Southwest® flights from Tucson to Chicago (Midway) from $169

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Low fares from Tucson to Chicago (Midway)

$

Tucson (TUS)to

Chicago (Midway) (MDW)
Depart: 10/21/2026

One-way

Basic

From
$169
Seen: 3 hrs ago

Tucson (TUS)to

Chicago (Midway) (MDW)
Depart: 10/12/2026

One-way

Basic

From
$169
Seen: 3 hrs ago

Tucson (TUS)to

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

One-way

Basic

From
$169
Seen: 8 hrs ago

Tucson (TUS)to

Chicago (Midway) (MDW)
Depart: 11/04/2026

One-way

Basic

From
$169
Seen: 4 hrs ago

Tucson (TUS)to

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

One-way

Basic

From
$169
Seen: 15 hrs ago

Tucson (TUS)to

Chicago (Midway) (MDW)
Depart: 09/19/2026

One-way

Basic

From
$179
Seen: 12 hrs ago

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Explore flights from Tucson to Chicago (Midway)

Aug 2026
From$248*
Seen: 23 hrs ago
One Way/Basic
Sep 2026
From$179*
Seen: 19 hrs ago
One Way/Basic
Oct 2026
From$169*
Seen: 8 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $179
cmp-daily-histogram-bars-legend-max-price-aria-label $286
Displaying fares for August-2026
  • TUS–MDW, 08/22/2026: From $248
    22

    Sat

    AUG

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

    Sun

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    24

    Mon

  • TUS–MDW, 08/25/2026: From $248
    25

    Tue

  • TUS–MDW, 08/26/2026: From $248
    26

    Wed

  • TUS–MDW, 08/27/2026: From $286
    27

    Thu

  • TUS–MDW, 08/28/2026: From $286
    28

    Fri

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    29

    Sat

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    30

    Sun

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    31

    Mon

  • TUS–MDW: cmp-view-offers-disclaimer. Find Offers
    01

    Tue

    SEP

  • TUS–MDW, 09/02/2026: From $248
    02

    Wed

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    03

    Thu

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    04

    Fri

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    05

    Sat

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    06

    Sun

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    07

    Mon

  • TUS–MDW, 09/08/2026: From $248
    08

    Tue

  • TUS–MDW, 09/09/2026: From $219
    09

    Wed

  • TUS–MDW, 09/10/2026: From $219
    10

    Thu

  • TUS–MDW: cmp-view-offers-disclaimer. Find Offers
    11

    Fri

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    12

    Sat

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    13

    Sun

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    14

    Mon

  • TUS–MDW, 09/15/2026: From $179
    15

    Tue

  • TUS–MDW, 09/16/2026: From $179
    16

    Wed

  • TUS–MDW, 09/17/2026: From $179
    17

    Thu

  • TUS–MDW: cmp-view-offers-disclaimer. Find Offers
    18

    Fri

  • TUS–MDW, 09/19/2026: From $179
    19

    Sat

  • TUS–MDW, 09/20/2026: From $251
    20

    Sun

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

    Mon

    • Range$179-$286

    *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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