Southwest® flights from Chicago-Midway to Orlando from $189

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Low fares from Chicago-Midway to Orlando

$

Chicago-Midway (MDW)to

Orlando (MCO)
Depart: 12/22/2026

One-way

Basic

From
$189
Seen: 22 hrs ago

Chicago-Midway (MDW)to

Orlando (MCO)
Depart: 12/29/2026

One-way

Basic

From
$189
Seen: 22 hrs ago

Chicago-Midway (MDW)to

Orlando (MCO)
Depart: 12/12/2026

One-way

Basic

From
$189
Seen: 19 hrs ago

Chicago-Midway (MDW)to

Orlando (MCO)
Depart: 01/20/2027

One-way

Basic

From
$189
Seen: 19 hrs ago

Chicago-Midway (MDW)to

Orlando (MCO)
Depart: 01/05/2027

One-way

Basic

From
$189
Seen: 16 hrs ago

Chicago-Midway (MDW)to

Orlando (MCO)
Depart: 01/09/2027

One-way

Basic

From
$189
Seen: 16 hrs ago

Low fares from Chicago-Midway to Orlando

$

Chicago-Midway (MDW)to

Orlando (MCO)
Depart: 12/22/2026

One-way

Basic

From
$189
Seen: 22 hrs ago

Chicago-Midway (MDW)to

Orlando (MCO)
Depart: 12/29/2026

One-way

Basic

From
$189
Seen: 22 hrs ago

Chicago-Midway (MDW)to

Orlando (MCO)
Depart: 12/12/2026

One-way

Basic

From
$189
Seen: 19 hrs ago

Chicago-Midway (MDW)to

Orlando (MCO)
Depart: 01/20/2027

One-way

Basic

From
$189
Seen: 19 hrs ago

Chicago-Midway (MDW)to

Orlando (MCO)
Depart: 01/05/2027

One-way

Basic

From
$189
Seen: 16 hrs ago

Chicago-Midway (MDW)to

Orlando (MCO)
Depart: 01/09/2027

One-way

Basic

From
$189
Seen: 16 hrs ago
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Explore flights from Chicago-Midway to Orlando

cmp-daily-histogram-bars-legend-min-price-aria-label $194
Displaying fares for November-2026
  • MDW–MCO, 11/12/2026: From $199
    12

    Thu

    NOV

  • MDW–MCO, 11/13/2026: From $194
    13

    Fri

  • MDW–MCO, 11/14/2026: From $194
    14

    Sat

  • MDW–MCO, 11/15/2026: From $194
    15

    Sun

  • MDW–MCO, 11/16/2026: From $194
    16

    Mon

  • MDW–MCO, 11/17/2026: From $194
    17

    Tue

  • MDW–MCO, 11/18/2026: From $194
    18

    Wed

  • MDW–MCO, 11/19/2026: From $204
    19

    Thu

  • MDW–MCO, 11/20/2026: From $204
    20

    Fri

  • MDW–MCO, 11/21/2026: From $204
    21

    Sat

  • MDW–MCO, 11/22/2026: From $194
    22

    Sun

  • MDW–MCO, 11/23/2026: From $194
    23

    Mon

  • MDW–MCO, 11/24/2026: From $204
    24

    Tue

  • MDW–MCO, 11/25/2026: From $194
    25

    Wed

  • MDW–MCO, 11/26/2026: From $194
    26

    Thu

  • MDW–MCO, 11/27/2026: From $194
    27

    Fri

  • MDW–MCO, 11/28/2026: From $194
    28

    Sat

  • MDW–MCO, 11/29/2026: From $194
    29

    Sun

  • MDW–MCO, 11/30/2026: From $194
    30

    Mon

  • MDW–MCO, 12/01/2026: From $199
    01

    Tue

    DEC

  • MDW–MCO, 12/02/2026: From $194
    02

    Wed

  • MDW–MCO, 12/03/2026: From $204
    03

    Thu

  • MDW–MCO, 12/04/2026: From $204
    04

    Fri

  • MDW–MCO, 12/05/2026: From $194
    05

    Sat

  • MDW–MCO, 12/06/2026: From $194
    06

    Sun

  • MDW–MCO, 12/07/2026: From $194
    07

    Mon

  • MDW–MCO, 12/08/2026: From $194
    08

    Tue

  • MDW–MCO, 12/09/2026: From $194
    09

    Wed

  • MDW–MCO, 12/10/2026: From $194
    10

    Thu

  • MDW–MCO, 12/11/2026: From $194
    11

    Fri

  • Range$194-$204

    Flight Details

    Departing from:
    Chicago Midway International Airport
    Arriving at:
    Orlando International Airport
    Average flight time:
    2 hours 31 minutes
    Distance:
    990 miles

    Explore Orlando

    Whether you’re visiting Orlando for business, pleasure, or a mix of both, Orlando offers a unique experience for every traveler. Located in Central Florida, expect a welcome as warm as the weather when you meet the locals. But friendly Floridians aren’t the city’s only inhabitants. A robust range of wildlife thrives in the area’s humid subtropical climate, including alligators, snakes, and armadillos. Orlando’s other claim to fame: theme parks. With more than a dozen parks to choose from, Orlando is a hot spot for ride and game lovers across the world. And if you’re looking for a bite to eat, Orlando won’t disappoint. The city’s booming restaurant scene offers delicious cuisine and dining options that range from formal to casual.

    Take a trip to see Orlando’s top sites. As far as attractions go, start by visiting the Kennedy Space Center. Just a hop, skip, and jump from Orlando, Florida’s space getaway is a stop worth making. Even if you don’t catch a rocket launch that day, learning about NASA’s revolutionary journey in space exploration is enough to take you to the stars. And once you’ve worked the left side of your brain, work the right side. The Orlando Museum of Art features several exceptional collections that will arrest your attention from the moment you walk in until the moment you leave.

    Questions we hear the most

    The average flight time from Chicago (Midway) to Orlando is 2 hours 31 minutes.
    There are 156 weekly flights from Chicago (Midway) to Orlando on Southwest Airlines.
    Yes, Southwest flies nonstop from Chicago (Midway) to Orlando 6 times per day from Monday through Friday.
    Yes, Southwest flies nonstop from Chicago (Midway) to Orlando 8 times per day on Saturdays and Sundays.
    To find the lowest fares by day and time to fly Chicago (Midway) to Orlando with Southwest, check out our Low Fare Calendar.
    You can rent a car at Orlando International Airport book yours with your flight.
    Yes! Flights from Chicago (Midway) to Orlando—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.

    Popular Flights from Chicago-Midway