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$297+ 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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — LIH
Nov 1 — Nov 81
Sat 11/1
Sat 11/8
1 adult, Economy
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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 October 2, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$434
(Delta)

One-way from

$297
(Delta)

Popular in

December

Cheapest in

October

Average price

$510
Provider with most accurate pricing for Chicago (CHI)-Lihue flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Lihue flights.
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From Chicago Midway to Kaua'i
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One-way flight from Chicago Midway to Kaua'i
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Highest demand for flights based on searches. 2% potential increase in price ($14 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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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 October 2, 2025.

This Delta deal was found by Cheapflights users on 10/1. 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 10/289:35 amMDW - LIH
2 stops14h 30mDelta
Tue 11/49:30 pmLIH - MDW
2 stops16h 13mDelta
Deal found 10/1$434
This Delta deal was found by Cheapflights users on 10/1. 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 10/299:35 amMDW - LIH
2 stops14h 30mDelta
Wed 11/129:40 pmLIH - MDW
2 stops16h 28mDelta
Deal found 10/1$526
This Southwest deal was found by Cheapflights users on 10/1. 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 10/268:10 amMDW - LIH
1 stop12h 50mSouthwest
Sun 11/29:10 pmLIH - MDW
2 stops13h 50mSouthwest
Deal found 10/1$531
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.
Sun 10/269:35 amMDW - LIH
2 stops14h 30mDelta
Sun 11/29:30 pmLIH - MDW
2 stops16h 13mDelta
Deal found 9/30$554
This Southwest deal was found by Cheapflights users on 10/1. 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 10/77:10 amMDW - LIH
2 stops13h 50mSouthwest
Tue 10/77:05 pmLIH - MDW
2 stops12h 20mSouthwest
Deal found 10/1$609
This Delta deal was found by Cheapflights users on 10/1. 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 10/1$620
This Delta deal was found by Cheapflights users on 10/2. 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.
Fri 11/289:34 amMDW - LIH
2 stops14h 30mDelta
Mon 12/810:55 pmLIH - MDW
2 stops15h 23mDelta
Deal found 10/2$624
This Southwest deal was found by Cheapflights users on 10/1. 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 10/207:45 amMDW - LIH
1 stop13h 15mSouthwest
Sat 11/110:00 amLIH - MDW
2 stops13h 25mSouthwest
Deal found 10/1$628
This Southwest deal was found by Cheapflights users on 10/1. 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 10/77:10 amMDW - LIH
2 stops13h 50mSouthwest
Tue 10/147:05 pmLIH - MDW
2 stops13h 25mSouthwest
Deal found 10/1$634
This Delta deal was found by Cheapflights users on 10/2. 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 10/236:00 amMDW - LIH
2 stops18h 26mDelta
Tue 10/288:30 pmLIH - MDW
2 stops16h 13mDelta
Deal found 10/2$636
This Southwest deal was found by Cheapflights users on 10/2. 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 10/67:45 amMDW - LIH
1 stop13h 15mSouthwest
Mon 10/138:40 pmLIH - MDW
1 stop12h 25mSouthwest
Deal found 10/2$648

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 October 2, 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

Mon 1/19

5:10 am-1:15 pm

1 stop12h 05m

Lihue

Tue 4/14

8:40 pm-2:10 pm

1 stop12h 30m

$543

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Sun 10/26

8:10 am-4:00 pm

1 stop12h 50m

Lihue

Sun 11/2

9:10 pm-11:35 am

1 stop10h 25m

$551

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Wed 1/14

9:30 am-8:31 pm

2 stops15h 01m

Lihue

Tue 4/14

9:26 pm-6:05 pm

2 stops15h 39m

$554

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Mon 1/19

9:30 am-8:31 pm

2 stops15h 01m

Lihue

Tue 4/14

9:26 pm-6:05 pm

2 stops15h 39m

$554

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Sun 1/18

9:30 am-8:31 pm

2 stops15h 01m

Lihue

Tue 4/14

9:26 pm-6:05 pm

2 stops15h 39m

$554

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Tue 2/24

9:30 am-8:31 pm

2 stops15h 01m

Lihue

Wed 3/4

10:26 pm-6:34 pm

2 stops16h 08m

$554

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Mon 1/26

5:05 am-2:25 pm

2 stops13h 20m

Lihue

Tue 4/14

8:40 pm-2:15 pm

2 stops12h 35m

$555

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Sun 1/25

8:10 am-4:25 pm

1 stop12h 15m

Lihue

Thu 2/5

9:15 pm-1:45 pm

1 stop12h 30m

$568

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Tue 1/13

6:10 am-9:20 pm

2 stops19h 10m

Lihue

Tue 4/14

8:40 pm-2:10 pm

1 stop12h 30m

$574

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Wed 2/25

5:05 am-4:25 pm

2 stops15h 20m

Lihue

Mon 3/2

9:15 pm-12:35 pm

1 stop11h 20m

$574

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/29

Showing 1-10 of 20 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 Southwest and Delta fly from Chicago Midway Airport to Kaua'i in about 12h 05m. The time it takes to get you to your destination can typically vary by up to 2h 56m. 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.

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

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Kaua'i (average of $440). Flying from Chicago Midway Airport to Kaua'i in June is currently the most expensive (average of $689). 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

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