Southwest® flights from Tampa to Chicago-Midway from $131

Promo Code

Low fares from Tampa to Chicago-Midway

$

Tampa (TPA)to

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

One-way

Basic

From
$131
Seen: 11 hrs ago

Tampa (TPA)to

Chicago-Midway (MDW)
Depart: 10/27/2026

One-way

Basic

From
$131
Seen: 11 hrs ago

Tampa (TPA)to

Chicago-Midway (MDW)
Depart: 10/14/2026

One-way

Basic

From
$131
Seen: 12 hrs ago

Tampa (TPA)to

Chicago-Midway (MDW)
Depart: 11/18/2026

One-way

Basic

From
$131
Seen: 11 hrs ago

Tampa (TPA)to

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

One-way

Basic

From
$131
Seen: 6 hrs ago

Tampa (TPA)to

Chicago-Midway (MDW)
Depart: 12/16/2026

One-way

Basic

From
$131
Seen: 6 hrs ago

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Explore flights from Tampa to Chicago-Midway

Sep 2026
From$197*
Seen: 16 hrs ago
One Way/Basic
Oct 2026
From$131*
Seen: 12 hrs ago
One Way/Basic
Nov 2026
From$131*
Seen: 11 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $182
cmp-daily-histogram-bars-legend-max-price-aria-label $263
Displaying fares for September-2026
  • TPA–MDW, 09/11/2026: From $246
    11

    Fri

    SEP

  • TPA–MDW, 09/12/2026: From $197
    12

    Sat

  • TPA–MDW, 09/13/2026: From $263
    13

    Sun

  • TPA–MDW, 09/14/2026: From $246
    14

    Mon

  • TPA–MDW, 09/15/2026: From $197
    15

    Tue

  • TPA–MDW, 09/16/2026: From $207
    16

    Wed

  • TPA–MDW, 09/17/2026: From $236
    17

    Thu

  • TPA–MDW, 09/18/2026: From $236
    18

    Fri

  • TPA–MDW, 09/19/2026: From $197
    19

    Sat

  • TPA–MDW, 09/20/2026: From $236
    20

    Sun

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

    Mon

  • TPA–MDW, 09/22/2026: From $207
    22

    Tue

  • TPA–MDW, 09/23/2026: From $197
    23

    Wed

  • TPA–MDW, 09/24/2026: From $236
    24

    Thu

  • TPA–MDW, 09/25/2026: From $236
    25

    Fri

  • TPA–MDW, 09/26/2026: From $197
    26

    Sat

  • TPA–MDW, 09/27/2026: From $236
    27

    Sun

  • TPA–MDW, 09/28/2026: From $236
    28

    Mon

  • TPA–MDW, 09/29/2026: From $197
    29

    Tue

  • TPA–MDW, 09/30/2026: From $197
    30

    Wed

  • TPA–MDW, 10/01/2026: From $236
    01

    Thu

    OCT

  • TPA–MDW, 10/02/2026: From $182
    02

    Fri

  • TPA–MDW, 10/03/2026: From $182
    03

    Sat

  • TPA–MDW, 10/04/2026: From $232
    04

    Sun

  • TPA–MDW, 10/05/2026: From $192
    05

    Mon

  • TPA–MDW, 10/06/2026: From $182
    06

    Tue

  • TPA–MDW, 10/07/2026: From $182
    07

    Wed

  • TPA–MDW, 10/08/2026: From $182
    08

    Thu

  • TPA–MDW, 10/09/2026: From $182
    09

    Fri

  • TPA–MDW, 10/10/2026: From $182
    10

    Sat

    • Range$182-$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:
    Tampa International Airport
    Arriving at:
    Chicago Midway International Airport
    Average flight time:
    2 hours 38 minutes
    Distance:
    997 miles

    Route Information

    156† Weekly flights
    • 3‡ Nonstop flights per day Monday through Friday
    • 3‡ Nonstop flights on Saturday
    • 4‡ 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.

    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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