Southwest® flights from Fort Myers/Naples to Chicago (Midway) from $142

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Low fares from Fort Myers/Naples to Chicago (Midway)

$

Fort Myers/Naples (RSW)to

Chicago (Midway) (MDW)
Depart: 10/17/2026

One-way

Basic

From
$142
Seen: 22 hrs ago

Fort Myers/Naples (RSW)to

Chicago (Midway) (MDW)
Depart: 10/03/2026

One-way

Basic

From
$142
Seen: 17 hrs ago

Fort Myers/Naples (RSW)to

Chicago (Midway) (MDW)
Depart: 11/07/2026

One-way

Basic

From
$142
Seen: 16 hrs ago

Fort Myers/Naples (RSW)to

Chicago (Midway) (MDW)
Depart: 11/09/2026

One-way

Basic

From
$142
Seen: 17 hrs ago

Fort Myers/Naples (RSW)to

Chicago (Midway) (MDW)
Depart: 10/05/2026

One-way

Basic

From
$142
Seen: 15 hrs ago

Fort Myers/Naples (RSW)to

Chicago (Midway) (MDW)
Depart: 09/29/2026

One-way

Basic

From
$142
Seen: 6 hrs ago

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Explore flights from Fort Myers/Naples to Chicago (Midway)

Aug 2026
From$205*
Seen: 16 hrs ago
One Way/Basic
Sep 2026
From$142*
Seen: 16 hrs ago
One Way/Basic
Oct 2026
From$142*
Seen: 17 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $142
cmp-daily-histogram-bars-legend-max-price-aria-label $253
Displaying fares for August-2026
  • RSW–MDW, 08/22/2026: From $205
    22

    Sat

    AUG

  • RSW–MDW, 08/23/2026: From $253
    23

    Sun

  • RSW–MDW, 08/24/2026: From $253
    24

    Mon

  • RSW–MDW, 08/25/2026: From $205
    25

    Tue

  • RSW–MDW, 08/26/2026: From $205
    26

    Wed

  • RSW–MDW, 08/27/2026: From $253
    27

    Thu

  • RSW–MDW, 08/28/2026: From $253
    28

    Fri

  • RSW–MDW, 08/29/2026: From $205
    29

    Sat

  • RSW–MDW, 08/30/2026: From $253
    30

    Sun

  • RSW–MDW, 08/31/2026: From $253
    31

    Mon

  • RSW–MDW, 09/01/2026: From $205
    01

    Tue

    SEP

  • RSW–MDW, 09/02/2026: From $205
    02

    Wed

  • RSW–MDW, 09/03/2026: From $253
    03

    Thu

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

    Fri

  • RSW–MDW, 09/05/2026: From $180
    05

    Sat

  • RSW–MDW, 09/06/2026: From $180
    06

    Sun

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

    Mon

  • RSW–MDW, 09/08/2026: From $215
    08

    Tue

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

    Wed

  • RSW–MDW, 09/10/2026: From $180
    10

    Thu

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

    Fri

  • RSW–MDW, 09/12/2026: From $152
    12

    Sat

  • RSW–MDW, 09/13/2026: From $250
    13

    Sun

  • RSW–MDW, 09/14/2026: From $152
    14

    Mon

  • RSW–MDW, 09/15/2026: From $142
    15

    Tue

  • RSW–MDW, 09/16/2026: From $142
    16

    Wed

  • RSW–MDW, 09/17/2026: From $142
    17

    Thu

  • RSW–MDW, 09/18/2026: From $160
    18

    Fri

  • RSW–MDW, 09/19/2026: From $142
    19

    Sat

  • RSW–MDW, 09/20/2026: From $184
    20

    Sun

  • RSW–MDW, 09/21/2026: From $142
    21

    Mon

    • Range$142-$253

    *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:
    Southwest Florida Regional Airport
    Arriving at:
    Chicago Midway International Airport
    Average flight time:
    2 hours 50 minutes
    Distance:
    1105 miles

    Route Information

    155† Weekly flights
    • 2‡ Nonstop flights per day Monday through Friday
    • 3‡ 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 Fort Myers/Naples to Chicago (Midway) is 2 hours 50 minutes.
    There are 155 weekly flights from Fort Myers/Naples to Chicago (Midway) on Southwest Airlines.
    Yes, Southwest flies nonstop from Fort Myers/Naples to Chicago (Midway) 2 times per day from Monday through Friday.
    Yes, Southwest flies nonstop from Fort Myers/Naples to Chicago (Midway) 3 times per day on Saturdays and Sundays.
    To find the lowest fares by day and time to fly Fort Myers/Naples 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 Fort Myers/Naples 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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