$205 Cheap Flights from Lihue (LIH) to Chicago (MDW)

View $205 flight on Tue, Sep 9, 2025Opens in a new window

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

Cheap Flights from Lihue to Chicago (LIH-MDW)

Prices were available within the past 7 days and start at $205 for one-way flights and $479 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Tue, Nov 11 - Tue, Nov 18
LIH
Kauai
MDW
Chicago
$479 Roundtrip, found 5 days ago
$479
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Tue, Nov 11 from Kauai to Chicago, returning Tue, Nov 18, priced at $479 found 5 days ago
Southwest Airlines
Tue, Nov 11 - Tue, Nov 18
LIH
Kauai
MDW
Chicago
$484 Roundtrip, found 5 days ago
$484
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Tue, Nov 11 from Kauai to Chicago, returning Tue, Nov 18, priced at $484 found 5 days ago
Southwest Airlines
Mon, Jan 12 - Thu, Jan 22
LIH
Kauai
MDW
Chicago
$568 Roundtrip, found 5 days ago
$568
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Mon, Jan 12 from Kauai to Chicago, returning Thu, Jan 22, priced at $568 found 5 days ago
Southwest Airlines
Tue, Nov 11 - Tue, Nov 18
LIH
Kauai
MDW
Chicago
$569 Roundtrip, found 5 days ago
$569
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Tue, Nov 11 from Kauai to Chicago, returning Tue, Nov 18, priced at $569 found 5 days ago
Southwest Airlines
Sat, Nov 22 - Sat, Nov 29
LIH
Kauai
MDW
Chicago
$574 Roundtrip, found 6 days ago
$574
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Sat, Nov 22 from Kauai to Chicago, returning Sat, Nov 29, priced at $574 found 6 days ago
Southwest Airlines
Tue, Nov 11 - Tue, Nov 18
LIH
Kauai
MDW
Chicago
$575 Roundtrip, found 5 days ago
$575
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Tue, Nov 11 from Kauai to Chicago, returning Tue, Nov 18, priced at $575 found 5 days ago
Southwest Airlines
Mon, Jan 12 - Thu, Jan 22
LIH
Kauai
MDW
Chicago
$588 Roundtrip, found 5 days ago
$588
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Mon, Jan 12 from Kauai to Chicago, returning Thu, Jan 22, priced at $588 found 5 days ago
Southwest Airlines
Sat, Nov 22 - Sat, Nov 29
LIH
Kauai
MDW
Chicago
$594 Roundtrip, found 6 days ago
$594
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Sat, Nov 22 from Kauai to Chicago, returning Sat, Nov 29, priced at $594 found 6 days ago
Southwest Airlines
Sat, Nov 22 - Sat, Nov 29
LIH
Kauai
MDW
Chicago
$599 Roundtrip, found 6 days ago
$599
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Sat, Nov 22 from Kauai to Chicago, returning Sat, Nov 29, priced at $599 found 6 days ago
Delta
Thu, Feb 19 - Wed, Feb 25
LIH
Kauai
MDW
Chicago
$1,021 Roundtrip, just found
$1,021
Roundtrip
just found
Select Delta flight, departing Thu, Feb 19 from Kauai to Chicago, returning Wed, Feb 25, priced at $1,021 just found

Alternative airports near Chicago

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

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $479
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $479
Flights from Lihue (LIH) to Chicago (MDW)
Origin airport
Lihue
Destination airport
Midway Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$479
Distance
4292 mi

Lihue to Chicago Flights

The cheapest times to fly from Lihue to Chicago

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 Lihue to Chicago are during the month of November. You can find some of the cheapest flights from Lihue to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Lihue to Chicago

Sunday is one of the best days to book for cheap flights from Lihue to Chicago: 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 Lihue to Chicago

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 Lihue to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $205 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 Lihue to Chicago 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 Lihue to Chicago 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.

 

Frequently asked questions

How much does a flight from Lihue Airport (LIH) to Midway Intl. Airport (MDW) cost?
Lock in a cheap one-way flight from $205 or cheap return flight from $479 from Lihue Airport (LIH) to Midway Intl. Airport (MDW) 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 Lihue Airport (LIH) to Midway Intl. Airport (MDW)?
November is the most affordable month to fly from LIH to MDW. Planning your trip for the off-season is often the key to finding a great deal.
What is the cheapest airline that flies from Lihue Airport (LIH) to Midway Intl. Airport (MDW)?
To find the cheapest airline flying from LIH to MDW, use Expedia's filter tool. Customize your search based on what's important to you, such as preferred carriers and number of stops. You can then sort your results by "Price (lowest to highest)" to list the most affordable options first.
How many flights per day from Lihue Airport (LIH) to Midway Intl. Airport (MDW)?
There are no daily nonstop flights departing from Lihue Airport (LIH) to Midway Intl. Airport (MDW). But you can choose flights with layovers. Filter your search results on Expedia to include one or two stops, and you'll be cruising above the clouds in no time.
What day of the week has the most flights from LIH to MDW?
You'll typically find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can change from season to season and during public holidays or peak travel times.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Lihue Airport (LIH) to Midway Intl. Airport (MDW)?
To land at Midway Intl. Airport (MDW) on schedule, book a flight that leaves from Lihue Airport (LIH) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this time.**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 Lihue Airport (LIH) to Midway Intl. Airport (MDW) last-minute?
Last-minute fares from LIH to MDW are typically more expensive. For the cheapest rates, start looking for flights well ahead of time. That said, if you're flexible with your travel dates, you may score a cheap fare right before your trip.
Is it cheaper to book a LIH to MDW flight and hotel package?
Compared with arranging hotels and flights separately, booking a LIH to MDW flight and hotel package with Expedia could lead to significant savings. Better yet, having it all in one place takes the hassle out of planning your trip. Just pick your flights and choose from our wide range of stays, then customize your trip with other add-ons like activities, tours and car rentals.
Can I cancel or change the date of my flight from Lihue Airport (LIH) to Midway Intl. Airport (MDW)?
If you booked your LIH to MDW flight in the last 24 hours, you may be able to cancel or modify it at no cost. Depending on the airline and the type of fare you purchased, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal if you'd like more information.

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*Available to One Key members.