What is the cheapest airline that flies from Kaua'i to Chicago Midway?

Delta and Southwest are the most popular carriers operating from Kaua'i to Chicago Midway

When did momondo last update prices for flights from Kaua'i to Chicago Midway Airport?

Prices for flights from Kaua'i to Chicago Midway Airport are refreshed on a daily basis.

How old do you have to be to fly from Kaua'i to Chicago Midway Airport?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Kaua'i to Chicago Midway Airport.

What documentation or ID do you need to fly to Chicago Midway Airport?

The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$223 Cheap Flights from Kaua'i to Chicago Midway Airport in 2026

1 adult

0 bags

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Find the cheapest flights from Kaua'i to Chicago

Round-trip

One-way

Cheap round-trip flights

Enter your travel dates to find the best prices.

8:10 pm - 1:45 pm

LIH

MDW

12h 35m

2 stops

6:10 am - 2:15 pm

MDW

LIH

13h 05m

2 stops

$632Southwest

Tue, Mar 31 - Tue, Apr 7

8:10 pm - 1:35 pm

LIH

MDW

12h 25m

1 stop

5:00 am - 1:10 pm

MDW

LIH

13h 10m

1 stop

$658Southwest

Sun, Mar 15 - Thu, Mar 19

8:10 pm - 2:50 pm

LIH

MDW

13h 40m

1 stop

6:10 am - 2:15 pm

MDW

LIH

13h 05m

2 stops

$661Southwest

Tue, Mar 31 - Tue, Apr 7

8:10 pm - 1:35 pm

LIH

MDW

12h 25m

1 stop

5:00 am - 2:15 pm

MDW

LIH

14h 15m

2 stops

$685Southwest

Sun, Mar 15 - Thu, Mar 19

8:10 pm - 2:50 pm

LIH

MDW

13h 40m

1 stop

10:00 am - 4:10 pm

MDW

LIH

11h 10m

1 stop

$708Southwest

Tue, Mar 31 - Tue, Apr 7

9:10 pm - 6:05 pm

LIH

MDW

15h 55m

2 stops

7:15 am - 4:10 pm

MDW

LIH

13h 55m

2 stops

$725Southwest

Sun, Mar 15 - Thu, Mar 19

8:31 pm - 6:33 pm

LIH

MDW

17h 02m

2 stops

9:23 am - 5:40 pm

MDW

LIH

13h 17m

2 stops

$875Delta

Fri, May 22 - Sun, May 31

8:31 pm - 6:33 pm

LIH

MDW

17h 02m

2 stops

9:22 am - 7:06 pm

MDW

LIH

14h 44m

2 stops

$895Delta

Fri, May 22 - Sun, May 31

8:31 pm - 6:33 pm

LIH

MDW

17h 02m

2 stops

9:23 am - 5:40 pm

MDW

LIH

13h 17m

2 stops

$935Delta

Fri, May 22 - Sun, May 31

Southwest flights from Kaua'i to Chicago Midway Airport

Our best Southwest deals on Kaua'i to Chicago Midway Airport flight tickets

Southwest

Mar 31

LIH8:10 pmLihue

12h 35m

2 stops

MDW1:45 pmChicago Midway

Apr 7

MDW6:10 amChicago Midway

13h 05m

2 stops

LIH2:15 pmLihue

$632

Southwest

Mar 15

LIH8:10 pmLihue

12h 25m

1 stop

MDW1:35 pmChicago Midway

Mar 19

MDW5:00 amChicago Midway

13h 10m

1 stop

LIH1:10 pmLihue

$658

Southwest

Mar 31

LIH8:10 pmLihue

13h 40m

1 stop

MDW2:50 pmChicago Midway

Apr 7

MDW6:10 amChicago Midway

13h 05m

2 stops

LIH2:15 pmLihue

$661

Delta flights from Kaua'i to Chicago Midway Airport

Our best Delta deals on Kaua'i to Chicago Midway Airport flight tickets

Delta

May 22

LIH8:31 pmLihue

17h 02m

2 stops

MDW6:33 pmChicago Midway

May 31

MDW9:23 amChicago Midway

13h 17m

2 stops

LIH5:40 pmLihue

$875

Delta

May 22

LIH8:31 pmLihue

17h 02m

2 stops

MDW6:33 pmChicago Midway

May 31

MDW9:22 amChicago Midway

14h 44m

2 stops

LIH7:06 pmLihue

$895

Delta

May 22

LIH8:31 pmLihue

17h 02m

2 stops

MDW6:33 pmChicago Midway

May 31

MDW9:23 amChicago Midway

13h 17m

2 stops

LIH5:40 pmLihue

$935

momondo Fare Finder

Use the filters below to find and compare flights from Kaua'i to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

