Southwest® flights from Tampa to Chicago-Midway from $156

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Low fares from Tampa to Chicago-Midway

$

Tampa (TPA)to

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

One-way

Basic

From
$156
Seen: 7 hrs ago

Tampa (TPA)to

Chicago-Midway (MDW)
Depart: 01/26/2027

One-way

Basic

From
$156
Seen: 1 hour ago

Tampa (TPA)to

Chicago-Midway (MDW)
Depart: 02/03/2027

One-way

Basic

From
$156
Seen: 2 hrs ago

Tampa (TPA)to

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

One-way

Basic

From
$156
Seen: 1 hour ago

Tampa (TPA)to

Chicago-Midway (MDW)
Depart: 02/17/2027

One-way

Basic

From
$156
Seen: 15 hrs ago

Tampa (TPA)to

Chicago-Midway (MDW)
Depart: 01/09/2027

One-way

Basic

From
$156
Seen: 16 hrs ago

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Explore flights from Tampa to Chicago-Midway

Nov 2026
From$212*
Seen: 1 hour ago
One Way/Basic
Dec 2026
From$156*
Seen: 2 hrs ago
One Way/Basic
Jan 2027
From$156*
Seen: 18 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $171
cmp-daily-histogram-bars-legend-max-price-aria-label $450
Displaying fares for November-2026
  • TPA–MDW, 11/11/2026: From $212
    11

    Wed

    NOV

  • TPA–MDW, 11/12/2026: From $251
    12

    Thu

  • TPA–MDW, 11/13/2026: From $251
    13

    Fri

  • TPA–MDW, 11/14/2026: From $212
    14

    Sat

  • TPA–MDW, 11/15/2026: From $340
    15

    Sun

  • TPA–MDW, 11/16/2026: From $261
    16

    Mon

  • TPA–MDW, 11/17/2026: From $212
    17

    Tue

  • TPA–MDW, 11/18/2026: From $212
    18

    Wed

  • TPA–MDW, 11/19/2026: From $251
    19

    Thu

  • TPA–MDW, 11/20/2026: From $251
    20

    Fri

  • TPA–MDW, 11/21/2026: From $212
    21

    Sat

  • TPA–MDW, 11/22/2026: From $251
    22

    Sun

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

    Mon

  • TPA–MDW, 11/24/2026: From $212
    24

    Tue

  • TPA–MDW, 11/25/2026: From $212
    25

    Wed

  • TPA–MDW, 11/26/2026: From $251
    26

    Thu

  • TPA–MDW, 11/27/2026: From $261
    27

    Fri

  • TPA–MDW, 11/28/2026: From $340
    28

    Sat

  • TPA–MDW, 11/29/2026: From $450
    29

    Sun

  • TPA–MDW, 11/30/2026: From $261
    30

    Mon

  • TPA–MDW, 12/01/2026: From $177
    01

    Tue

    DEC

  • TPA–MDW, 12/02/2026: From $172
    02

    Wed

  • TPA–MDW: cmp-view-offers-disclaimer. Find Offers
    03

    Thu

  • TPA–MDW, 12/04/2026: From $207
    04

    Fri

  • TPA–MDW, 12/05/2026: From $172
    05

    Sat

  • TPA–MDW, 12/06/2026: From $247
    06

    Sun

  • TPA–MDW, 12/07/2026: From $182
    07

    Mon

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

    Tue

  • TPA–MDW, 12/09/2026: From $172
    09

    Wed

  • TPA–MDW, 12/10/2026: From $171
    10

    Thu

    • Range$171-$450

    *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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