Southwest® flights from Miami to Chicago (O'Hare)

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Low fares from Miami to Chicago (O'Hare)

$

Miami (MIA)to

Chicago (Midway) (MDW)
Depart: 10/29/2026

One-way

Basic

From
$86
Seen: 4 hrs ago

Miami (MIA)to

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

One-way

Basic

From
$86
Seen: 2 hrs ago

Miami (MIA)to

Chicago (Midway) (MDW)
Depart: 09/15/2026

One-way

Basic

From
$86
Seen: 2 hrs ago

Miami (MIA)to

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

One-way

Basic

From
$86
Seen: 13 hrs ago

Miami (MIA)to

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

One-way

Basic

From
$86
Seen: 16 hrs ago

Miami (MIA)to

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

One-way

Basic

From
$86
Seen: 12 hrs ago

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Explore flights from Miami to Chicago (O'Hare)

Aug 2026
From$247*
Seen: 19 hrs ago
One Way/Basic
Sep 2026
From$86*
Seen: 13 hrs ago
One Way/Basic
Oct 2026
From$86*
Seen: 10 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $86
cmp-daily-histogram-bars-legend-max-price-aria-label $318
Displaying fares for August-2026
  • MIA–MDW, 08/19/2026: From $247
    19

    Wed

    AUG

  • MIA–MDW, 08/20/2026: From $318
    20

    Thu

  • MIA–MDW, 08/21/2026: From $318
    21

    Fri

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

    Sat

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

    Sun

  • MIA–MDW, 08/24/2026: From $318
    24

    Mon

  • MIA–MDW, 08/25/2026: From $247
    25

    Tue

  • MIA–MDW, 08/26/2026: From $247
    26

    Wed

  • MIA–MDW, 08/27/2026: From $318
    27

    Thu

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

    Fri

  • MIA–MDW, 08/29/2026: From $247
    29

    Sat

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

    Sun

  • MIA–MDW, 08/31/2026: From $318
    31

    Mon

  • MIA–MDW, 09/01/2026: From $247
    01

    Tue

    SEP

  • MIA–MDW, 09/02/2026: From $247
    02

    Wed

  • MIA–MDW, 09/03/2026: From $282
    03

    Thu

  • MIA–MDW, 09/04/2026: From $282
    04

    Fri

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    05

    Sat

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

    Sun

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

    Mon

  • MIA–MDW, 09/08/2026: From $96
    08

    Tue

  • MIA–MDW: cmp-view-offers-disclaimer. Find Offers
    09

    Wed

  • MIA–MDW, 09/10/2026: From $86
    10

    Thu

  • MIA–MDW, 09/11/2026: From $96
    11

    Fri

  • MIA–MDW, 09/12/2026: From $101
    12

    Sat

  • MIA–MDW, 09/13/2026: From $260
    13

    Sun

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

    Mon

  • MIA–MDW, 09/15/2026: From $86
    15

    Tue

  • MIA–MDW, 09/16/2026: From $86
    16

    Wed

  • MIA–MDW, 09/17/2026: From $86
    17

    Thu

  • MIA–MDW, 09/18/2026: From $96
    18

    Fri

    • Range$86-$318

    *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:
    Miami International Airport
    Arriving at:
    O'Hare International Airport
    Distance:
    1197 miles

    Route Information

    35† 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 35 weekly flights from Miami to Chicago (O'Hare) on Southwest Airlines.
    To find the lowest fares by day and time to fly Miami to Chicago (O'Hare) with Southwest, check out our Low Fare Calendar.
    You can rent a car at O'Hare International Airport book yours with your flight.
    Yes! Flights from Miami to Chicago (O'Hare)—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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