LihueChicago

LIH - MDW

LIHMDW

Lihue

Tue 3/31

8:10 pm-1:45 pm

2 stops12h 35m

Chicago Midway

Tue 4/7

6:10 am-2:15 pm

2 stops13h 05m

$632

LihueChicago

LIH - MDW

LIHMDW

Lihue

Sun 3/15

8:10 pm-1:35 pm

1 stop12h 25m

Chicago Midway

Thu 3/19

5:00 am-1:10 pm

1 stop13h 10m

$658

LihueChicago

LIH - MDW

LIHMDW

Lihue

Tue 3/31

8:10 pm-2:50 pm

1 stop13h 40m

Chicago Midway

Tue 4/7

6:10 am-2:15 pm

2 stops13h 05m

$661

LihueChicago

LIH - MDW

LIHMDW

Lihue

Sun 3/15

8:10 pm-1:35 pm

1 stop12h 25m

Chicago Midway

Thu 3/19

5:00 am-2:15 pm

2 stops14h 15m

$685

LihueChicago

LIH - MDW

LIHMDW

Lihue

Tue 3/31

8:10 pm-2:50 pm

1 stop13h 40m

Chicago Midway

Tue 4/7

10:00 am-4:10 pm

1 stop11h 10m

$708

LihueChicago

LIH - MDW

LIHMDW

Lihue

Sun 3/15

9:10 pm-6:05 pm

2 stops15h 55m

Chicago Midway

Thu 3/19

7:15 am-4:10 pm

2 stops13h 55m

$725

LihueChicago

LIH - MDW

LIHMDW

Lihue

Fri 5/22

8:31 pm-6:33 pm

2 stops17h 02m

Chicago Midway

Sun 5/31

9:23 am-5:40 pm

2 stops13h 17m

$875

LihueChicago

LIH - MDW

LIHMDW

Lihue

Fri 5/22

8:31 pm-6:33 pm

2 stops17h 02m

Chicago Midway

Sun 5/31

9:22 am-7:06 pm

2 stops14h 44m

$895

LihueChicago

LIH - MDW

LIHMDW

Lihue

Fri 5/22

8:31 pm-6:33 pm

2 stops17h 02m

Chicago Midway

Sun 5/31

9:23 am-5:40 pm

2 stops13h 17m

$935

LihueChicago

LIH - MDW

LIHMDW

Lihue

Fri 5/1

8:20 pm-5:58 pm

2 stops16h 38m

$223

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 19 resultsSorted by cheapest first

How to get the cheapest flight ticket from Kaua'i to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Can stopping save me money on Kaua'i to Chicago Midway Airport flights?

No. A direct flight is the cheapest option for a flight between Kaua'i to Chicago Midway Airport.

Cheap Kaua'i to Chicago Midway Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Kaua'i to Chicago Midway Airport

Fastest flight time	12h 35m
Direct flights	None

The fastest flight from Kaua'i to Chicago Midway Airport takes 12h 35m

There are no direct flights from Kaua'i to Chicago Midway Airport. There are no popular flight routes from Kaua'i to Chicago Midway Airport.

Search flight deals

When did momondo last update prices for flights from Kaua'i to Chicago Midway Airport?
Prices for flights from Kaua'i to Chicago Midway Airport are refreshed on a daily basis.
How old do you have to be to fly from Kaua'i to Chicago Midway Airport?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Kaua'i to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Kaua'i to Chicago Midway Airport?
Based on momondo bookings for flights between Kaua'i and Chicago Midway Airport, the leading plane model is Boeing 737 MAX 8, making up 16.46% of the total bookings. Other popular models include Boeing 737-800 with 10.71%, Boeing 737-800 Passenger/BBJ2 (winglets) with 10.50%, and Airbus A321neo with 8.36%.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Valparaiso

Schererville

Munster

Crown Point

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Kaua'i to Chicago?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Kaua'i.

Can I find flights from Kaua'i to Chicago with flexible booking policies on momondo?

Flights from Kaua'i to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Kaua'i to Chicago?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Kaua'i to Chicago.

I’m not ready to book a flight from Kaua'i to Chicago right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Kaua'i and alert you when they change.