Southwest® flights from Chicago-Midway to Fort Myers/Naples from $116

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Low fares from Chicago-Midway to Fort Myers/Naples

$

Chicago-Midway (MDW)to

Fort Myers/Naples (RSW)
Depart: 11/10/2026

One-way

Basic

From
$116
Seen: 22 hrs ago

Chicago-Midway (MDW)to

Fort Myers/Naples (RSW)
Depart: 12/07/2026

One-way

Basic

From
$116
Seen: 17 hrs ago

Chicago-Midway (MDW)to

Fort Myers/Naples (RSW)
Depart: 11/14/2026

One-way

Basic

From
$116
Seen: 18 hrs ago

Chicago-Midway (MDW)to

Fort Myers/Naples (RSW)
Depart: 01/27/2027

One-way

Basic

From
$116
Seen: 7 hrs ago

Chicago-Midway (MDW)to

Fort Myers/Naples (RSW)
Depart: 11/12/2026

One-way

Basic

From
$116
Seen: 19 hrs ago

Chicago-Midway (MDW)to

Fort Myers/Naples (RSW)
Depart: 12/02/2026

One-way

Basic

From
$116
Seen: 18 hrs ago

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Explore flights from Chicago-Midway to Fort Myers/Naples

Oct 2026
From$228*
Seen: 17 hrs ago
One Way/Basic
Nov 2026
From$116*
Seen: 19 hrs ago
One Way/Basic
Dec 2026
From$116*
Seen: 3 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $116
cmp-daily-histogram-bars-legend-max-price-aria-label $350
Displaying fares for October-2026
  • MDW–RSW, 10/22/2026: From $350
    22

    Thu

    OCT

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

    Fri

  • MDW–RSW, 10/24/2026: From $228
    24

    Sat

  • MDW–RSW: cmp-view-offers-disclaimer. Find Offers
    25

    Sun

  • MDW–RSW, 10/26/2026: From $283
    26

    Mon

  • MDW–RSW, 10/27/2026: From $228
    27

    Tue

  • MDW–RSW, 10/28/2026: From $228
    28

    Wed

  • MDW–RSW, 10/29/2026: From $283
    29

    Thu

  • MDW–RSW, 10/30/2026: From $283
    30

    Fri

  • MDW–RSW, 10/31/2026: From $238
    31

    Sat

  • MDW–RSW, 11/01/2026: From $283
    01

    Sun

    NOV

  • MDW–RSW, 11/02/2026: From $283
    02

    Mon

  • MDW–RSW, 11/03/2026: From $228
    03

    Tue

  • MDW–RSW, 11/04/2026: From $228
    04

    Wed

  • MDW–RSW, 11/05/2026: From $283
    05

    Thu

  • MDW–RSW, 11/06/2026: From $283
    06

    Fri

  • MDW–RSW, 11/07/2026: From $228
    07

    Sat

  • MDW–RSW, 11/08/2026: From $283
    08

    Sun

  • MDW–RSW, 11/09/2026: From $116
    09

    Mon

  • MDW–RSW, 11/10/2026: From $116
    10

    Tue

  • MDW–RSW, 11/11/2026: From $131
    11

    Wed

  • MDW–RSW, 11/12/2026: From $116
    12

    Thu

  • MDW–RSW, 11/13/2026: From $147
    13

    Fri

  • MDW–RSW, 11/14/2026: From $116
    14

    Sat

  • MDW–RSW, 11/15/2026: From $147
    15

    Sun

  • MDW–RSW, 11/16/2026: From $116
    16

    Mon

  • MDW–RSW, 11/17/2026: From $116
    17

    Tue

  • MDW–RSW, 11/18/2026: From $126
    18

    Wed

  • MDW–RSW, 11/19/2026: From $280
    19

    Thu

  • MDW–RSW, 11/20/2026: From $298
    20

    Fri

  • MDW–RSW, 11/21/2026: From $284
    21

    Sat

    • Range$116-$350

    *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:
    Chicago Midway International Airport
    Arriving at:
    Southwest Florida Regional Airport
    Average flight time:
    2 hours 40 minutes
    Distance:
    1105 miles

    Explore Fort Myers/Naples

    Known as a gateway for Southwest Florida, Fort Myers is just a 20-minute drive northwest from Southwest Florida International Airport. Famed for its golf courses, deep-sea fishing, and exquisite white sand beaches, Fort Myers is a top destination for tourists, and it's easy to see why.

    When you travel to Fort Myers, you can delve into the minds and accomplishments of two titans of American industry: Inventor Thomas Edison and automaker Henry Ford. The estates of both iconic innovators and have been transformed into 20 acres of historical buildings, botanical gardens, research laboratories, and museum exhibits. Get a little history lesson in between trips to the beach.

    Questions we hear the most

    The average flight time from Chicago (Midway) to Fort Myers/Naples is 2 hours 40 minutes.
    There are 147 weekly flights from Chicago (Midway) to Fort Myers/Naples on Southwest Airlines.
    Yes, Southwest flies nonstop from Chicago (Midway) to Fort Myers/Naples 2 times per day from Monday through Friday.
    Yes, Southwest flies nonstop from Chicago (Midway) to Fort Myers/Naples 3 times per day on Saturdays and Sundays.
    To find the lowest fares by day and time to fly Chicago (Midway) to Fort Myers/Naples with Southwest, check out our Low Fare Calendar.
    You can rent a car at Southwest Florida Regional Airport book yours with your flight.
    Yes! Flights from Chicago (Midway) to Fort Myers/Naples—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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