Southwest® flights from Chicago-Midway to Lihue, Kauai, Hawaii from $219

Promo Code

Low fares from Chicago-Midway to Lihue, Kauai, Hawaii

$

Chicago-Midway (MDW)to

Lihue, Kauai, Hawaii (LIH)
Depart: 11/12/2026

One-way

Basic

From
$219
Seen: 18 hrs ago

Chicago-Midway (MDW)to

Lihue, Kauai, Hawaii (LIH)
Depart: 11/10/2026

One-way

Basic

From
$225
Seen: 37 minutes ago

Chicago-Midway (MDW)to

Lihue, Kauai, Hawaii (LIH)
Depart: 12/03/2026

One-way

Basic

From
$225
Seen: 6 hrs ago

Chicago-Midway (MDW)to

Lihue, Kauai, Hawaii (LIH)
Depart: 10/30/2026

One-way

Basic

From
$225
Seen: 7 hrs ago

Chicago-Midway (MDW)to

Lihue, Kauai, Hawaii (LIH)
Depart: 09/11/2026

One-way

Basic

From
$242
Seen: 1 hour ago

Chicago-Midway (MDW)to

Lihue, Kauai, Hawaii (LIH)
Depart: 09/13/2026

One-way

Basic

From
$242
Seen: 8 hrs ago

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Explore flights from Chicago-Midway to Lihue, Kauai, Hawaii

Sep 2026
From$242*
Seen: 1 hour ago
One Way/Basic
Oct 2026
From$225*
Seen: 7 hrs ago
One Way/Basic
Nov 2026
From$219*
Seen: 18 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $242
Displaying fares for September-2026
  • MDW–LIH: cmp-view-offers-disclaimer. Find Offers
    10

    Thu

    SEP

  • MDW–LIH, 09/11/2026: From $242
    11

    Fri

  • MDW–LIH, 09/12/2026: From $368
    12

    Sat

  • MDW–LIH, 09/13/2026: From $242
    13

    Sun

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

    Mon

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

    Tue

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

    Wed

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

    Thu

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

    Fri

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

    Sat

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

    Sun

  • MDW–LIH, 09/21/2026: From $362
    21

    Mon

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

    Tue

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

    Wed

  • MDW–LIH: cmp-view-offers-disclaimer. Find Offers
    24

    Thu

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

    Fri

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

    Sat

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

    Sun

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

    Mon

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

    Tue

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

    Wed

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

    Thu

    OCT

  • MDW–LIH: cmp-view-offers-disclaimer. Find Offers
    02

    Fri

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

    Sat

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

    Sun

  • MDW–LIH, 10/05/2026: From $393
    05

    Mon

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

    Tue

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

    Wed

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

    Thu

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

    Fri

    • Range$242-$393

    *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:
    Chicago Midway International Airport
    Arriving at:
    Lihue Airport
    Distance:
    4298 miles

    Route Information

    37† Weekly flights

    † 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

    There are 37 weekly flights from Chicago (Midway) to Lihue (Kauai) on Southwest Airlines.
    To find the lowest fares by day and time to fly Chicago (Midway) to Lihue (Kauai) with Southwest, check out our Low Fare Calendar.
    You can rent a car at Lihue Airport book yours with your flight.
    Yes! Flights from Chicago (Midway) to Lihue (Kauai)—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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