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Midway

$231+ 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 9/10. Fares are subject to change and may not be available on all flights or dates of travel.
LIH — MDW
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Find flight deals from Kaua'i to Midway

One-way flights from Kaua'i to Midway
Search for one-way flight options from Kaua'i to Midway. Find affordable one-way fares based on user searches. Data last updated August 14, 2025.

This Southwest deal was found by Cheapflights users on 8/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/108:40 pmLIH - MDW
1 stop12h 50mSouthwest
Deal found 8/13$231
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/311:48 pmLIH - MDW
2 stops22h 32mMultiple Airlines
Deal found 8/12$315
This Southwest deal was found by Cheapflights users on 8/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/308:40 pmLIH - MDW
2 stops14h 50mSouthwest
Deal found 8/12$332
This Delta deal was found by Cheapflights users on 8/14. 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
Deal found 8/14$336
This Southwest deal was found by Cheapflights users on 8/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/139:10 pmLIH - MDW
2 stops15h 10mSouthwest
Deal found 8/13$377
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1310:56 amLIH - MDW
3 stops22h 40mMultiple Airlines
Deal found 8/13$526

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 August 14, 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

Wed 9/10

8:40 pm-2:30 pm

1 stop12h 50m

$231

LihueChicago

LIH - MDW

LIHMDW

Lihue

Fri 10/31

1:48 pm-5:20 pm

2 stops22h 32m

$315

LihueChicago

LIH - MDW

LIHMDW

Lihue

Fri 10/31

8:40 pm-12:00 pm

1 stop10h 20m

$332

LihueChicago

LIH - MDW

LIHMDW

Lihue

Tue 9/30

8:40 pm-4:30 pm

2 stops14h 50m

$332

LihueChicago

LIH - MDW

LIHMDW

Lihue

Tue 9/30

8:32 pm-5:35 pm

2 stops16h 03m

$336

LihueChicago

LIH - MDW

LIHMDW

Lihue

Sat 12/13

9:10 pm-4:20 pm

2 stops15h 10m

$377

LihueChicago

LIH - MDW

LIHMDW

Lihue

Sat 12/13

10:56 am-1:36 pm

3 stops22h 40m

$526

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/13

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.

  • 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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