Southwest® flights from Tucson to Chicago (Midway) from $209

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Low fares from Tucson to Chicago (Midway)

$

Tucson (TUS)to

Chicago (Midway) (MDW)
Depart: 09/11/2026

One-way

Basic

From
$209
Seen: 48 minutes ago

Tucson (TUS)to

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

One-way

Basic

From
$209
Seen: 7 hrs ago

Tucson (TUS)to

Chicago (Midway) (MDW)
Depart: 10/20/2026

One-way

Basic

From
$209
Seen: 7 hrs ago

Tucson (TUS)to

Chicago (Midway) (MDW)
Depart: 10/17/2026

One-way

Basic

From
$209
Seen: 2 hrs ago

Tucson (TUS)to

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

One-way

Basic

From
$209
Seen: 18 hrs ago

Tucson (TUS)to

Chicago (Midway) (MDW)
Depart: 11/05/2026

One-way

Basic

From
$217
Seen: 8 hrs ago

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Explore flights from Tucson to Chicago (Midway)

Aug 2026
From$227*
Seen: 21 hrs ago
One Way/Basic
Sep 2026
From$209*
Seen: 48 minutes ago
One Way/Basic
Oct 2026
From$209*
Seen: 18 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $227
cmp-daily-histogram-bars-legend-max-price-aria-label $440
Displaying fares for August-2026
  • TUS–MDW, 08/01/2026: From $440
    01

    Sat

    AUG

  • TUS–MDW, 08/02/2026: From $290
    02

    Sun

  • TUS–MDW, 08/03/2026: From $281
    03

    Mon

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    04

    Tue

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    05

    Wed

  • TUS–MDW, 08/06/2026: From $286
    06

    Thu

  • TUS–MDW, 08/07/2026: From $286
    07

    Fri

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    08

    Sat

  • TUS–MDW, 08/09/2026: From $286
    09

    Sun

  • TUS–MDW, 08/10/2026: From $286
    10

    Mon

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

    Tue

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    12

    Wed

  • TUS–MDW, 08/13/2026: From $286
    13

    Thu

  • TUS–MDW, 08/14/2026: From $286
    14

    Fri

  • TUS–MDW, 08/15/2026: From $248
    15

    Sat

  • TUS–MDW, 08/16/2026: From $286
    16

    Sun

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    17

    Mon

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    18

    Tue

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    19

    Wed

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    20

    Thu

  • TUS–MDW, 08/21/2026: From $251
    21

    Fri

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    22

    Sat

  • TUS–MDW, 08/23/2026: From $282
    23

    Sun

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    24

    Mon

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    25

    Tue

  • TUS–MDW, 08/26/2026: From $227
    26

    Wed

  • TUS–MDW, 08/27/2026: From $227
    27

    Thu

  • TUS–MDW, 08/28/2026: From $251
    28

    Fri

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    29

    Sat

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    30

    Sun

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    31

    Mon

    • Range$227-$440

    *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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