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Kaua'i

$260+ Cheap flights from Midway (MDW) to Kaua'i

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.
MDW — LIH
Feb 20 — Feb 271
Fri 2/20
Fri 2/27
1 adult, Economy
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Cheap flight deals from Midway to Kaua'i

Cheapest flights from Midway to Kaua'i
Explore the most affordable flight options available from Midway to Kaua'i. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 21, 2026.

This Southwest deal was found by Cheapflights users on 1/20. 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.
Mon 3/28:10 am
MDW
-
LIH
1 stop12h 15m
Southwest
Thu 3/59:20 pm
LIH
-
MDW
1 stop10h 25m
Southwest
Deal found 1/20$405
This Delta deal was found by Cheapflights users on 1/21. 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 2/249:34 am
MDW
-
LIH
2 stops14h 15m
Delta
Tue 3/1010:05 pm
LIH
-
MDW
2 stops14h 49m
Delta
Deal found 1/21$435
This Delta deal was found by Cheapflights users on 1/21. 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 2/249:34 am
MDW
-
LIH
2 stops14h 15m
Delta
Wed 3/410:40 pm
LIH
-
MDW
2 stops14h 57m
Delta
Deal found 1/21$481
This Delta deal was found by Cheapflights users on 1/19. 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 2/39:33 am
MDW
-
LIH
2 stops14h 21m
Delta
Mon 2/910:39 pm
LIH
-
MDW
2 stops15h 57m
Delta
Deal found 1/19$485
This Southwest deal was found by Cheapflights users on 1/19. 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.
Mon 2/98:10 am
MDW
-
LIH
1 stop12h 15m
Southwest
Fri 2/137:05 pm
LIH
-
MDW
2 stops14h 20m
Southwest
Deal found 1/19$500
This Southwest deal was found by Cheapflights users on 1/20. 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.
Thu 2/267:55 am
MDW
-
LIH
2 stops14h 20m
Southwest
Thu 3/59:20 pm
LIH
-
MDW
2 stops16h 40m
Southwest
Deal found 1/20$525
This Southwest deal was found by Cheapflights users on 1/19. 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.
Sun 5/35:10 am
MDW
-
LIH
2 stops16h 00m
Southwest
Wed 5/138:10 pm
LIH
-
MDW
1 stop12h 00m
Southwest
Deal found 1/19$529
This Delta deal was found by Cheapflights users on 1/20. 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 1/219:50 am
MDW
-
LIH
2 stops14h 05m
Delta
Wed 4/158:25 pm
LIH
-
MDW
2 stops17h 20m
Delta
Deal found 1/20$534
This Delta deal was found by Cheapflights users on 1/20. 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 9/229:30 am
MDW
-
LIH
2 stops14h 50m
Delta
Mon 9/289:26 pm
LIH
-
MDW
2 stops16h 05m
Delta
Deal found 1/20$535

Find flight deals from Midway to Kaua'i

Keep the following information in mind while searching for Midway to Kaua'i flight deals. Data was last updated January 21, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$405
(Southwest)

One-way from

$260
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$503
Provider with most accurate pricing for Chicago (CHI)-Lihue flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Lihue flights.
Search Deals
From Chicago Midway to Kaua'i
Search Deals
One-way flight from Chicago Midway to Kaua'i
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($85 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($47 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Kaua'i 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 January 21, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Kaua'i that are best for you.

Fly from

Midway

Fly to

Kaua'i

Route

Depart

Return

Price

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Mon 3/2

8:10 am-4:25 pm

1 stop12h 15m

Lihue

Thu 3/5

9:20 pm-6:00 pm

2 stops16h 40m

$431

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Tue 2/24

9:34 am-7:49 pm

2 stops14h 15m

Lihue

Wed 3/4

10:40 pm-5:37 pm

2 stops14h 57m

$435

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Tue 2/24

9:34 am-7:49 pm

2 stops14h 15m

Lihue

Tue 3/10

8:21 pm-6:40 pm

2 stops17h 19m

$480

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Tue 2/3

9:33 am-7:54 pm

2 stops14h 21m

Lihue

Mon 2/9

10:39 pm-6:36 pm

2 stops15h 57m

$485

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Thu 2/26

7:55 am-6:15 pm

2 stops14h 20m

Lihue

Thu 3/5

9:20 pm-11:45 am

1 stop10h 25m

$500

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Mon 2/9

8:10 am-4:25 pm

1 stop12h 15m

Lihue

Fri 2/13

7:05 pm-1:25 pm

2 stops14h 20m

$500

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Fri 1/30

6:10 am-9:20 pm

2 stops19h 10m

Lihue

Thu 2/5

7:05 pm-12:30 pm

2 stops13h 25m

$536

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Tue 2/24

9:34 am-7:49 pm

2 stops14h 15m

Lihue

Tue 3/3

9:20 pm-6:40 pm

2 stops17h 20m

$545

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Mon 3/30

10:36 pm-10:21 pm

3 stops28h 45m

$260

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Sat 4/11

6:25 pm-11:00 am

2 stops45h 35m

$270

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Showing 1-10 of 15 results
1
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Best time to book a flight from Midway to Kaua'i

Have a flexible travel schedule? Discover the best time to fly to Kaua'i from Midway 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 Chicago Midway Airport to Kaua'i
No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Kaua'i

Get insights into the airlines that provide service to Kaua'i. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Kaua'i. Reviews last updated January 21, 2026.
Read reviews from past customers who have flown Southwest from Chicago Midway Airport to Kaua'i. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,266 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,266 reviews
Southwest
8.0
Very good
4,266 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

Find useful and relevant information for your journey from Midway to Kaua'i. 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 Chicago Midway Airport to Kaua'i?

    Airlines like Southwest and Delta fly from Chicago Midway Airport to Kaua'i in about 12h 15m. The time it takes to get you to your destination can typically vary by up to 2h. Airlines will cover a distance of 4289 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

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

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

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

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

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

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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Top airline flying from Midway to Kaua'i

Discover the top airline that operate flights from Midway to Kaua'i. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$468Average$863FlexibilityNo cancel feeOn-time63%

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