$332 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 8/17. 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.
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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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Flights Deals

Best Kaua'i Flight Deals from Midway

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Lihue
Lihue2 stops$594
Lihue
Lihue2 stops$594

Cheap Flights from Midway to Kaua'i

 
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.

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

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Midway to Kaua'i.
Discover the best prices for you by selecting your travel dates on KAYAK.
Delta Logo
9:30 am - 7:22 pmMDW-LIH
14h 52m2 stops
Delta Logo
9:26 pm - 6:36 pmLIH-MDW
16h 10m2 stops
$594Delta
Find Deal
Thu, Oct 23 - Tue, Oct 28
Southwest Logo
5:10 am - 12:50 pmMDW-LIH
12h 40m1 stop
Southwest Logo
8:40 pm - 1:15 pmLIH-MDW
11h 35m1 stop
$623Southwest
Find Deal
Mon, Sep 1 - Tue, Sep 2
Delta Logo
9:16 am - 7:00 pmMDW-LIH
14h 44m2 stops
Delta Logo
8:35 pm - 5:40 pmLIH-MDW
16h 05m2 stops
$634Delta
Find Deal
Tue, Jun 3 - Tue, Jun 10
Southwest Logo
5:20 am - 4:00 pmMDW-LIH
15h 40m2 stops
Southwest Logo
8:30 am - 11:50 pmLIH-MDW
10h 20m1 stop
$638Southwest
Find Deal
Sat, May 10 - Sat, May 17
Southwest Logo
5:20 am - 4:00 pmMDW-LIH
15h 40m2 stops
Southwest Logo
10:00 am - 5:20 amLIH-MDW
14h 20m2 stops
$644Southwest
Find Deal
Sat, May 10 - Sat, May 17
Delta Logo
6:00 am - 6:34 pmMDW-LIH
17h 34m2 stops
Delta Logo
9:26 pm - 6:36 pmLIH-MDW
16h 10m2 stops
$656Delta
Find Deal
Wed, Sep 10 - Mon, Sep 15
Southwest Logo
6:05 am - 12:50 pmMDW-LIH
11h 45m1 stop
Southwest Logo
8:30 am - 11:50 pmLIH-MDW
10h 20m1 stop
$658Southwest
Find Deal
Sat, May 10 - Sat, May 17
Delta Logo
6:00 am - 7:09 pmMDW-LIH
18h 09m2 stops
Delta Logo
9:26 pm - 6:36 pmLIH-MDW
16h 10m2 stops
$676Delta
Find Deal
Thu, Oct 23 - Tue, Oct 28
Southwest Logo
5:15 am - 12:50 pmMDW-LIH
12h 35m1 stop
Southwest Logo
8:40 pm - 3:45 pmLIH-MDW
14h 05m1 stop
$678Southwest
Find Deal
Sun, Aug 24 - Tue, Sep 2
Southwest Logo
6:20 am - 2:40 pmMDW-LIH
13h 20m2 stops
Southwest Logo
8:40 pm - 3:45 pmLIH-MDW
14h 05m1 stop
$683Southwest
Find Deal
Sun, Aug 24 - Tue, Sep 2
Useful Info

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.

Which airlines provide the cheapest flights from Chicago Midway Airport to Kaua'i?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Chicago Midway Airport to Kaua'i were found on Delta ($594) and Southwest ($623).

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Good to know

Cheapest flight$332
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.

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 4294 reviews
7.1Food
8.2Boarding
8.6Crew
8.0Comfort
7.6Entertainment
Airline reviews

It is southwest seat was ok. Not the most comfortable seat

8.0 ExcellentJohn, Apr 2025PVD - FLL
Read more Southwest reviews

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

The seats were a bit cramped and worn, but otherwise okay.

I would have liked to arrive on time - not 5 hours late!

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

It was a perfect flight in all aspects! Both legs!

Only one drink pass through the cabin for a 4 hour flight. Quite rough and bumpy landing.

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

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

Information on your arrival and departure airports

Chicago Midway Airport (MDW)

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