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

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Low fares from Tucson to Chicago-Midway

$

Tucson (TUS)to

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

One-way

Basic

From
$199
Seen: 23 hrs ago

Tucson (TUS)to

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

One-way

Basic

From
$199
Seen: 22 hrs ago

Tucson (TUS)to

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

One-way

Basic

From
$199
Seen: 4 hrs ago

Tucson (TUS)to

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

One-way

Basic

From
$199
Seen: 11 hrs ago

Tucson (TUS)to

Chicago-Midway (MDW)
Depart: 12/17/2026

One-way

Basic

From
$199
Seen: 11 hrs ago

Tucson (TUS)to

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

One-way

Basic

From
$199
Seen: 16 hrs ago

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Explore flights from Tucson to Chicago-Midway

Sep 2026
From$209*
Seen: 22 hrs ago
One Way/Basic
Oct 2026
From$199*
Seen: 3 hrs ago
One Way/Basic
Nov 2026
From$199*
Seen: 22 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $209
cmp-daily-histogram-bars-legend-max-price-aria-label $341
Displaying fares for September-2026
  • TUS–MDW: cmp-view-offers-disclaimer. Find Offers
    11

    Fri

    SEP

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

    Sat

  • TUS–MDW, 09/13/2026: From $296
    13

    Sun

  • TUS–MDW, 09/14/2026: From $296
    14

    Mon

  • TUS–MDW, 09/15/2026: From $258
    15

    Tue

  • TUS–MDW, 09/16/2026: From $258
    16

    Wed

  • TUS–MDW, 09/17/2026: From $296
    17

    Thu

  • TUS–MDW, 09/18/2026: From $296
    18

    Fri

  • TUS–MDW, 09/19/2026: From $258
    19

    Sat

  • TUS–MDW, 09/20/2026: From $296
    20

    Sun

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

    Mon

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

    Tue

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

    Wed

  • TUS–MDW, 09/24/2026: From $296
    24

    Thu

  • TUS–MDW: cmp-view-offers-disclaimer. Find Offers
    25

    Fri

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

    Sat

  • TUS–MDW, 09/27/2026: From $296
    27

    Sun

  • TUS–MDW, 09/28/2026: From $296
    28

    Mon

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

    Tue

  • TUS–MDW, 09/30/2026: From $209
    30

    Wed

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

    Thu

    OCT

  • TUS–MDW, 10/02/2026: From $237
    02

    Fri

  • TUS–MDW, 10/03/2026: From $209
    03

    Sat

  • TUS–MDW, 10/04/2026: From $341
    04

    Sun

  • TUS–MDW: cmp-view-offers-disclaimer. Find Offers
    05

    Mon

  • TUS–MDW, 10/06/2026: From $209
    06

    Tue

  • TUS–MDW: cmp-view-offers-disclaimer. Find Offers
    07

    Wed

  • TUS–MDW: cmp-view-offers-disclaimer. Find Offers
    08

    Thu

  • TUS–MDW: cmp-view-offers-disclaimer. Find Offers
    09

    Fri

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

    Sat

    • Range$209-$341

    *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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