Southwest® flights from Fort Myers/Naples to Chicago-Midway from $149

Promo Code

Low fares from Fort Myers/Naples to Chicago-Midway

$

Fort Myers/Naples (RSW)to

Chicago-Midway (MDW)
Depart: 12/08/2026

One-way

Basic

From
$149
Seen: 12 hrs ago

Fort Myers/Naples (RSW)to

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

One-way

Basic

From
$149
Seen: 14 hrs ago

Fort Myers/Naples (RSW)to

Chicago-Midway (MDW)
Depart: 10/01/2026

One-way

Basic

From
$149
Seen: 9 hrs ago

Fort Myers/Naples (RSW)to

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

One-way

Basic

From
$149
Seen: 17 hrs ago

Fort Myers/Naples (RSW)to

Chicago-Midway (MDW)
Depart: 12/17/2026

One-way

Basic

From
$149
Seen: 15 hrs ago

Fort Myers/Naples (RSW)to

Chicago-Midway (MDW)
Depart: 12/09/2026

One-way

Basic

From
$149
Seen: 11 hrs ago

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Explore flights from Fort Myers/Naples to Chicago-Midway

Sep 2026
From$215*
Seen: 17 hrs ago
One Way/Basic
Oct 2026
From$149*
Seen: 17 hrs ago
One Way/Basic
Nov 2026
From$149*
Seen: 10 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $149
cmp-daily-histogram-bars-legend-max-price-aria-label $273
Displaying fares for September-2026
  • RSW–MDW, 09/11/2026: From $273
    11

    Fri

    SEP

  • RSW–MDW, 09/12/2026: From $235
    12

    Sat

  • RSW–MDW, 09/13/2026: From $273
    13

    Sun

  • RSW–MDW, 09/14/2026: From $273
    14

    Mon

  • RSW–MDW, 09/15/2026: From $225
    15

    Tue

  • RSW–MDW, 09/16/2026: From $225
    16

    Wed

  • RSW–MDW, 09/17/2026: From $273
    17

    Thu

  • RSW–MDW, 09/18/2026: From $273
    18

    Fri

  • RSW–MDW, 09/19/2026: From $215
    19

    Sat

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

    Sun

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

    Mon

  • RSW–MDW, 09/22/2026: From $225
    22

    Tue

  • RSW–MDW, 09/23/2026: From $225
    23

    Wed

  • RSW–MDW, 09/24/2026: From $273
    24

    Thu

  • RSW–MDW, 09/25/2026: From $273
    25

    Fri

  • RSW–MDW, 09/26/2026: From $225
    26

    Sat

  • RSW–MDW, 09/27/2026: From $273
    27

    Sun

  • RSW–MDW, 09/28/2026: From $273
    28

    Mon

  • RSW–MDW, 09/29/2026: From $215
    29

    Tue

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

    Wed

  • RSW–MDW, 10/01/2026: From $149
    01

    Thu

    OCT

  • RSW–MDW, 10/02/2026: From $170
    02

    Fri

  • RSW–MDW, 10/03/2026: From $149
    03

    Sat

  • RSW–MDW, 10/04/2026: From $270
    04

    Sun

  • RSW–MDW, 10/05/2026: From $182
    05

    Mon

  • RSW–MDW, 10/06/2026: From $182
    06

    Tue

  • RSW–MDW, 10/07/2026: From $182
    07

    Wed

  • RSW–MDW, 10/08/2026: From $182
    08

    Thu

  • RSW–MDW, 10/09/2026: From $182
    09

    Fri

  • RSW–MDW, 10/10/2026: From $182
    10

    Sat

    • Range$149-$273

    *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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