Southwest® flights from Fort Myers/Naples to Chicago (O'Hare)

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Low fares from Fort Myers/Naples to Chicago (O'Hare)

$

Fort Myers/Naples (RSW)to

Chicago (Midway) (MDW)
Depart: 09/19/2026

One-way

Basic

From
$153
Seen: 13 hrs ago

Fort Myers/Naples (RSW)to

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

One-way

Basic

From
$153
Seen: 9 hrs ago

Fort Myers/Naples (RSW)to

Chicago (Midway) (MDW)
Depart: 10/24/2026

One-way

Basic

From
$153
Seen: 10 hrs ago

Fort Myers/Naples (RSW)to

Chicago (Midway) (MDW)
Depart: 09/24/2026

One-way

Basic

From
$153
Seen: 10 hrs ago

Fort Myers/Naples (RSW)to

Chicago (Midway) (MDW)
Depart: 09/10/2026

One-way

Basic

From
$153
Seen: 10 hrs ago

Fort Myers/Naples (RSW)to

Chicago (Midway) (MDW)
Depart: 09/17/2026

One-way

Basic

From
$153
Seen: 8 hrs ago

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Explore flights from Fort Myers/Naples to Chicago (O'Hare)

Aug 2026
From$160*
Seen: 11 hrs ago
One Way/Basic
Sep 2026
From$153*
Seen: 10 hrs ago
One Way/Basic
Oct 2026
From$153*
Seen: 8 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $153
cmp-daily-histogram-bars-legend-max-price-aria-label $263
Displaying fares for August-2026
  • RSW–MDW, 08/05/2026: From $215
    05

    Wed

    AUG

  • 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 $263
    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, 08/16/2026: From $263
    16

    Sun

  • RSW–MDW, 08/17/2026: From $253
    17

    Mon

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

    Tue

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

    Wed

  • RSW–MDW, 08/20/2026: From $253
    20

    Thu

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

    Fri

  • RSW–MDW, 08/22/2026: From $215
    22

    Sat

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

    Sun

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

    Mon

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

    Tue

  • RSW–MDW: cmp-view-offers-disclaimer. Find Offers
    26

    Wed

  • RSW–MDW: cmp-view-offers-disclaimer. Find Offers
    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 $250
    30

    Sun

  • RSW–MDW, 08/31/2026: From $160
    31

    Mon

  • RSW–MDW: cmp-view-offers-disclaimer. Find Offers
    01

    Tue

    SEP

  • RSW–MDW: cmp-view-offers-disclaimer. Find Offers
    02

    Wed

  • RSW–MDW, 09/03/2026: From $153
    03

    Thu

  • RSW–MDW, 09/04/2026: From $172
    04

    Fri

    • Range$153-$263

    *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:
    O'Hare International Airport
    Distance:
    1120 miles

    Route Information

    41† Weekly flights

    † 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

    There are 41 weekly flights from Fort Myers/Naples to Chicago (O'Hare) on Southwest Airlines.
    To find the lowest fares by day and time to fly Fort Myers/Naples to Chicago (O'Hare) with Southwest, check out our Low Fare Calendar.
    You can rent a car at O'Hare International Airport book yours with your flight.
    Yes! Flights from Fort Myers/Naples to Chicago (O'Hare)—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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