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$375+ Cheap flights from Kaua'i to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/30. Fares are subject to change and may not be available on all flights or dates of travel.
LIH — MDW
Nov 1 — Nov 81
Sat 11/1
Sat 11/8
1 adult, Economy
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Cheap flight deals from Kaua'i to Midway

Keep the following information in mind while searching for Kaua'i to Midway flight deals. Data was last updated October 2, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$848
(Delta)

One-way from

$375
(Kiwi.com)
Provider with most accurate pricing for Lihue-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Lihue-Chicago (CHI) flights.
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From Kaua'i to Chicago Midway
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One-way flight from Kaua'i to Chicago Midway
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Find flight deals from Kaua'i to Midway

Cheapest flights from Kaua'i to Midway
Explore the most affordable flight options available from Kaua'i to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 2, 2025.

This Delta deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/308:32 pmLIH - MDW
2 stops16h 03mDelta
Thu 10/29:35 amMDW - LIH
2 stops14h 24mDelta
Deal found 9/29$713
This Delta deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/19:40 pmLIH - MDW
2 stops16h 20mDelta
Wed 12/109:34 amMDW - LIH
2 stops14h 36mDelta
Deal found 9/30$848
This Delta deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/158:30 pmLIH - MDW
2 stops16h 13mDelta
Sun 10/196:00 amMDW - LIH
2 stops18h 05mDelta
Deal found 9/30$1,991

Cheapflights Fare Finder

 
Customize your flight search to find flights from Kaua'i to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated October 2, 2025.
Use the filters below to find and compare flights from Kaua'i to Chicago Midway Airport that are best for you.

Fly from

Kaua'i

Fly to

Midway

Route

Depart

Return

Price

LihueChicago

LIH - MDW

LIHMDW

Lihue

Mon 12/1

9:40 pm-6:00 pm

2 stops16h 20m

Chicago Midway

Wed 12/10

9:34 am-8:10 pm

2 stops14h 36m

$848

LihueChicago

LIH - MDW

LIHMDW

Lihue

Wed 10/15

8:30 pm-5:43 pm

2 stops16h 13m

Chicago Midway

Sun 10/19

6:00 am-7:05 pm

2 stops18h 05m

$1,991

LihueChicago

LIH - MDW

LIHMDW

Lihue

Mon 3/30

1:32 pm-1:01 pm

2 stops18h 29m

$375

LihueChicago

LIH - MDW

LIHMDW

Lihue

Mon 3/30

8:40 pm-11:55 am

1 stop10h 15m

$457

LihueChicago

LIH - MDW

LIHMDW

Lihue

Sat 3/28

6:15 pm-1:59 pm

3 stops38h 44m

$533

LihueChicago

LIH - MDW

LIHMDW

Lihue

Mon 1/5

8:28 am-10:15 pm

3 stops57h 47m

$544

LihueChicago

LIH - MDW

LIHMDW

Lihue

Sun 3/29

9:45 pm-1:08 pm

2 stops34h 23m

$546

LihueChicago

LIH - MDW

LIHMDW

Lihue

Thu 1/1

6:10 pm-11:05 pm

3 stops24h 55m

$681

LihueChicago

LIH - MDW

LIHMDW

Lihue

Sat 3/28

6:15 pm-9:56 am

2 stops34h 41m

$706

LihueChicago

LIH - MDW

LIHMDW

Lihue

Sat 3/28

8:40 pm-3:00 pm

1 stop13h 20m

$804

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/30

Showing 1-10 of 11 results
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Best time to book a flight from Kaua'i to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Kaua'i with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Kaua'i to Chicago Midway Airport
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Kaua'i to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Kaua'i to Chicago Midway Airport?

    Delta can get you from Kaua'i to Chicago Midway Airport in just under 16h 20m. Your travel time can differ by up to . Kaua'i and Chicago Midway Airport are separated by a distance of 4289 mi.

  • Can I find deals for flights from Kaua'i to Midway that include hotel bookings?

    Yes. In addition to deals on Kaua'i to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Kaua'i to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Kaua'i to Midway.

  • Can I find deals for business class flights from Kaua'i to Midway?

    Yes. Cheapflights offers flight deals from Kaua'i to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Kaua'i to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Kaua'i to Chicago Midway Airport (average of $160). Flying from Kaua'i to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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