Southwest® flights from Fort Myers/Naples to Chicago-Midway from $141

Promo Code

Low fares from Fort Myers/Naples to Chicago-Midway

$

Fort Myers/Naples (RSW)to

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

One-way

Basic

From
$141
Seen: 1 hour ago

Fort Myers/Naples (RSW)to

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

One-way

Basic

From
$173
Seen: 19 hrs ago

Fort Myers/Naples (RSW)to

Chicago-Midway (MDW)
Depart: 12/30/2026

One-way

Basic

From
$173
Seen: 5 hrs ago

Fort Myers/Naples (RSW)to

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

One-way

Basic

From
$173
Seen: 19 hrs ago

Fort Myers/Naples (RSW)to

Chicago-Midway (MDW)
Depart: 12/22/2026

One-way

Basic

From
$173
Seen: 20 hrs ago

Fort Myers/Naples (RSW)to

Chicago-Midway (MDW)
Depart: 12/15/2026

One-way

Basic

From
$173
Seen: 20 hrs ago

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Explore flights from Fort Myers/Naples to Chicago-Midway

Nov 2026
From$222*
Seen: 17 hrs ago
One Way/Basic
Dec 2026
From$141*
Seen: 1 hour ago
One Way/Basic
Jan 2027
From$173*
Seen: 18 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $173
cmp-daily-histogram-bars-legend-max-price-aria-label $456
Displaying fares for November-2026
  • RSW–MDW, 11/11/2026: From $222
    11

    Wed

    NOV

  • RSW–MDW, 11/12/2026: From $222
    12

    Thu

  • RSW–MDW, 11/13/2026: From $222
    13

    Fri

  • RSW–MDW, 11/14/2026: From $222
    14

    Sat

  • RSW–MDW, 11/15/2026: From $254
    15

    Sun

  • RSW–MDW, 11/16/2026: From $232
    16

    Mon

  • RSW–MDW, 11/17/2026: From $222
    17

    Tue

  • RSW–MDW, 11/18/2026: From $222
    18

    Wed

  • RSW–MDW, 11/19/2026: From $222
    19

    Thu

  • RSW–MDW, 11/20/2026: From $222
    20

    Fri

  • RSW–MDW, 11/21/2026: From $227
    21

    Sat

  • RSW–MDW, 11/22/2026: From $222
    22

    Sun

  • RSW–MDW, 11/23/2026: From $222
    23

    Mon

  • RSW–MDW, 11/24/2026: From $222
    24

    Tue

  • RSW–MDW, 11/25/2026: From $222
    25

    Wed

  • RSW–MDW, 11/26/2026: From $222
    26

    Thu

  • RSW–MDW, 11/27/2026: From $264
    27

    Fri

  • RSW–MDW, 11/28/2026: From $456
    28

    Sat

  • RSW–MDW: cmp-view-offers-disclaimer. Find Offers
    29

    Sun

  • RSW–MDW, 11/30/2026: From $319
    30

    Mon

  • RSW–MDW, 12/01/2026: From $232
    01

    Tue

    DEC

  • RSW–MDW, 12/02/2026: From $173
    02

    Wed

  • RSW–MDW, 12/03/2026: From $193
    03

    Thu

  • RSW–MDW, 12/04/2026: From $208
    04

    Fri

  • RSW–MDW, 12/05/2026: From $173
    05

    Sat

  • RSW–MDW, 12/06/2026: From $222
    06

    Sun

  • RSW–MDW, 12/07/2026: From $193
    07

    Mon

  • RSW–MDW, 12/08/2026: From $173
    08

    Tue

  • RSW–MDW, 12/09/2026: From $173
    09

    Wed

  • RSW–MDW, 12/10/2026: From $193
    10

    Thu

    • Range$173-$456

    *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

    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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