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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 12/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
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.
Delta Logo
9:30 pm - 5:43 pmKOA-MDW
16h 13m2 stops
Delta Logo
6:00 am - 7:53 pmMDW-KOA
17h 53m2 stops
$882Delta
Find Deal
Tue, Nov 4 - Sat, Nov 8
Delta Logo
7:40 pm - 6:08 pmKOA-MDW
17h 28m2 stops
Delta Logo
9:30 am - 6:50 pmMDW-KOA
14h 20m2 stops
$4,757Delta
Find Deal
Tue, Apr 7 - Sun, Apr 12

Delta flights from Kailua-Kona to Chicago Midway Airport

Our best Delta deals on Kailua-Kona to Chicago Midway Airport flight tickets
Delta
Nov 4
KOA9:30 pmKona Intl
16h 13m
2 stops
MDW5:43 pmChicago Midway
Nov 8
MDW6:00 amChicago Midway
17h 53m
2 stops
KOA7:53 pmKona Intl
$882
Find similar
Delta
Apr 7
KOA7:40 pmKona Intl
17h 28m
2 stops
MDW6:08 pmChicago Midway
Apr 12
MDW9:30 amChicago Midway
14h 20m
2 stops
KOA6:50 pmKona Intl
$4,757
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 October 21, 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 11/4

9:30 pm-5:43 pm

2 stops16h 13m

Chicago Midway

Sat 11/8

6:00 am-7:53 pm

2 stops17h 53m

$882

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Tue 4/7

7:40 pm-6:08 pm

2 stops17h 28m

Chicago Midway

Sun 4/12

9:30 am-6:50 pm

2 stops14h 20m

$4,757

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Fri 12/5

9:30 pm-6:18 pm

2 stops16h 48m

$217

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Fri 12/5

9:00 pm-11:08 am

3 stops34h 08m

$232

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Sat 12/6

9:00 pm-2:52 pm

3 stops37h 52m

$242

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Sat 12/6

9:15 pm-4:20 pm

2 stops15h 05m

$247

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Fri 12/5

9:15 pm-11:55 am

1 stop10h 40m

$313

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Wed 3/4

6:00 am-11:20 am

3 stops49h 20m

$326

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Sat 1/31

9:45 pm-6:08 pm

2 stops16h 23m

$360

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Tue 12/2

9:30 pm-6:04 pm

3 stops40h 34m

$361

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 12 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

Direct flights

None
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.
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  • 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 16h 13m.

  • 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?

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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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