$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 4/1. 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, 0 bags

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

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

Tue, Jan 20 - Tue, Feb 17
Delta Logo
9:50 am - 7:55 pm
MDW
-
LIH
14h 05m2 stops
Delta Logo
10:55 pm - 5:37 pm
LIH
-
MDW
14h 42m2 stops
$414Delta
Tue, Feb 3 - Mon, Feb 9
Delta Logo
9:33 am - 7:54 pm
MDW
-
LIH
14h 21m2 stops
Delta Logo
10:35 pm - 5:55 pm
LIH
-
MDW
15h 20m2 stops
$434Delta
Tue, Feb 24 - Wed, Mar 4
Delta Logo
9:34 am - 7:55 pm
MDW
-
LIH
14h 21m2 stops
Delta Logo
9:45 pm - 5:37 pm
LIH
-
MDW
15h 52m2 stops
$444Delta
Tue, Feb 24 - Wed, Mar 4
Delta Logo
9:34 am - 7:55 pm
MDW
-
LIH
14h 21m2 stops
Delta Logo
9:45 pm - 5:37 pm
LIH
-
MDW
15h 52m2 stops
$454Delta
Wed, Feb 4 - Mon, Feb 9
Delta Logo
9:32 am - 7:54 pm
MDW
-
LIH
14h 22m2 stops
Delta Logo
10:35 pm - 5:55 pm
LIH
-
MDW
15h 20m2 stops
$494Delta
Tue, Feb 24 - Tue, Mar 10
Delta Logo
9:34 am - 7:55 pm
MDW
-
LIH
14h 21m2 stops
Delta Logo
8:30 pm - 6:40 pm
LIH
-
MDW
17h 10m2 stops
$505Delta
Wed, Feb 25 - Tue, Mar 3
Delta Logo
9:50 am - 7:55 pm
MDW
-
LIH
14h 05m2 stops
Delta Logo
9:45 pm - 5:37 pm
LIH
-
MDW
15h 52m2 stops
$514Delta
Tue, Feb 24 - Tue, Mar 10
Delta Logo
9:34 am - 7:55 pm
MDW
-
LIH
14h 21m2 stops
Delta Logo
8:30 pm - 6:40 pm
LIH
-
MDW
17h 10m2 stops
$515Delta
Tue, Feb 24 - Tue, Mar 10
Delta Logo
9:34 am - 7:55 pm
MDW
-
LIH
14h 21m2 stops
Delta Logo
9:40 pm - 5:55 pm
LIH
-
MDW
15h 15m2 stops
$524Delta
Tue, Feb 3 - Mon, Feb 9
Southwest Logo
5:05 am - 2:25 pm
MDW
-
LIH
13h 20m2 stops
Southwest Logo
9:15 pm - 12:35 pm
LIH
-
MDW
11h 20m1 stop
$529Southwest
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 $398, 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.
7.9
SouthwestOverall score based on 4250 reviews
7.5Entertainment
7.0Food
8.6Crew
8.0Comfort
8.1Boarding
Airline reviews

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

2.0 MediocreRobert, Dec 2025
LAS - TPA
Read more Southwest reviews

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

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

Information on your arrival and departure airports