Southwest® flights from Bozeman to Chicago (Midway) from $168

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Low fares from Bozeman to Chicago (Midway)

$

Bozeman (BZN)to

Chicago (Midway) (MDW)
Depart: 09/24/2026

One-way

Basic

From
$168
Seen: 5 hrs ago

Bozeman (BZN)to

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

One-way

Basic

From
$168
Seen: 5 hrs ago

Bozeman (BZN)to

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

One-way

Basic

From
$173
Seen: 12 hrs ago

Bozeman (BZN)to

Chicago (Midway) (MDW)
Depart: 09/17/2026

One-way

Basic

From
$202
Seen: 13 hrs ago

Bozeman (BZN)to

Chicago (Midway) (MDW)
Depart: 09/16/2026

One-way

Basic

From
$202
Seen: 17 hrs ago

Bozeman (BZN)to

Chicago (Midway) (MDW)
Depart: 09/14/2026

One-way

Basic

From
$207
Seen: 23 hrs ago

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Explore flights from Bozeman to Chicago (Midway)

Aug 2026
From$208*
Seen: 13 hrs ago
One Way/Basic
Sep 2026
From$168*
Seen: 5 hrs ago
One Way/Basic
Oct 2026
From$215*
Seen: 1 hour ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $202
cmp-daily-histogram-bars-legend-max-price-aria-label $429
Displaying fares for August-2026
  • BZN–MDW, 08/23/2026: From $218
    23

    Sun

    AUG

  • BZN–MDW, 08/24/2026: From $218
    24

    Mon

  • BZN–MDW, 08/25/2026: From $218
    25

    Tue

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

    Wed

  • BZN–MDW, 08/27/2026: From $208
    27

    Thu

  • BZN–MDW, 08/28/2026: From $208
    28

    Fri

  • BZN–MDW, 08/29/2026: From $208
    29

    Sat

  • BZN–MDW, 08/30/2026: From $218
    30

    Sun

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

    Mon

  • BZN–MDW, 09/01/2026: From $208
    01

    Tue

    SEP

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

    Wed

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

    Thu

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    04

    Fri

  • BZN–MDW, 09/05/2026: From $208
    05

    Sat

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

    Sun

  • BZN–MDW: cmp-view-offers-disclaimer. Find Offers
    07

    Mon

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

    Tue

  • BZN–MDW, 09/09/2026: From $242
    09

    Wed

  • BZN–MDW, 09/10/2026: From $218
    10

    Thu

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

    Fri

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

    Sat

  • BZN–MDW, 09/13/2026: From $429
    13

    Sun

  • BZN–MDW, 09/14/2026: From $207
    14

    Mon

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

    Tue

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

    Wed

  • BZN–MDW, 09/17/2026: From $202
    17

    Thu

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

    Fri

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

    Sat

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

    Sun

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

    Mon

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

    Tue

    • Range$202-$429

    *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:
    Bozeman Yellowstone International Airport
    Arriving at:
    Chicago Midway International Airport
    Average flight time:
    2 hours 55 minutes
    Distance:
    1198 miles

    Route Information

    80† Weekly flights
    • 1‡ Nonstop flight per day Monday through Friday

    † 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 Bozeman to Chicago (Midway) is 2 hours 55 minutes.
    There are 80 weekly flights from Bozeman to Chicago (Midway) on Southwest Airlines.
    Yes, Southwest flies nonstop from Bozeman to Chicago (Midway) once per day from Monday through Friday.
    To find the lowest fares by day and time to fly Bozeman 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 Bozeman 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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