Southwest® flights from Chicago-Midway to Fort Myers/Naples from $157

Promo Code

Low fares from Chicago-Midway to Fort Myers/Naples

$

Chicago-Midway (MDW)to

Fort Myers/Naples (RSW)
Depart: 12/01/2026

One-way

Basic

From
$157
Seen: 18 hrs ago

Chicago-Midway (MDW)to

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

One-way

Basic

From
$157
Seen: 13 hrs ago

Chicago-Midway (MDW)to

Fort Myers/Naples (RSW)
Depart: 11/02/2026

One-way

Basic

From
$157
Seen: 12 hrs ago

Chicago-Midway (MDW)to

Fort Myers/Naples (RSW)
Depart: 10/27/2026

One-way

Basic

From
$157
Seen: 11 hrs ago

Chicago-Midway (MDW)to

Fort Myers/Naples (RSW)
Depart: 11/03/2026

One-way

Basic

From
$157
Seen: 4 hrs ago

Chicago-Midway (MDW)to

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

One-way

Basic

From
$157
Seen: 6 hrs ago

Looking for more low-fare flights?

Check out the Low Fare Calendar to find a fare that works for you. Just choose the month you want to depart and return, and we’ll show you the best fares available.

Find low fares

Explore flights from Chicago-Midway to Fort Myers/Naples

Oct 2026
From$157*
Seen: 11 hrs ago
One Way/Basic
Nov 2026
From$157*
Seen: 22 hrs ago
One Way/Basic
Dec 2026
From$157*
Seen: 8 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $157
cmp-daily-histogram-bars-legend-max-price-aria-label $283
Displaying fares for October-2026
  • MDW–RSW, 10/02/2026: From $273
    02

    Fri

    OCT

  • MDW–RSW, 10/03/2026: From $225
    03

    Sat

  • MDW–RSW, 10/04/2026: From $273
    04

    Sun

  • MDW–RSW, 10/05/2026: From $273
    05

    Mon

  • MDW–RSW, 10/06/2026: From $225
    06

    Tue

  • MDW–RSW, 10/07/2026: From $225
    07

    Wed

  • MDW–RSW, 10/08/2026: From $283
    08

    Thu

  • MDW–RSW, 10/09/2026: From $283
    09

    Fri

  • MDW–RSW, 10/10/2026: From $225
    10

    Sat

  • MDW–RSW, 10/11/2026: From $273
    11

    Sun

  • MDW–RSW, 10/12/2026: From $273
    12

    Mon

  • MDW–RSW, 10/13/2026: From $235
    13

    Tue

  • MDW–RSW, 10/14/2026: From $225
    14

    Wed

  • MDW–RSW, 10/15/2026: From $273
    15

    Thu

  • MDW–RSW, 10/16/2026: From $273
    16

    Fri

  • MDW–RSW, 10/17/2026: From $270
    17

    Sat

  • MDW–RSW, 10/18/2026: From $273
    18

    Sun

  • MDW–RSW, 10/19/2026: From $273
    19

    Mon

  • MDW–RSW, 10/20/2026: From $225
    20

    Tue

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

    Wed

  • MDW–RSW, 10/22/2026: From $207
    22

    Thu

  • MDW–RSW, 10/23/2026: From $195
    23

    Fri

  • MDW–RSW, 10/24/2026: From $167
    24

    Sat

  • MDW–RSW, 10/25/2026: From $270
    25

    Sun

  • MDW–RSW, 10/26/2026: From $157
    26

    Mon

  • MDW–RSW, 10/27/2026: From $157
    27

    Tue

  • MDW–RSW, 10/28/2026: From $157
    28

    Wed

  • MDW–RSW, 10/29/2026: From $157
    29

    Thu

  • MDW–RSW, 10/30/2026: From $180
    30

    Fri

  • MDW–RSW, 10/31/2026: From $172
    31

    Sat

  • MDW–RSW, 11/01/2026: From $204
    01

    Sun

    NOV

    • Range$157-$283

    *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

    Route Information

    147† 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.

    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.

    Explore Flights from Other Popular Origins

    Popular Flights from Chicago-Midway