Southwest® flights from Tampa to Chicago (Midway) from $105

Promo Code

Low fares from Tampa to Chicago (Midway)

$

Tampa (TPA)to

Chicago (Midway) (MDW)
Depart: 11/02/2026

One-way

Basic

From
$105
Seen: 22 hrs ago

Tampa (TPA)to

Chicago (Midway) (MDW)
Depart: 11/03/2026

One-way

Basic

From
$105
Seen: 18 hrs ago

Tampa (TPA)to

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

One-way

Basic

From
$105
Seen: 20 hrs ago

Tampa (TPA)to

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

One-way

Basic

From
$105
Seen: 9 hrs ago

Tampa (TPA)to

Chicago (Midway) (MDW)
Depart: 10/06/2026

One-way

Basic

From
$105
Seen: 14 hrs ago

Tampa (TPA)to

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

One-way

Basic

From
$105
Seen: 14 hrs ago

Looking for more low-fare flights?

Check out the Low Fare Calendar to find a fare that works for you. Just choose the month you want to depart and return, and we’ll show you the best fares available.

Find low fares

Explore flights from Tampa to Chicago (Midway)

Aug 2026
From$177*
Seen: 15 hrs ago
One Way/Basic
Sep 2026
From$105*
Seen: 9 hrs ago
One Way/Basic
Oct 2026
From$105*
Seen: 22 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $105
cmp-daily-histogram-bars-legend-max-price-aria-label $226
Displaying fares for August-2026
  • TPA–MDW, 08/23/2026: From $226
    23

    Sun

    AUG

  • TPA–MDW, 08/24/2026: From $216
    24

    Mon

  • TPA–MDW, 08/25/2026: From $177
    25

    Tue

  • TPA–MDW, 08/26/2026: From $177
    26

    Wed

  • TPA–MDW, 08/27/2026: From $226
    27

    Thu

  • TPA–MDW, 08/28/2026: From $216
    28

    Fri

  • TPA–MDW, 08/29/2026: From $177
    29

    Sat

  • TPA–MDW, 08/30/2026: From $216
    30

    Sun

  • TPA–MDW, 08/31/2026: From $216
    31

    Mon

  • TPA–MDW, 09/01/2026: From $177
    01

    Tue

    SEP

  • TPA–MDW, 09/02/2026: From $177
    02

    Wed

  • TPA–MDW, 09/03/2026: From $216
    03

    Thu

  • TPA–MDW, 09/04/2026: From $226
    04

    Fri

  • TPA–MDW, 09/05/2026: From $131
    05

    Sat

  • TPA–MDW, 09/06/2026: From $121
    06

    Sun

  • TPA–MDW, 09/07/2026: From $226
    07

    Mon

  • TPA–MDW, 09/08/2026: From $187
    08

    Tue

  • TPA–MDW, 09/09/2026: From $131
    09

    Wed

  • TPA–MDW, 09/10/2026: From $121
    10

    Thu

  • TPA–MDW, 09/11/2026: From $121
    11

    Fri

  • TPA–MDW, 09/12/2026: From $110
    12

    Sat

  • TPA–MDW, 09/13/2026: From $212
    13

    Sun

  • TPA–MDW, 09/14/2026: From $155
    14

    Mon

  • TPA–MDW, 09/15/2026: From $105
    15

    Tue

  • TPA–MDW: cmp-view-offers-disclaimer. Find Offers
    16

    Wed

  • TPA–MDW, 09/17/2026: From $155
    17

    Thu

  • TPA–MDW, 09/18/2026: From $118
    18

    Fri

  • TPA–MDW, 09/19/2026: From $105
    19

    Sat

  • TPA–MDW: cmp-view-offers-disclaimer. Find Offers
    20

    Sun

  • TPA–MDW, 09/21/2026: From $165
    21

    Mon

  • TPA–MDW, 09/22/2026: From $115
    22

    Tue

    • Range$105-$226

    *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.

    Explore Flights from Other Popular Origins

    Popular Flights from Tampa