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Cheap flights from Kailua-Kona to Chicago from $217

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Kailua-Kona to Chicago departing on 1/29. 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 Kailua-Kona to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
9:15 pm - 11:35 am
KOA
-
MDW
10h 20m1 stop
Southwest Logo
5:10 am - 1:40 pm
MDW
-
KOA
12h 30m1 stop
$998Southwest
Wed, Dec 24 - Mon, Dec 29
Southwest Logo
6:55 pm - 12:45 pm
KOA
-
MDW
13h 50m2 stops
Southwest Logo
5:10 am - 1:40 pm
MDW
-
KOA
12h 30m1 stop
$1,003Southwest
Wed, Dec 24 - Mon, Dec 29
Southwest Logo
9:15 pm - 3:00 pm
KOA
-
MDW
13h 45m2 stops
Southwest Logo
5:10 am - 6:10 pm
MDW
-
KOA
17h 00m2 stops
$1,044Southwest
Wed, Dec 24 - Mon, Dec 29
Delta Logo
9:30 pm - 5:37 pm
KOA
-
MDW
16h 07m2 stops
Delta Logo
6:45 am - 6:30 pm
MDW
-
KOA
15h 45m2 stops
$1,336Delta
Thu, Jan 8 - Thu, Jan 15

Southwest flights from Kailua-Kona to Chicago Midway Airport

Our best Southwest deals on Kailua-Kona to Chicago Midway Airport flight tickets
Southwest
Dec 20
KOA9:15 pmKona Intl
11h 00m
1 stop
MDW12:15 pmChicago Midway
Jan 10
MDW8:20 amChicago Midway
13h 50m
2 stops
KOA6:10 pmKona Intl
$732
Find similar
Southwest
Dec 20
KOA9:15 pmKona Intl
14h 20m
2 stops
MDW3:35 pmChicago Midway
Jan 10
MDW8:20 amChicago Midway
13h 50m
2 stops
KOA6:10 pmKona Intl
$759
Find similar
Southwest
Dec 20
KOA9:15 pmKona Intl
11h 00m
1 stop
MDW12:15 pmChicago Midway
Jan 10
MDW5:35 amChicago Midway
12h 15m
1 stop
KOA1:50 pmKona Intl
$817
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Kailua-Kona 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 December 11, 2025.
Use the filters below to find and compare flights from Kailua-Kona to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Wed 12/24

9:15 pm-11:35 am

1 stop10h 20m

Chicago Midway

Mon 12/29

5:10 am-1:40 pm

1 stop12h 30m

$998

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Wed 12/24

6:55 pm-12:45 pm

2 stops13h 50m

Chicago Midway

Mon 12/29

5:10 am-1:40 pm

1 stop12h 30m

$1,003

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Wed 12/24

9:15 pm-3:00 pm

2 stops13h 45m

Chicago Midway

Mon 12/29

5:10 am-6:10 pm

2 stops17h 00m

$1,044

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Thu 1/8

9:30 pm-5:37 pm

2 stops16h 07m

Chicago Midway

Thu 1/15

6:45 am-6:30 pm

2 stops15h 45m

$1,336

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Thu 1/29

7:55 pm-12:46 pm

2 stops12h 51m

$217

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Thu 1/29

7:00 pm-12:35 pm

2 stops13h 35m

$245

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Fri 1/30

8:45 pm-4:16 pm

2 stops15h 31m

$249

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Wed 1/21

1:43 pm-3:49 pm

3 stops46h 06m

$253

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Wed 1/28

7:40 pm-3:49 pm

3 stops40h 09m

$254

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Fri 1/30

7:40 pm-11:13 pm

3 stops47h 33m

$276

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 14 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Kailua-Kona 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 Kona Intl to Chicago Midway?

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

When to book flights from Kailua-Kona to Chicago Midway Airport

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

Cheap Kailua-Kona to Chicago Midway Airport (KOA to MDW) flight deals and tips

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

Fastest flight time

11h 00m

Direct flights

None
The fastest flight from Kailua-Kona to Chicago Midway Airport takes 11h 00m
There are no direct flights from Kailua-Kona to Chicago Midway Airport. There are no popular flight routes from Kailua-Kona to Chicago Midway Airport.
Search flight deals

  • How far is Kona Intl to Chicago Midway by plane?

    Chicago Midway is 4214.3 mi away from Kona Intl. By plane, this route typically takes 11h 00m.

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

    Prices for flights from Kona Intl Airport to Chicago Midway Airport were last updated today.

  • How old do you have to be to fly from Kona Intl Airport to Chicago Midway Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Kona Intl Airport to Chicago Midway Airport.

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

    The required travel and health documents for your Chicago Midway Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago Midway Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Kailua-Kona to Chicago?

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

Can I find flights from Kailua-Kona to Chicago with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Kailua-Kona to Chicago flights to just show those with flexible booking policies.

How can momondo help me find flights from Kailua-Kona to Chicago?

momondo provides multiple filters to help you find the best flight to Chicago from Kailua-Kona. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

If you are not ready to book a flight from Kailua-Kona to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

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