Southwest® flights from Grand Rapids to Chicago-Midway from $140

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Low fares from Grand Rapids to Chicago-Midway

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Grand Rapids (GRR)to

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

One-way

Basic

From
$140
Seen: 21 hrs ago

Grand Rapids (GRR)to

Chicago-Midway (MDW)
Depart: 12/23/2026

One-way

Basic

From
$140
Seen: 6 hrs ago

Grand Rapids (GRR)to

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

One-way

Basic

From
$140
Seen: 3 hrs ago

Grand Rapids (GRR)to

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

One-way

Basic

From
$140
Seen: 18 hrs ago

Grand Rapids (GRR)to

Chicago-Midway (MDW)
Depart: 12/01/2026

One-way

Basic

From
$140
Seen: 18 hrs ago

Grand Rapids (GRR)to

Chicago-Midway (MDW)
Depart: 12/22/2026

One-way

Basic

From
$140
Seen: 6 hrs ago

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Explore flights from Grand Rapids to Chicago-Midway

Nov 2026
From$252*
Seen: 5 hrs ago
One Way/Basic
Dec 2026
From$140*
Seen: 18 hrs ago
One Way/Basic
Jan 2027
From$155*
Seen: 11 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $140
cmp-daily-histogram-bars-legend-max-price-aria-label $301
Displaying fares for November-2026
  • GRR–MDW: cmp-view-offers-disclaimer. Find Offers
    10

    Tue

    NOV

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

    Wed

  • GRR–MDW, 11/12/2026: From $301
    12

    Thu

  • GRR–MDW, 11/13/2026: From $301
    13

    Fri

  • GRR–MDW, 11/14/2026: From $252
    14

    Sat

  • GRR–MDW, 11/15/2026: From $301
    15

    Sun

  • GRR–MDW, 11/16/2026: From $301
    16

    Mon

  • GRR–MDW, 11/17/2026: From $252
    17

    Tue

  • GRR–MDW, 11/18/2026: From $252
    18

    Wed

  • GRR–MDW, 11/19/2026: From $301
    19

    Thu

  • GRR–MDW, 11/20/2026: From $301
    20

    Fri

  • GRR–MDW, 11/21/2026: From $252
    21

    Sat

  • GRR–MDW, 11/22/2026: From $301
    22

    Sun

  • GRR–MDW, 11/23/2026: From $262
    23

    Mon

  • GRR–MDW, 11/24/2026: From $252
    24

    Tue

  • GRR–MDW, 11/25/2026: From $252
    25

    Wed

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

    Thu

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

    Fri

  • GRR–MDW, 11/28/2026: From $252
    28

    Sat

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

    Sun

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

    Mon

  • GRR–MDW, 12/01/2026: From $140
    01

    Tue

    DEC

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

    Wed

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

    Thu

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

    Fri

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

    Sat

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

    Sun

  • GRR–MDW, 12/07/2026: From $155
    07

    Mon

  • GRR–MDW, 12/08/2026: From $140
    08

    Tue

  • GRR–MDW, 12/09/2026: From $140
    09

    Wed

    • Range$140-$301

    *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

    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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