Southwest® flights from Tampa to Chicago-Midway from $96

Promo Code

Low fares from Tampa to Chicago-Midway

$

Tampa (TPA)to

Chicago-Midway (MDW)
Depart: 01/23/2027

One-way

Basic

From
$96
Seen: 12 hrs ago

Tampa (TPA)to

Chicago-Midway (MDW)
Depart: 11/10/2026

One-way

Basic

From
$96
Seen: 20 hrs ago

Tampa (TPA)to

Chicago-Midway (MDW)
Depart: 01/16/2027

One-way

Basic

From
$96
Seen: 6 hrs ago

Tampa (TPA)to

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

One-way

Basic

From
$96
Seen: 5 hrs ago

Tampa (TPA)to

Chicago-Midway (MDW)
Depart: 12/05/2026

One-way

Basic

From
$96
Seen: 21 minutes ago

Tampa (TPA)to

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

One-way

Basic

From
$96
Seen: 19 hrs ago

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Explore flights from Tampa to Chicago-Midway

Oct 2026
From$207*
Seen: 2 hrs ago
One Way/Basic
Nov 2026
From$96*
Seen: 20 hrs ago
One Way/Basic
Dec 2026
From$96*
Seen: 23 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $96
cmp-daily-histogram-bars-legend-max-price-aria-label $256
Displaying fares for October-2026
  • TPA–MDW, 10/22/2026: From $246
    22

    Thu

    OCT

  • TPA–MDW, 10/23/2026: From $246
    23

    Fri

  • TPA–MDW, 10/24/2026: From $207
    24

    Sat

  • TPA–MDW, 10/25/2026: From $256
    25

    Sun

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

    Mon

  • TPA–MDW, 10/27/2026: From $212
    27

    Tue

  • TPA–MDW, 10/28/2026: From $212
    28

    Wed

  • TPA–MDW, 10/29/2026: From $246
    29

    Thu

  • TPA–MDW, 10/30/2026: From $246
    30

    Fri

  • TPA–MDW: cmp-view-offers-disclaimer. Find Offers
    31

    Sat

  • TPA–MDW, 11/01/2026: From $246
    01

    Sun

    NOV

  • TPA–MDW, 11/02/2026: From $246
    02

    Mon

  • TPA–MDW, 11/03/2026: From $207
    03

    Tue

  • TPA–MDW, 11/04/2026: From $207
    04

    Wed

  • TPA–MDW, 11/05/2026: From $246
    05

    Thu

  • TPA–MDW, 11/06/2026: From $246
    06

    Fri

  • TPA–MDW, 11/07/2026: From $207
    07

    Sat

  • TPA–MDW: cmp-view-offers-disclaimer. Find Offers
    08

    Sun

  • TPA–MDW, 11/09/2026: From $127
    09

    Mon

  • TPA–MDW, 11/10/2026: From $96
    10

    Tue

  • TPA–MDW, 11/11/2026: From $96
    11

    Wed

  • TPA–MDW, 11/12/2026: From $102
    12

    Thu

  • TPA–MDW, 11/13/2026: From $122
    13

    Fri

  • TPA–MDW, 11/14/2026: From $106
    14

    Sat

  • TPA–MDW, 11/15/2026: From $132
    15

    Sun

  • TPA–MDW, 11/16/2026: From $242
    16

    Mon

  • TPA–MDW: cmp-view-offers-disclaimer. Find Offers
    17

    Tue

  • TPA–MDW, 11/18/2026: From $96
    18

    Wed

  • TPA–MDW, 11/19/2026: From $97
    19

    Thu

  • TPA–MDW, 11/20/2026: From $206
    20

    Fri

  • TPA–MDW, 11/21/2026: From $106
    21

    Sat

    • Range$96-$256

    *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:
    Tampa International Airport
    Arriving at:
    Chicago Midway International Airport
    Average flight time:
    2 hours 38 minutes
    Distance:
    997 miles

    Questions we hear the most

    The average flight time from Tampa to Chicago (Midway) is 2 hours 38 minutes.
    There are 156 weekly flights from Tampa to Chicago (Midway) on Southwest Airlines.
    Yes, Southwest flies nonstop from Tampa to Chicago (Midway) 3 times per day from Monday through Friday.
    Yes, Southwest flies nonstop from Tampa to Chicago (Midway) 3 times per day on Saturdays and 4 times per day on Sundays.
    To find the lowest fares by day and time to fly Tampa 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 Tampa 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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