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Kaua'i

$217+ 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 2/8. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — LIH
Dec 20 — Dec 271
Sat 12/20
Sat 12/27
1 adult, Economy
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Find 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 November 20, 2025.

This Delta deal was found by Cheapflights users on 11/20. 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 12/99:34 amMDW - LIH
2 stops14h 36mDelta
Sun 12/149:50 pmLIH - MDW
2 stops16h 28mDelta
Deal found 11/20$407
This Delta deal was found by Cheapflights users on 11/19. 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.
Sun 12/79:34 amMDW - LIH
2 stops14h 36mDelta
Sun 12/149:50 pmLIH - MDW
2 stops16h 28mDelta
Deal found 11/19$427
This Southwest deal was found by Cheapflights users on 11/19. 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.
Tue 12/95:15 amMDW - LIH
1 stop12h 00mSouthwest
Sun 12/149:10 pmLIH - MDW
1 stop12h 30mSouthwest
Deal found 11/19$605
This Delta deal was found by Cheapflights users on 11/18. 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.
Thu 11/276:00 amMDW - LIH
2 stops18h 30mDelta
Fri 12/59:50 pmLIH - MDW
2 stops16h 28mDelta
Deal found 11/18$656
This Delta deal was found by Cheapflights users on 11/18. 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 12/36:00 amMDW - LIH
2 stops18h 30mDelta
Sun 12/710:55 pmLIH - MDW
2 stops15h 23mDelta
Deal found 11/18$716
This Delta deal was found by Cheapflights users on 11/18. 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 11/199:34 amMDW - LIH
2 stops14h 30mDelta
Fri 5/159:45 pmLIH - MDW
2 stops15h 46mDelta
Deal found 11/18$734
This Delta deal was found by Cheapflights users on 11/19. 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.
Wed 12/36:00 amMDW - LIH
2 stops18h 30mDelta
Sat 12/69:50 pmLIH - MDW
2 stops16h 28mDelta
Deal found 11/19$736
This Southwest deal was found by Cheapflights users on 11/18. 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 12/35:15 amMDW - LIH
1 stop12h 00mSouthwest
Sun 12/79:10 pmLIH - MDW
1 stop12h 30mSouthwest
Deal found 11/18$738

Cheap 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 November 20, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$407
(Delta)

One-way from

$217
(Delta)

Popular in

December

Cheapest in

October

Average price

$563
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. 4% potential increase in price ($30 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($30 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
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 November 20, 2025.
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

Tue 12/9

9:34 am-8:10 pm

2 stops14h 36m

Lihue

Sun 12/14

9:50 pm-6:18 pm

2 stops16h 28m

$407

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Tue 1/20

9:32 am-7:55 pm

2 stops14h 23m

Lihue

Tue 2/17

9:31 pm-5:37 pm

2 stops16h 06m

$564

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Wed 2/18

5:05 am-2:25 pm

2 stops13h 20m

Lihue

Wed 2/25

7:05 pm-12:15 pm

2 stops13h 10m

$580

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Tue 12/9

5:15 am-1:15 pm

1 stop12h 00m

Lihue

Sun 12/14

9:10 pm-1:40 pm

1 stop12h 30m

$605

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Sun 1/11

8:10 am-4:25 pm

1 stop12h 15m

Lihue

Sat 1/17

9:15 pm-2:45 pm

2 stops13h 30m

$715

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Wed 12/3

6:00 am-8:30 pm

2 stops18h 30m

Lihue

Sun 12/7

10:55 pm-6:18 pm

2 stops15h 23m

$716

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Thu 1/15

9:32 am-7:55 pm

2 stops14h 23m

Lihue

Wed 1/21

10:45 pm-6:36 pm

2 stops15h 51m

$732

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Wed 12/3

5:15 am-1:15 pm

1 stop12h 00m

Lihue

Sun 12/7

9:10 pm-1:40 pm

1 stop12h 30m

$738

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Sun 2/8

9:33 am-7:55 pm

2 stops14h 22m

$217

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Mon 12/15

3:52 pm-11:34 am

2 stops23h 42m

$245

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/18

Showing 1-10 of 19 results
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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.

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 Delta and Southwest fly from Chicago Midway Airport to Kaua'i in about 13h 20m. The time it takes to get you to your destination can typically vary by up to 1h 16m. 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

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