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Cheap flights from Lihue to Chicago from $357

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Lihue to Chicago departing on 6/16. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Lihue to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
8:10 pm - 12:00 pm
LIH
-
MDW
10h 50m
1 stop
Southwest Logo
7:30 am - 4:10 pm
MDW
-
LIH
13h 40m
2 stops
$786Southwest
Mon, Jun 1 - Fri, Jun 5
Southwest Logo
8:10 pm - 12:00 pm
LIH
-
MDW
10h 50m
1 stop
Southwest Logo
9:35 pm - 10:00 am
MDW
-
LIH
17h 25m
1 stop
$790Southwest
Mon, Jun 1 - Fri, Jun 5
Southwest Logo
6:15 am - 11:55 pm
LIH
-
MDW
12h 40m
2 stops
Southwest Logo
7:30 am - 4:10 pm
MDW
-
LIH
13h 40m
2 stops
$805Southwest
Mon, Jun 1 - Fri, Jun 5
Southwest Logo
11:20 am - 5:55 am
LIH
-
MDW
13h 35m
1 stop
Southwest Logo
10:00 am - 4:10 pm
MDW
-
LIH
11h 10m
1 stop
$931Southwest
Sun, Jul 12 - Sun, Jul 19
Southwest Logo
6:15 am - 11:25 pm
LIH
-
MDW
12h 10m
2 stops
Southwest Logo
5:00 am - 2:15 pm
MDW
-
LIH
14h 15m
2 stops
$942Southwest
Mon, Jun 15 - Sun, Jun 21
Southwest Logo
11:20 am - 5:55 am
LIH
-
MDW
13h 35m
1 stop
Southwest Logo
10:00 am - 4:10 pm
MDW
-
LIH
11h 10m
1 stop
$956Southwest
Sun, Jul 12 - Sun, Jul 19
Southwest Logo
7:10 pm - 1:55 pm
LIH
-
MDW
13h 45m
2 stops
Southwest Logo
10:00 am - 4:10 pm
MDW
-
LIH
11h 10m
1 stop
$982Southwest
Sun, Jul 12 - Sun, Jul 19
Southwest Logo
8:10 pm - 11:20 am
LIH
-
MDW
10h 10m
1 stop
Southwest Logo
10:00 am - 4:10 pm
MDW
-
LIH
11h 10m
1 stop
$1,161Southwest
Mon, Jun 15 - Sun, Jun 21
Southwest Logo
7:10 pm - 3:15 pm
LIH
-
MDW
15h 05m
2 stops
Southwest Logo
5:25 am - 2:15 pm
MDW
-
LIH
13h 50m
2 stops
$1,172Southwest
Sun, Jul 12 - Sun, Jul 19

Southwest flights from Lihue to Chicago Midway Airport

Our best Southwest deals on Lihue to Chicago Midway Airport flight tickets
Southwest
Jun 1
LIH8:10 pmLihue
10h 50m
1 stop
MDW12:00 pmChicago Midway
Jun 5
MDW7:30 amChicago Midway
13h 40m
2 stops
LIH4:10 pmLihue
$786
Southwest
Jun 1
LIH8:10 pmLihue
10h 50m
1 stop
MDW12:00 pmChicago Midway
Jun 5
MDW9:35 pmChicago Midway
17h 25m
1 stop
LIH10:00 amLihue
$790
Southwest
Jun 1
LIH6:15 amLihue
12h 40m
2 stops
MDW11:55 pmChicago Midway
Jun 5
MDW7:30 amChicago Midway
13h 40m
2 stops
LIH4:10 pmLihue
$805

momondo Fare Finder

 
Customize your flight search to find flights from Lihue to Chicago Midway Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated May 23, 2026.
Use the filters below to find and compare flights from Lihue to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

