Southwest® flights from Tampa to Chicago-Midway from $139

Promo Code

Low fares from Tampa to Chicago-Midway

$

Tampa (TPA)to

Chicago-Midway (MDW)
Depart: 11/19/2026

One-way

Basic

From
$139
Seen: 10 hrs ago

Tampa (TPA)to

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

One-way

Basic

From
$139
Seen: 12 hrs ago

Tampa (TPA)to

Chicago-Midway (MDW)
Depart: 10/29/2026

One-way

Basic

From
$139
Seen: 12 hrs ago

Tampa (TPA)to

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

One-way

Basic

From
$139
Seen: 4 hrs ago

Tampa (TPA)to

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

One-way

Basic

From
$139
Seen: 3 hrs ago

Tampa (TPA)to

Chicago-Midway (MDW)
Depart: 11/26/2026

One-way

Basic

From
$139
Seen: 2 hrs ago

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Explore flights from Tampa to Chicago-Midway

Oct 2026
From$139*
Seen: 12 hrs ago
One Way/Basic
Nov 2026
From$139*
Seen: 16 hrs ago
One Way/Basic
Dec 2026
From$139*
Seen: 9 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $139
cmp-daily-histogram-bars-legend-max-price-aria-label $276
Displaying fares for October-2026
  • TPA–MDW, 10/01/2026: From $276
    01

    Thu

    OCT

  • TPA–MDW, 10/02/2026: From $236
    02

    Fri

  • TPA–MDW, 10/03/2026: From $197
    03

    Sat

  • TPA–MDW, 10/04/2026: From $236
    04

    Sun

  • TPA–MDW, 10/05/2026: From $236
    05

    Mon

  • TPA–MDW, 10/06/2026: From $197
    06

    Tue

  • TPA–MDW, 10/07/2026: From $197
    07

    Wed

  • TPA–MDW, 10/08/2026: From $236
    08

    Thu

  • TPA–MDW, 10/09/2026: From $236
    09

    Fri

  • TPA–MDW: cmp-view-offers-disclaimer. Find Offers
    10

    Sat

  • TPA–MDW, 10/11/2026: From $236
    11

    Sun

  • TPA–MDW: cmp-view-offers-disclaimer. Find Offers
    12

    Mon

  • TPA–MDW, 10/13/2026: From $207
    13

    Tue

  • TPA–MDW, 10/14/2026: From $197
    14

    Wed

  • TPA–MDW, 10/15/2026: From $236
    15

    Thu

  • TPA–MDW, 10/16/2026: From $236
    16

    Fri

  • TPA–MDW, 10/17/2026: From $207
    17

    Sat

  • TPA–MDW, 10/18/2026: From $236
    18

    Sun

  • TPA–MDW, 10/19/2026: From $236
    19

    Mon

  • TPA–MDW, 10/20/2026: From $197
    20

    Tue

  • TPA–MDW, 10/21/2026: From $197
    21

    Wed

  • TPA–MDW, 10/22/2026: From $139
    22

    Thu

  • TPA–MDW, 10/23/2026: From $149
    23

    Fri

  • TPA–MDW, 10/24/2026: From $149
    24

    Sat

  • TPA–MDW, 10/25/2026: From $232
    25

    Sun

  • TPA–MDW, 10/26/2026: From $149
    26

    Mon

  • TPA–MDW, 10/27/2026: From $139
    27

    Tue

  • TPA–MDW, 10/28/2026: From $139
    28

    Wed

  • TPA–MDW, 10/29/2026: From $139
    29

    Thu

  • TPA–MDW, 10/30/2026: From $149
    30

    Fri

  • TPA–MDW, 10/31/2026: From $139
    31

    Sat

    • Range$139-$276

    *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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