Southwest® flights from Chicago-Midway to Anchorage from $270

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Low fares from Chicago-Midway to Anchorage

$

Chicago-Midway (MDW)to

Anchorage (ANC)
Depart: 09/12/2026

One-way

Basic

From
$270
Seen: 13 hrs ago

Chicago-Midway (MDW)to

Anchorage (ANC)
Depart: 09/07/2026

One-way

Basic

From
$270
Seen: 11 hrs ago

Chicago-Midway (MDW)to

Anchorage (ANC)
Depart: 09/11/2026

One-way

Basic

From
$276
Seen: 13 hrs ago

Chicago-Midway (MDW)to

Anchorage (ANC)
Depart: 09/01/2026

One-way

Basic

From
$280
Seen: 3 hrs ago

Chicago-Midway (MDW)to

Anchorage (ANC)
Depart: 09/02/2026

One-way

Basic

From
$280
Seen: 3 hrs ago

Chicago-Midway (MDW)to

Anchorage (ANC)
Depart: 09/12/2026

One-way

Choice

From
$320
Seen: 13 hrs ago

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Explore flights from Chicago-Midway to Anchorage

Sep 2026
From$270*
Seen: 11 hrs ago
One Way/Basic
Oct 2026
No result for this month.
Nov 2026
No result for this month.
cmp-daily-histogram-bars-legend-min-price-aria-label $270
Displaying fares for September-2026
  • MDW–ANC, 09/01/2026: From $280
    01

    Tue

    SEP

  • MDW–ANC, 09/02/2026: From $280
    02

    Wed

  • MDW–ANC: cmp-view-offers-disclaimer. Find Offers
    03

    Thu

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    04

    Fri

  • MDW–ANC, 09/05/2026: From $323
    05

    Sat

  • MDW–ANC: cmp-view-offers-disclaimer. Find Offers
    06

    Sun

  • MDW–ANC, 09/07/2026: From $270
    07

    Mon

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

    Tue

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

    Wed

  • MDW–ANC, 09/10/2026: From $331
    10

    Thu

  • MDW–ANC, 09/11/2026: From $276
    11

    Fri

  • MDW–ANC, 09/12/2026: From $270
    12

    Sat

  • MDW–ANC, 09/13/2026: From $352
    13

    Sun

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    14

    Mon

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    15

    Tue

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    16

    Wed

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    17

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    18

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    19

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    20

    Sun

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    21

    Mon

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    22

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    23

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    24

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    25

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    26

    Sat

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    27

    Sun

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    28

    Mon

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    29

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    30

    Wed

    • Range$270-$352

    *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.

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