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Midway

$218+ 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 2/6. Fares are subject to change and may not be available on all flights or dates of travel.
LIH — MDW
feb. 20 — feb. 271
vie. 2/20
vie. 2/27
1 adult, Economy
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Cheap 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 enero 21, 2026.

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.
vie. 2/69:20 pm
LIH
-
MDW
2 stops14h 56m
Delta
lun. 2/96:00 am
MDW
-
LIH
2 stops18h 30m
Delta
Deal found 1/20$658
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.
dom. 3/17:05 pm
LIH
-
MDW
2 stops13h 25m
Southwest
sáb. 3/710:10 am
MDW
-
LIH
2 stops15h 10m
Southwest
Deal found 1/20$695
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.
mié. 2/410:39 pm
LIH
-
MDW
2 stops15h 57m
Delta
dom. 2/86:00 am
MDW
-
LIH
2 stops18h 30m
Delta
Deal found 1/20$738
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.
vie. 5/229:26 pm
LIH
-
MDW
2 stops16h 05m
Delta
dom. 5/319:30 am
MDW
-
LIH
2 stops14h 50m
Delta
Deal found 1/20$1,305

Find 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 enero 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
1 star

Round-trip from

$658
(Delta)

One-way from

$218
(Delta)
Provider with most accurate pricing for Lihue-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Lihue-Chicago (CHI) flights.
Search Deals
From Kaua'i to Chicago Midway
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One-way flight from Kaua'i to Chicago Midway
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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 enero 21, 2026.
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

vie. 2/6

9:20 pm-4:16 pm

2 stops14h 56m

Chicago Midway

lun. 2/9

6:00 am-8:30 pm

2 stops18h 30m

$658

LihueChicago

LIH - MDW

LIHMDW

Lihue

dom. 3/1

7:05 pm-12:30 pm

2 stops13h 25m

Chicago Midway

sáb. 3/7

10:10 am-9:20 pm

2 stops15h 10m

$695

LihueChicago

LIH - MDW

LIHMDW

Lihue

vie. 5/22

9:26 pm-6:31 pm

2 stops16h 05m

Chicago Midway

dom. 5/31

9:30 am-7:20 pm

2 stops14h 50m

$1,305

LihueChicago

LIH - MDW

LIHMDW

Lihue

vie. 2/6

9:20 pm-4:16 pm

2 stops14h 56m

$218

LihueChicago

LIH - MDW

LIHMDW

Lihue

vie. 5/1

8:25 pm-6:45 pm

2 stops17h 20m

$288

LihueChicago

LIH - MDW

LIHMDW

Lihue

vie. 2/6

9:15 pm-11:50 am

1 stop10h 35m

$312

LihueChicago

LIH - MDW

LIHMDW

Lihue

vie. 2/6

6:33 pm-11:13 pm

3 stops48h 40m

$318

LihueChicago

LIH - MDW

LIHMDW

Lihue

dom. 3/15

9:10 pm-6:05 pm

2 stops15h 55m

$363

LihueChicago

LIH - MDW

LIHMDW

Lihue

dom. 3/15

11:02 am-6:13 pm

3 stops50h 11m

$374

LihueChicago

LIH - MDW

LIHMDW

Lihue

lun. 4/6

10:05 pm-8:53 am

2 stops29h 48m

$386

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

Showing 1-10 of 13 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 and Southwest can get you from Kaua'i to Chicago Midway Airport in just under 13h 25m. Your travel time can differ by up to 1h 31m. Kaua'i and Chicago Midway Airport are separated by 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 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.

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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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