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$377+ 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 5/28. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — LIH
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$543
(Southwest)

One-way from

$377
(Delta)

Popular in

December

Cheapest in

November

Average price

$648
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. 4% potential increase in price ($29 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($27 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 1, 2025.

This Delta deal was found by Cheapflights users on 4/30. 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.
Wed 6/47:25 pmMDW - LIH
2 stops28h 35mDelta
Tue 6/108:35 pmLIH - MDW
2 stops17h 06mDelta
Deal found 4/30$561
This Southwest deal was found by Cheapflights users on 4/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/79:45 pmMDW - LIH
1 stop17h 35mSouthwest
Fri 6/136:15 amLIH - MDW
2 stops13h 15mSouthwest
Deal found 4/30$778

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 May 1, 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

Wed 6/4

7:25 pm-7:00 pm

2 stops28h 35m

Lihue

Tue 6/10

8:35 pm-6:41 pm

2 stops17h 06m

$561

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Sat 6/7

9:45 pm-10:20 am

1 stop17h 35m

Lihue

Fri 6/13

6:15 am-12:30 am

2 stops13h 15m

$778

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Wed 5/28

9:16 am-7:00 pm

2 stops14h 44m

$377

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Tue 7/22

7:00 am-4:00 pm

2 stops14h 00m

$397

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

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

Rainfall in Kaua'i by month

Plan your trip to Kaua'i by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Kaua'i ranges from 2.2 - 6.7 inches per month. January is typically the wettest month, when rainfall can reach 6.7 in. June is typically the driest time to visit Kaua'i when rainfall is around 2.2 in.

Temperature in Kaua'i by month

Plan your trip to Kaua'i by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Kaua'i, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 77.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 69.8 F).

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 May 1, 2025.
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,294 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,934 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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.

  • 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 $678). 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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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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$750Average$863FlexibilityNo cancel feeOn-time63%

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