Southwest® flights from Chicago (Midway) to Anchorage from $247

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Low fares from Chicago (Midway) to Anchorage

$

Chicago (Midway) (MDW)to

Anchorage (ANC)
Depart: 09/01/2026

One-way

Basic

From
$247
Seen: 17 hrs ago

Chicago (Midway) (MDW)to

Anchorage (ANC)
Depart: 09/02/2026

One-way

Basic

From
$253
Seen: 17 hrs ago

Chicago (Midway) (MDW)to

Anchorage (ANC)
Depart: 09/01/2026

One-way

Choice

From
$277
Seen: 17 hrs ago

Chicago (Midway) (MDW)to

Anchorage (ANC)
Depart: 09/02/2026

One-way

Choice

From
$283
Seen: 17 hrs ago

Chicago (Midway) (MDW)to

Anchorage (ANC)
Depart: 08/25/2026

One-way

Basic

From
$353
Seen: 18 hrs ago

Chicago (Midway) (MDW)to

Anchorage (ANC)
Depart: 09/05/2026

One-way

Basic

From
$358
Seen: 9 hrs ago

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Explore flights from Chicago (Midway) to Anchorage

Aug 2026
From$353*
Seen: 18 hrs ago
One Way/Basic
Sep 2026
From$247*
Seen: 17 hrs ago
One Way/Basic
Oct 2026
No result for this month.
cmp-daily-histogram-bars-legend-min-price-aria-label $247
cmp-daily-histogram-bars-legend-max-price-aria-label $432
Displaying fares for August-2026
  • MDW–ANC: cmp-view-offers-disclaimer. Find Offers
    11

    Tue

    AUG

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

    Wed

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

    Thu

  • MDW–ANC, 08/14/2026: From $422
    14

    Fri

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

    Sat

  • MDW–ANC: cmp-view-offers-disclaimer. Find Offers
    16

    Sun

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

    Mon

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

    Tue

  • MDW–ANC, 08/19/2026: From $365
    19

    Wed

  • MDW–ANC, 08/20/2026: From $432
    20

    Thu

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

    Fri

  • MDW–ANC, 08/22/2026: From $377
    22

    Sat

  • MDW–ANC, 08/23/2026: From $383
    23

    Sun

  • MDW–ANC, 08/24/2026: From $388
    24

    Mon

  • MDW–ANC, 08/25/2026: From $353
    25

    Tue

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

    Wed

  • MDW–ANC: cmp-view-offers-disclaimer. Find Offers
    27

    Thu

  • MDW–ANC, 08/28/2026: From $377
    28

    Fri

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

    Sat

  • MDW–ANC: cmp-view-offers-disclaimer. Find Offers
    30

    Sun

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

    Mon

  • MDW–ANC, 09/01/2026: From $247
    01

    Tue

    SEP

  • MDW–ANC, 09/02/2026: From $253
    02

    Wed

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

    Thu

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

    Fri

  • MDW–ANC, 09/05/2026: From $358
    05

    Sat

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

    Sun

  • MDW–ANC, 09/07/2026: From $365
    07

    Mon

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

    Tue

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

    Wed

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

    Thu

    • Range$247-$432

    *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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