LihueChicago

LIH - MDW

LIHMDW

Lihue

Mon 6/1

8:10 pm-12:00 pm

1 stop10h 50m

Chicago Midway

Fri 6/5

7:30 am-4:10 pm

2 stops13h 40m

$786

LihueChicago

LIH - MDW

LIHMDW

Lihue

Mon 6/1

8:10 pm-12:00 pm

1 stop10h 50m

Chicago Midway

Fri 6/5

9:35 pm-10:00 am

1 stop17h 25m

$790

LihueChicago

LIH - MDW

LIHMDW

Lihue

Mon 6/1

6:15 am-11:55 pm

2 stops12h 40m

Chicago Midway

Fri 6/5

7:30 am-4:10 pm

2 stops13h 40m

$805

LihueChicago

LIH - MDW

LIHMDW

Lihue

Sun 7/12

11:20 am-5:55 am

1 stop13h 35m

Chicago Midway

Sun 7/19

10:00 am-4:10 pm

1 stop11h 10m

$931

LihueChicago

LIH - MDW

LIHMDW

Lihue

Mon 6/15

6:15 am-11:25 pm

2 stops12h 10m

Chicago Midway

Sun 6/21

5:00 am-2:15 pm

2 stops14h 15m

$942

LihueChicago

LIH - MDW

LIHMDW

Lihue

Sun 7/12

11:20 am-5:55 am

1 stop13h 35m

Chicago Midway

Sun 7/19

10:00 am-4:10 pm

1 stop11h 10m

$956

LihueChicago

LIH - MDW

LIHMDW

Lihue

Sun 7/12

7:10 pm-1:55 pm

2 stops13h 45m

Chicago Midway

Sun 7/19

10:00 am-4:10 pm

1 stop11h 10m

$982
Quickest round-trip

LihueChicago

LIH - MDW

LIHMDW

Lihue

Mon 6/15

8:10 pm-11:20 am

1 stop10h 10m

Chicago Midway

Sun 6/21

10:00 am-4:10 pm

1 stop11h 10m

$1,161

LihueChicago

LIH - MDW

LIHMDW

Lihue

Sun 7/12

7:10 pm-3:15 pm

2 stops15h 05m

Chicago Midway

Sun 7/19

5:25 am-2:15 pm

2 stops13h 50m

$1,172
Cheapest one-way
Quickest one-way

LihueChicago

LIH - MDW

LIHMDW

Lihue

Tue 6/16

8:10 pm-11:20 am

1 stop10h 10m

$357

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 19 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Lihue 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

What is the cheapest airline that flies from Lihue to Chicago Midway?

Southwest and Delta are the most popular carriers operating from Lihue to Chicago Midway

When to book flights from Lihue to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Lihue to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Lihue to Chicago Midway Airport (LIH to MDW) flight deals and tips

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

Fastest flight time

13h 35m

Direct flights

None
The fastest flight from Lihue to Chicago Midway Airport takes 13h 35m
There are no direct flights from Lihue to Chicago Midway Airport. There are no popular flight routes from Lihue to Chicago Midway Airport.
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Frequently asked questions about flying from Lihue to Chicago Midway Airport

  • How far is Lihue to Chicago Midway by plane?

    There are 4290.2 mi between Lihue and Chicago Midway. In terms of flight time, this usually takes a little over 13h 35m.

  • When did momondo last update prices for flights from Lihue Airport to Chicago Midway Airport?

    Prices for flights from Lihue Airport to Chicago Midway Airport are updated daily.

  • How old do you have to be to fly from Lihue Airport 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 Lihue Airport to Chicago Midway Airport.

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

    The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Hammond
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Benton Harbor
Portage
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Munster
Schererville
Crown Point
Chesterton
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Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Lihue to Chicago?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Lihue to Chicago. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Lihue to Chicago with flexible booking policies on momondo?

Flights from Lihue 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 Lihue 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 Lihue to Chicago.

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

Yes momondo offers price alerts on flights to Chicago from Lihue. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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