Southwest® flights from Tucson to Chicago-Midway from $199

Promo Code

Low fares from Tucson to Chicago-Midway

$

Tucson (TUS)to

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

One-way

Basic

From
$199
Seen: 1 hour ago

Tucson (TUS)to

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

One-way

Basic

From
$199
Seen: 1 hour ago

Tucson (TUS)to

Chicago-Midway (MDW)
Depart: 12/03/2026

One-way

Basic

From
$199
Seen: 17 minutes ago

Tucson (TUS)to

Chicago-Midway (MDW)
Depart: 10/28/2026

One-way

Basic

From
$199
Seen: 16 hrs ago

Tucson (TUS)to

Chicago-Midway (MDW)
Depart: 01/07/2027

One-way

Basic

From
$199
Seen: 19 hrs ago

Tucson (TUS)to

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

One-way

Basic

From
$199
Seen: 8 hrs ago

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Explore flights from Tucson to Chicago-Midway

Oct 2026
From$199*
Seen: 1 hour ago
One Way/Basic
Nov 2026
From$199*
Seen: 8 hrs ago
One Way/Basic
Dec 2026
From$199*
Seen: 1 hour ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $199
cmp-daily-histogram-bars-legend-max-price-aria-label $306
Displaying fares for October-2026
  • TUS–MDW, 10/02/2026: From $300
    02

    Fri

    OCT

  • TUS–MDW, 10/03/2026: From $268
    03

    Sat

  • TUS–MDW: cmp-view-offers-disclaimer. Find Offers
    04

    Sun

  • TUS–MDW, 10/05/2026: From $306
    05

    Mon

  • TUS–MDW, 10/06/2026: From $268
    06

    Tue

  • TUS–MDW, 10/07/2026: From $258
    07

    Wed

  • TUS–MDW, 10/08/2026: From $306
    08

    Thu

  • TUS–MDW, 10/09/2026: From $306
    09

    Fri

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

    Sat

  • TUS–MDW, 10/11/2026: From $296
    11

    Sun

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

    Mon

  • TUS–MDW: cmp-view-offers-disclaimer. Find Offers
    13

    Tue

  • TUS–MDW, 10/14/2026: From $258
    14

    Wed

  • TUS–MDW: cmp-view-offers-disclaimer. Find Offers
    15

    Thu

  • TUS–MDW, 10/16/2026: From $296
    16

    Fri

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

    Sat

  • TUS–MDW, 10/18/2026: From $296
    18

    Sun

  • TUS–MDW: cmp-view-offers-disclaimer. Find Offers
    19

    Mon

  • TUS–MDW, 10/20/2026: From $258
    20

    Tue

  • TUS–MDW, 10/21/2026: From $258
    21

    Wed

  • TUS–MDW: cmp-view-offers-disclaimer. Find Offers
    22

    Thu

  • TUS–MDW, 10/23/2026: From $222
    23

    Fri

  • TUS–MDW: cmp-view-offers-disclaimer. Find Offers
    24

    Sat

  • TUS–MDW, 10/25/2026: From $302
    25

    Sun

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

    Mon

  • TUS–MDW, 10/27/2026: From $199
    27

    Tue

  • TUS–MDW, 10/28/2026: From $199
    28

    Wed

  • TUS–MDW: cmp-view-offers-disclaimer. Find Offers
    29

    Thu

  • TUS–MDW, 10/30/2026: From $222
    30

    Fri

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

    Sat

  • TUS–MDW, 11/01/2026: From $261
    01

    Sun

    NOV

    • Range$199-$306

    *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:
    Tucson International Airport
    Arriving at:
    Chicago Midway International Airport
    Average flight time:
    3 hours 22 minutes
    Distance:
    1440 miles

    Route Information

    144† Weekly flights
    • 1‡ Nonstop flight per day Monday through Friday
    • 1‡ Nonstop flight on Saturday
    • 1‡ Nonstop flight 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 Tucson to Chicago (Midway) is 3 hours 22 minutes.
    There are 144 weekly flights from Tucson to Chicago (Midway) on Southwest Airlines.
    Yes, Southwest flies nonstop from Tucson to Chicago (Midway) once per day from Monday through Friday.
    Yes, Southwest flies nonstop from Tucson to Chicago (Midway) once per day on Saturdays and Sundays.
    To find the lowest fares by day and time to fly Tucson 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 Tucson 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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