Southwest® flights from Grand Rapids to Chicago (Midway) from $69

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Low fares from Grand Rapids to Chicago (Midway)

$

Grand Rapids (GRR)to

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

One-way

Basic

From
$69
Seen: 11 hrs ago

Grand Rapids (GRR)to

Chicago (Midway) (MDW)
Depart: 09/10/2026

One-way

Basic

From
$69
Seen: 16 hrs ago

Grand Rapids (GRR)to

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

One-way

Basic

From
$69
Seen: 6 hrs ago

Grand Rapids (GRR)to

Chicago (Midway) (MDW)
Depart: 10/15/2026

One-way

Basic

From
$69
Seen: 7 minutes ago

Grand Rapids (GRR)to

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

One-way

Basic

From
$103
Seen: 11 hrs ago

Grand Rapids (GRR)to

Chicago (Midway) (MDW)
Depart: 09/25/2026

One-way

Basic

From
$103
Seen: 5 hrs ago

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Explore flights from Grand Rapids to Chicago (Midway)

Aug 2026
From$217*
Seen: 48 minutes ago
One Way/Basic
Sep 2026
From$69*
Seen: 16 hrs ago
One Way/Basic
Oct 2026
From$69*
Seen: 7 minutes ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $69
cmp-daily-histogram-bars-legend-max-price-aria-label $266
Displaying fares for August-2026
  • GRR–MDW, 08/21/2026: From $266
    21

    Fri

    AUG

  • GRR–MDW, 08/22/2026: From $217
    22

    Sat

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

    Sun

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

    Mon

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

    Tue

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

    Wed

  • GRR–MDW, 08/27/2026: From $266
    27

    Thu

  • GRR–MDW, 08/28/2026: From $266
    28

    Fri

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

    Sat

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

    Sun

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

    Mon

  • GRR–MDW, 09/01/2026: From $217
    01

    Tue

    SEP

  • GRR–MDW, 09/02/2026: From $217
    02

    Wed

  • GRR–MDW, 09/03/2026: From $227
    03

    Thu

  • GRR–MDW, 09/04/2026: From $227
    04

    Fri

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

    Sat

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    06

    Sun

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    07

    Mon

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

    Tue

  • GRR–MDW, 09/09/2026: From $173
    09

    Wed

  • GRR–MDW, 09/10/2026: From $69
    10

    Thu

  • GRR–MDW: cmp-view-offers-disclaimer. Find Offers
    11

    Fri

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

    Sat

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    13

    Sun

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

    Mon

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

    Tue

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

    Wed

  • GRR–MDW: cmp-view-offers-disclaimer. Find Offers
    17

    Thu

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

    Fri

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

    Sat

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    20

    Sun

    • Range$69-$266

    *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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