicago-Midway (MDW)
Depart: 11/16/2026

One-way

Basic

From
$129
Seen: 14 hrs ago

Grand Rapids (GRR)to

Chicago-Midway (MDW)
Depart: 10/22/2026

One-way

Basic

From
$129
Seen: 3 hrs ago

Grand Rapids (GRR)to

Chicago-Midway (MDW)
Depart: 10/20/2026

One-way

Basic

From
$129
Seen: 18 hrs ago

Grand Rapids (GRR)to

Chicago-Midway (MDW)
Depart: 11/12/2026

One-way

Basic

From
$129
Seen: 16 hrs ago

Grand Rapids (GRR)to

Chicago-Midway (MDW)
Depart: 11/14/2026

One-way

Basic

From
$129
Seen: 35 minutes ago

Grand Rapids (GRR)to

Chicago-Midway (MDW)
Depart: 10/26/2026

One-way

Basic

From
$129
Seen: 16 hrs ago

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Explore flights from Grand Rapids to Chicago-Midway

Oct 2026
From$129*
Seen: 3 hrs ago
One Way/Basic
Nov 2026
From$129*
Seen: 16 hrs ago
One Way/Basic
Dec 2026
From$129*
Seen: 22 minutes ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $129
cmp-daily-histogram-bars-legend-max-price-aria-label $286
Displaying fares for October-2026
  • GRR–MDW, 10/01/2026: From $286
    01

    Thu

    OCT

  • GRR–MDW, 10/02/2026: From $286
    02

    Fri

  • GRR–MDW, 10/03/2026: From $237
    03

    Sat

  • GRR–MDW, 10/04/2026: From $286
    04

    Sun

  • GRR–MDW, 10/05/2026: From $286
    05

    Mon

  • GRR–MDW, 10/06/2026: From $237
    06

    Tue

  • GRR–MDW, 10/07/2026: From $237
    07

    Wed

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

    Thu

  • GRR–MDW, 10/09/2026: From $286
    09

    Fri

  • GRR–MDW: cmp-view-offers-disclaimer. Find Offers
    10

    Sat

  • GRR–MDW, 10/11/2026: From $286
    11

    Sun

  • GRR–MDW, 10/12/2026: From $286
    12

    Mon

  • GRR–MDW: cmp-view-offers-disclaimer. Find Offers
    13

    Tue

  • GRR–MDW, 10/14/2026: From $237
    14

    Wed

  • GRR–MDW, 10/15/2026: From $247
    15

    Thu

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

    Fri

  • GRR–MDW, 10/17/2026: From $237
    17

    Sat

  • GRR–MDW, 10/18/2026: From $247
    18

    Sun

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

    Mon

  • GRR–MDW, 10/20/2026: From $129
    20

    Tue

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

    Wed

  • GRR–MDW, 10/22/2026: From $129
    22

    Thu

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

    Fri

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

    Sat

  • GRR–MDW, 10/25/2026: From $196
    25

    Sun

  • GRR–MDW, 10/26/2026: From $129
    26

    Mon

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

    Tue

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

    Wed

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

    Thu

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

    Fri

  • GRR–MDW: cmp-view-offers-disclaimer. Find Offers
    31

    Sat

    • Range$129-$286

    *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:
    Kent County International Airport
    Arriving at:
    Chicago Midway International Airport
    Average flight time:
    1 hour 3 minutes
    Distance:
    137 miles

    Route Information

    29† Weekly flights
    • 3‡ Nonstop flights per day Monday through Friday
    • 2‡ Nonstop flights on Saturday
    • 3‡ Nonstop flights on Sunday

    † 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

    The average flight time from Grand Rapids to Chicago (Midway) is 1 hour 3 minutes.
    There are 29 weekly flights from Grand Rapids to Chicago (Midway) on Southwest Airlines.
    Yes, Southwest flies nonstop from Grand Rapids to Chicago (Midway) 3 times per day from Monday through Friday.
    Yes, Southwest flies nonstop from Grand Rapids to Chicago (Midway) 2 times per day on Saturdays and 3 times per day on Sundays.
    To find the lowest fares by day and time to fly Grand Rapids 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 Grand Rapids 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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