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: 09/05/2026

One-way

Basic

From
$142
Seen: 1 hour ago

Fort Myers/Naples (RSW)to

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

One-way

Basic

From
$142
Seen: 7 minutes ago

Fort Myers/Naples (RSW)to

Chicago (Midway) (MDW)
Depart: 10/19/2026

One-way

Basic

From
$153
Seen: 7 hrs ago

Fort Myers/Naples (RSW)to

Chicago (Midway) (MDW)
Depart: 09/26/2026

One-way

Basic

From
$153
Seen: 3 hrs ago

Fort Myers/Naples (RSW)to

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

One-way

Basic

From
$153
Seen: 6 hrs ago

Fort Myers/Naples (RSW)to

Chicago (Midway) (MDW)
Depart: 10/28/2026

One-way

Basic

From
$153
Seen: 10 hrs ago

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

Aug 2026
From$153*
Seen: 4 hrs ago
One Way/Basic
Sep 2026
From$142*
Seen: 1 hour ago
One Way/Basic
Oct 2026
From$153*
Seen: 7 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $153
cmp-daily-histogram-bars-legend-max-price-aria-label $253
Displaying fares for August-2026
  • RSW–MDW, 08/02/2026: From $253
    02

    Sun

    AUG

  • RSW–MDW, 08/03/2026: From $253
    03

    Mon

  • RSW–MDW, 08/04/2026: From $215
    04

    Tue

  • RSW–MDW, 08/05/2026: From $215
    05

    Wed

  • RSW–MDW, 08/06/2026: From $253
    06

    Thu

  • RSW–MDW, 08/07/2026: From $253
    07

    Fri

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

    Sat

  • RSW–MDW, 08/09/2026: From $253
    09

    Sun

  • RSW–MDW, 08/10/2026: From $253
    10

    Mon

  • RSW–MDW, 08/11/2026: From $205
    11

    Tue

  • RSW–MDW, 08/12/2026: From $205
    12

    Wed

  • RSW–MDW, 08/13/2026: From $253
    13

    Thu

  • RSW–MDW, 08/14/2026: From $253
    14

    Fri

  • RSW–MDW, 08/15/2026: From $215
    15

    Sat

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

    Sun

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

    Mon

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

    Tue

  • RSW–MDW, 08/19/2026: From $205
    19

    Wed

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

    Thu

  • RSW–MDW, 08/21/2026: From $172
    21

    Fri

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

    Sat

  • RSW–MDW, 08/23/2026: From $250
    23

    Sun

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

    Mon

  • RSW–MDW, 08/25/2026: From $160
    25

    Tue

  • RSW–MDW, 08/26/2026: From $160
    26

    Wed

  • RSW–MDW, 08/27/2026: From $160
    27

    Thu

  • RSW–MDW, 08/28/2026: From $172
    28

    Fri

  • RSW–MDW, 08/29/2026: From $160
    29

    Sat

  • RSW–MDW, 08/30/2026: From $184
    30

    Sun

  • RSW–MDW, 08/31/2026: From $153
    31

    Mon

  • RSW–MDW, 09/01/2026: From $153
    01

    Tue

    SEP

    • Range$153-$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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