Southwest® flights from Eugene to Chicago-Midway from $141

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Low fares from Eugene to Chicago-Midway

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Eugene (EUG)to

Chicago-Midway (MDW)
Depart: 11/10/2026

One-way

Basic

From
$141
Seen: 3 hrs ago

Eugene (EUG)to

Chicago-Midway (MDW)
Depart: 11/10/2026

One-way

Choice

From
$192
Seen: 3 hrs ago

Eugene (EUG)to

Chicago-Midway (MDW)
Depart: 12/22/2026

One-way

Basic

From
$240
Seen: 3 hrs ago

Eugene (EUG)to

Chicago-Midway (MDW)
Depart: 11/10/2026

One-way

Choice Preferred

From
$273
Seen: 3 hrs ago

Eugene (EUG)to

Chicago-Midway (MDW)
Depart: 12/27/2026

One-way

Basic

From
$289
Seen: 11 hrs ago

Eugene (EUG)to

Chicago-Midway (MDW)
Depart: 11/16/2026

One-way

Basic

From
$289
Seen: 2 hrs ago

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Explore flights from Eugene to Chicago-Midway

Oct 2026
From$305*
Seen: 23 hrs ago
One Way/Basic
Nov 2026
From$141*
Seen: 3 hrs ago
One Way/Basic
Dec 2026
From$240*
Seen: 3 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $141
Displaying fares for October-2026
  • EUG–MDW: cmp-view-offers-disclaimer. Find Offers
    21

    Wed

    OCT

  • EUG–MDW, 10/22/2026: From $370
    22

    Thu

  • EUG–MDW, 10/23/2026: From $370
    23

    Fri

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    24

    Sat

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    25

    Sun

  • EUG–MDW, 10/26/2026: From $370
    26

    Mon

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

    Tue

  • EUG–MDW: cmp-view-offers-disclaimer. Find Offers
    28

    Wed

  • EUG–MDW, 10/29/2026: From $305
    29

    Thu

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

    Fri

  • EUG–MDW, 10/31/2026: From $305
    31

    Sat

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    01

    Sun

    NOV

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    02

    Mon

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    03

    Tue

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    04

    Wed

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    05

    Thu

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    06

    Fri

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    07

    Sat

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

    Sun

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

    Mon

  • EUG–MDW, 11/10/2026: From $141
    10

    Tue

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

    Wed

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

    Thu

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

    Fri

  • EUG–MDW: cmp-view-offers-disclaimer. Find Offers
    14

    Sat

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

    Sun

  • EUG–MDW, 11/16/2026: From $289
    16

    Mon

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

    Tue

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

    Wed

  • EUG–MDW: cmp-view-offers-disclaimer. Find Offers
    19

    Thu

  • EUG–MDW: cmp-view-offers-disclaimer. Find Offers
    20

    Fri

    • Range$141-$370

    *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:
    Eugene Airport
    Arriving at:
    Chicago Midway International Airport
    Distance:
    1791 miles

    Questions we hear the most

    There are 69 weekly flights from Eugene to Chicago (Midway) on Southwest Airlines.
    To find the lowest fares by day and time to fly Eugene 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 Eugene 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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