$247 Find Cheap Flights from Chicago Midway Airport to Kaua'i

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Kaua'i departing on 9/27. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Kaua'i

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Kaua'i, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Kaua'i, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Midway to Kaua'i

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Lihue
Lihue1 stop$428
Lihue
Lihue1 stop$428

Book Cheap Midway to Kaua'i Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Kaua'i that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Kaua'i

Thu, Mar 5 - Tue, Mar 10
Southwest Logo
10:05 am - 5:10 pmMDW-LIH
11h 05m1 stop
Southwest Logo
11:50 am - 5:55 amLIH-MDW
13h 05m2 stops
$428Southwest
Find Deal
Mon, Feb 2 - Wed, Feb 11
Southwest Logo
5:05 am - 2:25 pmMDW-LIH
13h 20m2 stops
Southwest Logo
9:15 pm - 3:00 pmLIH-MDW
13h 45m1 stop
$475Southwest
Find Deal
Mon, Feb 2 - Wed, Feb 11
Southwest Logo
5:05 am - 2:25 pmMDW-LIH
13h 20m2 stops
Southwest Logo
9:15 pm - 12:55 pmLIH-MDW
11h 40m2 stops
$480Southwest
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Thu, Mar 5 - Tue, Mar 10
Southwest Logo
10:05 am - 5:10 pmMDW-LIH
11h 05m1 stop
Southwest Logo
8:40 pm - 11:55 amLIH-MDW
10h 15m1 stop
$498Southwest
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Tue, Feb 3 - Tue, Feb 10
Southwest Logo
5:05 am - 2:25 pmMDW-LIH
13h 20m2 stops
Southwest Logo
9:15 pm - 12:35 pmLIH-MDW
11h 20m1 stop
$520Southwest
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Tue, Feb 3 - Tue, Feb 10
Southwest Logo
5:05 am - 2:25 pmMDW-LIH
13h 20m2 stops
Southwest Logo
9:15 pm - 2:45 pmLIH-MDW
13h 30m2 stops
$525Southwest
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Sun, Dec 7 - Sat, Dec 13
Southwest Logo
7:45 am - 4:15 pmMDW-LIH
12h 30m1 stop
Southwest Logo
9:10 pm - 4:20 pmLIH-MDW
15h 10m2 stops
$528Southwest
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Sun, Dec 7 - Sat, Dec 13
Southwest Logo
7:45 am - 4:15 pmMDW-LIH
12h 30m1 stop
Southwest Logo
9:10 pm - 1:05 pmLIH-MDW
11h 55m1 stop
$548Southwest
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Sun, Oct 26 - Sun, Nov 2
Delta Logo
9:35 am - 7:05 pmMDW-LIH
14h 30m2 stops
Delta Logo
10:40 pm - 5:43 pmLIH-MDW
15h 03m2 stops
$564Delta
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Tue, Feb 24 - Wed, Mar 4
Delta Logo
9:30 am - 8:31 pmMDW-LIH
15h 01m2 stops
Delta Logo
10:26 pm - 6:34 pmLIH-MDW
16h 08m2 stops
$604Delta
Find Deal
Booking Insights

KAYAK's insights & trends for Midway to Kaua'i flights

Get data-powered insights and trends into flights from Midway to Kaua'i to help you find the cheapest flights, the best time to fly and much more.

Can I save money by flying with a layover from Chicago Midway Airport to Kaua'i?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $321, prices are generally cheapest when you fly direct.

Good to know

Cheapest flight$247
Flight from Chicago Midway Airport to Lihue

FAQs - booking Kaua'i flights

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Kaua'i?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to Kaua'i.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Kaua'i?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago Midway Airport to Kaua'i is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to Kaua'i?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Chicago Midway Airport to Kaua'i with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Kaua'i?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Chicago Midway Airport to Kaua'i up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Kaua'i?

    The cheapest time of day to fly to Kaua'i is generally in the morning, when round-trip flights cost $831 on average. The most expensive time of day to fly to Kaua'i is generally in the morning, which is peak travel time and where the average cost of a ticket is $831.

Reviews of the top airline flying from Midway to Kaua'i

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Kaua'i. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to Kaua'i? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4242 reviews
7.5Entertainment
8.1Boarding
8.0Comfort
8.6Crew
7.0Food
Airline reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

10.0 ExcellentG, Sep 2025LAS - ATL
Read more Southwest reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Everything you need to know for your flight to Kaua'i

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