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Cheap flights from Kailua-Kona to Chicago from $377

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 1/9. 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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Find the cheapest flights from Kailua-Kona to Chicago

Cheap round-trip flights

Southwest Logo
8:30 pm - 11:45 amKOA-MDW
10h 15m1 stop
Southwest Logo
6:10 am - 12:10 pmMDW-KOA
11h 00m1 stop
$577Southwest
Find Deal
Tue, Sep 2 - Tue, Sep 9
Southwest Logo
8:30 pm - 11:45 amKOA-MDW
10h 15m1 stop
Southwest Logo
6:10 am - 6:10 pmMDW-KOA
17h 00m2 stops
$582Southwest
Find Deal
Tue, Sep 2 - Tue, Sep 9
Delta Logo
8:41 pm - 6:37 pmKOA-MDW
16h 56m2 stops
Delta Logo
6:00 am - 7:00 pmMDW-KOA
18h 00m2 stops
$602Delta
Find Deal
Tue, Sep 2 - Tue, Sep 9
Southwest Logo
8:30 pm - 11:45 amKOA-MDW
10h 15m1 stop
Southwest Logo
5:15 am - 12:10 pmMDW-KOA
11h 55m1 stop
$609Southwest
Find Deal
Tue, Sep 16 - Mon, Sep 29
Southwest Logo
8:30 pm - 1:55 pmKOA-MDW
12h 25m2 stops
Southwest Logo
5:15 am - 12:10 pmMDW-KOA
11h 55m1 stop
$614Southwest
Find Deal
Tue, Sep 16 - Mon, Sep 29
Southwest Logo
9:15 am - 5:10 amKOA-MDW
14h 55m2 stops
Southwest Logo
5:15 am - 1:05 pmMDW-KOA
12h 50m2 stops
$620Southwest
Find Deal
Tue, Sep 16 - Mon, Sep 29
Southwest Logo
8:30 pm - 2:30 pmKOA-MDW
13h 00m1 stop
Southwest Logo
6:10 am - 12:10 pmMDW-KOA
11h 00m1 stop
$631Southwest
Find Deal
Thu, Sep 18 - Wed, Oct 1
Southwest Logo
8:30 pm - 2:40 pmKOA-MDW
13h 10m2 stops
Southwest Logo
6:10 am - 12:10 pmMDW-KOA
11h 00m1 stop
$636Southwest
Find Deal
Thu, Sep 18 - Wed, Oct 1
Delta Logo
8:30 pm - 5:43 pmKOA-MDW
16h 13m2 stops
Delta Logo
9:35 am - 7:23 pmMDW-KOA
14h 48m2 stops
$684Delta
Find Deal
Tue, Oct 7 - Tue, Oct 14
Southwest Logo
8:30 pm - 11:45 amKOA-MDW
10h 15m1 stop
Southwest Logo
7:45 am - 6:10 pmMDW-KOA
15h 25m2 stops
$733Southwest
Find Deal
Thu, Sep 18 - Thu, Oct 2

Southwest flights from Kailua-Kona to Chicago Midway Airport

Our best Southwest deals on Kailua-Kona to Chicago Midway Airport flight tickets
Southwest
Sep 2
KOA8:30 pmKona Intl
10h 15m
1 stop
MDW11:45 amChicago Midway
Sep 9
MDW6:10 amChicago Midway
11h 00m
1 stop
KOA12:10 pmKona Intl
$577
Find similar
Southwest
Sep 2
KOA8:30 pmKona Intl
10h 15m
1 stop
MDW11:45 amChicago Midway
Sep 9
MDW6:10 amChicago Midway
17h 00m
2 stops
KOA6:10 pmKona Intl
$582
Find similar
Southwest
Sep 16
KOA8:30 pmKona Intl
10h 15m
1 stop
MDW11:45 amChicago Midway
Sep 29
MDW5:15 amChicago Midway
11h 55m
1 stop
KOA12:10 pmKona Intl
$609
Find similar

Delta flights from Kailua-Kona to Chicago Midway Airport

Our best Delta deals on Kailua-Kona to Chicago Midway Airport flight tickets
Delta
Sep 2
KOA8:41 pmKona Intl
16h 56m
2 stops
MDW6:37 pmChicago Midway
Sep 9
MDW6:00 amChicago Midway
18h 00m
2 stops
KOA7:00 pmKona Intl
$602
Find similar
Delta
Oct 7
KOA8:30 pmKona Intl
16h 13m
2 stops
MDW5:43 pmChicago Midway
Oct 14
MDW9:35 amChicago Midway
14h 48m
2 stops
KOA7:23 pmKona Intl
$684
Find similar
Delta
Aug 18
KOA8:41 pmKona Intl
15h 56m
2 stops
MDW5:37 pmChicago Midway
Aug 22
MDW9:15 amChicago Midway
14h 45m
2 stops
KOA7:00 pmKona Intl
$963
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 August 4, 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

Tue 9/2

8:30 pm-11:45 am

1 stop10h 15m

Chicago Midway

Tue 9/9

6:10 am-12:10 pm

1 stop11h 00m

$577

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Tue 9/2

8:30 pm-11:45 am

1 stop10h 15m

Chicago Midway

Tue 9/9

6:10 am-6:10 pm

2 stops17h 00m

$582

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Tue 9/2

8:41 pm-6:37 pm

2 stops16h 56m

Chicago Midway

Tue 9/9

6:00 am-7:00 pm

2 stops18h 00m

$602

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Tue 9/16

8:30 pm-11:45 am

1 stop10h 15m

Chicago Midway

Mon 9/29

5:15 am-12:10 pm

1 stop11h 55m

$609

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Tue 9/16

8:30 pm-1:55 pm

2 stops12h 25m

Chicago Midway

Mon 9/29

5:15 am-12:10 pm

1 stop11h 55m

$614

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Tue 9/16

9:15 am-5:10 am

2 stops14h 55m

Chicago Midway

Mon 9/29

5:15 am-1:05 pm

2 stops12h 50m

$620

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Thu 9/18

8:30 pm-2:30 pm

1 stop13h 00m

Chicago Midway

Wed 10/1

6:10 am-12:10 pm

1 stop11h 00m

$631

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Thu 9/18

8:30 pm-2:40 pm

2 stops13h 10m

Chicago Midway

Wed 10/1

6:10 am-12:10 pm

1 stop11h 00m

$636

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Tue 10/7

8:30 pm-5:43 pm

2 stops16h 13m

Chicago Midway

Tue 10/14

9:35 am-7:23 pm

2 stops14h 48m

$684

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Thu 9/18

8:30 pm-11:45 am

1 stop10h 15m

Chicago Midway

Thu 10/2

7:45 am-6:10 pm

2 stops15h 25m

$733

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 17 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

Best Price Found

$377

Fastest flight time

10h 15m

Direct flights

None
The best one-way flight to Chicago Midway Airport from Kailua-Kona in the past 72 hours is $377. The best round-trip flight deal from Kailua-Kona to Chicago Midway Airport found on momondo in the last 72 hours is $577.
The fastest flight from Kailua-Kona to Chicago Midway Airport takes 10h 15m
There are no direct flights from Kailua-Kona to Chicago Midway Airport. Popular non-direct route for this connection is Kona Intl Airport - 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 10h 15m.

  • 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
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Valparaiso
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Munster
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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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