$212 Cheap Flights from Chicago (MDW) to Lihue (LIH)

View $212 flight on Thu, Jan 1, 2026Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Lihue Airport (LIH)

Cheap Flights from Chicago to Lihue (MDW-LIH)

Prices were available within the past 7 days and start at $212 for one-way flights and $434 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sat, Nov 15 - Sat, Nov 22
MDW
Chicago
LIH
Kauai
$434 Roundtrip, found 4 days ago
$434
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, Nov 15 from Chicago to Kauai, returning Sat, Nov 22, priced at $434 found 4 days ago
Southwest Airlines
Tue, Oct 28 - Tue, Nov 4
MDW
Chicago
LIH
Kauai
$451 Roundtrip, found 6 days ago
$451
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Tue, Oct 28 from Chicago to Kauai, returning Tue, Nov 4, priced at $451 found 6 days ago
Southwest Airlines
Tue, Oct 28 - Tue, Nov 4
MDW
Chicago
LIH
Kauai
$456 Roundtrip, found 6 days ago
$456
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Tue, Oct 28 from Chicago to Kauai, returning Tue, Nov 4, priced at $456 found 6 days ago
Southwest Airlines
Tue, Jan 6 - Wed, Jan 21
MDW
Chicago
LIH
Kauai
$473 Roundtrip, found 5 hours ago
$473
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Tue, Jan 6 from Chicago to Kauai, returning Wed, Jan 21, priced at $473 found 5 hours ago
Southwest Airlines
Tue, Jan 6 - Wed, Jan 21
MDW
Chicago
LIH
Kauai
$479 Roundtrip, found 5 hours ago
$479
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Tue, Jan 6 from Chicago to Kauai, returning Wed, Jan 21, priced at $479 found 5 hours ago
Delta
Thu, Nov 13 - Fri, Nov 21
MDW
Chicago
LIH
Kauai
$484 Roundtrip, found 6 days ago
$484
Roundtrip
found 6 days ago
Select Delta flight, departing Thu, Nov 13 from Chicago to Kauai, returning Fri, Nov 21, priced at $484 found 6 days ago
Southwest Airlines
Sun, Nov 16 - Sat, Nov 22
MDW
Chicago
LIH
Kauai
$484 Roundtrip, found 3 days ago
$484
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Sun, Nov 16 from Chicago to Kauai, returning Sat, Nov 22, priced at $484 found 3 days ago
Southwest Airlines
Thu, Jan 1 - Wed, Jan 7
MDW
Chicago
LIH
Kauai
$485 Roundtrip, found 13 hours ago
$485
Roundtrip
found 13 hours ago
Select Southwest Airlines flight, departing Thu, Jan 1 from Chicago to Kauai, returning Wed, Jan 7, priced at $485 found 13 hours ago
Southwest Airlines
Thu, Jan 1 - Wed, Jan 7
MDW
Chicago
LIH
Kauai
$491 Roundtrip, found 13 hours ago
$491
Roundtrip
found 13 hours ago
Select Southwest Airlines flight, departing Thu, Jan 1 from Chicago to Kauai, returning Wed, Jan 7, priced at $491 found 13 hours ago
Southwest Airlines
Tue, Oct 28 - Tue, Nov 4
MDW
Chicago
LIH
Kauai
$494 Roundtrip, found 1 day ago
$494
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Tue, Oct 28 from Chicago to Kauai, returning Tue, Nov 4, priced at $494 found 1 day ago

Alternative airports near Lihue

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Lihue Airport LIH. Cheapest option available. Flights from $643
LIH
Lihue Airport
Cheapest
Flights from $643

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Lihue Airport (LIH) cost?
Secure a cheap one-way flight from $212 or cheap return flight from $434 from Midway Intl. Airport (MDW) to Lihue Airport (LIH) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Lihue Airport (LIH)?
November is the cheapest month to fly from MDW to LIH. Avoiding peak travel times is often the key to better flight prices.
How many flights per day from Midway Intl. Airport (MDW) to Lihue Airport (LIH)?
You'll have to catch a flight with a layover when traveling from Midway Intl. Airport (MDW) to Lihue Airport (LIH). Direct flights don't operate daily on this route. However, just filter your search to include one or two stops to find the best option for your trip.
What day of the week has the most flights from MDW to LIH?
Friday is typically the busiest day for flights, while Tuesday tends to be the quietest.* Keep in mind that flight schedules can change based on various factors, such as the time of year and airline.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Lihue Airport (LIH)?
Select a flight from Midway Intl. Airport (MDW) to Lihue Airport (LIH) that takes off before 3 PM to reduce the risk of delays and cancellations. Departures after this time have a 22% higher chance of being canceled, on average.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Lihue Airport (LIH) last-minute?
Holding off until just before your departure to book your flight from MDW to LIH often results in higher prices. While you may find some last-minute discounts, there's no guarantee. Keep your travel schedule open to maximize your chances of snagging a bargain.
Is it cheaper to book a MDW to LIH flight and hotel package?
Opting for a MDW to LIH flight and hotel package tends to be cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your travels all in one place. Choose from our wide range of hotels and then add flights, car rentals and activities to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Lihue Airport (LIH)?
It's usually possible to cancel or reschedule your MDW to LIH flight. However, if it's been more than 24 hours since booking, additional charges may apply. Check your airline's policies in your itinerary to see what changes are allowed and whether any costs are involved. You'll also find further details on our Customer Service portal.

Travel information

Origin airport
Midway Intl.
Destination airport
Lihue
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$433
Distance
4292 mi

Book with confidence

Chicago to Lihue Flights

The cheapest times to fly from Chicago to Lihue

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Lihue are during the month of November. You can find some of the cheapest flights from Chicago to Lihue with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Lihue

Sunday is one of the best days to book for cheap flights from Chicago to Lihue: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Lihue

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Lihue in 2025. You can also book with separate airlines for your outbound and return journeys, from $212 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Lihue flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Lihue airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Chicago to Lihue Flights

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*Available to One Key members.