KOA - CHI

$217 Find Cheap Flights from Kailua-Kona to Chicago - Compare and Save

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Everything you should know

Cheapest round-trip
$434
Typical prices: $468-$853
Delta
Mon 10/22Sun 10/28
KOA - ORD • 1 stop
Cheapest one-way
$217
Typical prices: $312-$462
Delta
Tue 9/25
KOA - ORD • 1 stop
Nonstop flights
Not available
There are currently no direct flights between Kailua-Kona and Chicago. You'll need to take a connecting flight to reach the destination.
Insights
Insights
When to travel
January
Cheapest • 44% price drop
May
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Denver Intl (DEN)
Cheapest • Avg $486 (round-trip)
San Francisco (SFO)
Shortest trip • 10h 37m (one-way)
Insights
Insights
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Flight Deals

Cheap Flights from Kailua-Kona to Chicago (KOA-CHI)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Kailua-Kona to Chicago

Wed, Sep 9 - Sun, Sep 13
Delta Logo
8:55 pm - 6:01 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
16h 06m1 stop Seattle/Tacoma Intl
Delta Logo
7:00 am - 5:31 pmORD  Chicago O'Hare Intl-KOA Kona Intl
15h 31m1 stop Seattle/Tacoma Intl
$434Delta
Fri, Dec 4 - Mon, Dec 7
Delta Logo
10:40 pm - 4:47 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
14h 07m1 stop Seattle/Tacoma Intl
Delta Logo
6:45 am - 7:27 pmORD  Chicago O'Hare Intl-KOA Kona Intl
16h 42m1 stop Seattle/Tacoma Intl
$434Delta
Thu, Oct 22 - Wed, Oct 28
Delta Logo
9:06 pm - 4:53 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
14h 47m1 stop Seattle/Tacoma Intl
Delta Logo
6:35 am - 5:38 pmORD  Chicago O'Hare Intl-KOA Kona Intl
16h 03m1 stop Seattle/Tacoma Intl
$434Delta
Fri, Dec 4 - Mon, Dec 7
Delta Logo
8:55 pm - 5:03 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
16h 08m2 stops Salt Lake City Atlanta Hartsfield-Jackson
Delta Logo
6:45 am - 7:27 pmORD  Chicago O'Hare Intl-KOA Kona Intl
16h 42m1 stop Seattle/Tacoma Intl
$440Delta
Wed, Sep 9 - Sun, Sep 13
Delta Logo
8:55 pm - 8:30 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
18h 35m2 stops Seattle/Tacoma Intl Detroit Metropolitan Wayne County
Delta Logo
7:00 am - 5:31 pmORD  Chicago O'Hare Intl-KOA Kona Intl
15h 31m1 stop Seattle/Tacoma Intl
$440Delta
Thu, Oct 22 - Wed, Oct 28
Delta Logo
9:06 pm - 1:30 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
11h 24m1 stop Seattle/Tacoma Intl
Delta Logo
8:29 am - 7:26 pmORD  Chicago O'Hare Intl-KOA Kona Intl
15h 57m2 stops Detroit Metropolitan Wayne County Los Angeles
$440Delta
Thu, Oct 22 - Wed, Oct 28
American Airlines Logo
3:33 pm - 10:00 amKOA  Kona Intl-ORD Chicago O'Hare Intl
13h 27m2 stops Los Angeles Dallas/Fort Worth
American Airlines Logo
5:00 am - 2:03 pmORD  Chicago O'Hare Intl-KOA Kona Intl
14h 03m2 stops Dallas/Fort Worth Phoenix Sky Harbor Intl
$445American Airlines
Wed, Sep 9 - Sun, Sep 13
Delta Logo
8:55 pm - 8:30 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
18h 35m2 stops Seattle/Tacoma Intl Detroit Metropolitan Wayne County
Delta Logo
6:10 am - 5:31 pmORD  Chicago O'Hare Intl-KOA Kona Intl
16h 21m2 stops Minneapolis St Paul Seattle/Tacoma Intl
$445Delta
Fri, Dec 4 - Mon, Dec 7
Delta Logo
8:55 pm - 5:03 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
16h 08m2 stops Salt Lake City Atlanta Hartsfield-Jackson
Delta Logo
6:30 am - 6:45 pmORD  Chicago O'Hare Intl-KOA Kona Intl
16h 15m2 stops Minneapolis St Paul Los Angeles
$445Delta
Tue, Oct 20 - Fri, Oct 23
American Airlines Logo
9:45 pm - 4:09 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
13h 24m1 stop Phoenix Sky Harbor Intl
American Airlines Logo
6:48 am - 2:03 pmORD  Chicago O'Hare Intl-KOA Kona Intl
12h 15m1 stop Phoenix Sky Harbor Intl
$464American Airlines
Booking Insights

Price, demand and travel trends for Kailua-Kona to Chicago flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights from Kailua-Kona to Chicago with more confidence.

How much is a round-trip flight from Kailua-Kona to Chicago?

Round-trip flights from Kailua-Kona to Chicago start at $434. Prices are below average for this route right now, with typical round-trip fares ranging from $468 to $853. The lowest price found in the past 5 days was $434 on Delta.

What is the cheapest Kailua-Kona to Chicago flight route?

There's little price difference between Kailua-Kona to Chicago routes. They average around $653 round-trip, based on KAYAK data over the past 12 months.

What's the cheapest day of the week to fly from Kailua-Kona to Chicago?

Wednesday is the cheapest day of the week to fly from Kailua-Kona to Chicago, it is 16% cheaper than the average day. Saturday is the most expensive day with flight prices 413% higher than average. Based on deals found by KAYAK users in the last 12 months.

What is the cheapest month to fly from Kailua-Kona to Chicago?

  • January is the cheapest month to fly from Kailua-Kona to Chicago at $368 round-trip.
  • May ($1,264) and March ($1,263) are the most expensive months.
  • The price difference between flying in the cheapest and most expensive months is 243% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

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Expert advice

Expert advice for your flight from Kailua-Kona to Chicago

 
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on ORD

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Blane Bachelor

Blane Bachelor

Expert on KOA

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Read more

Key details for Kailua-Kona to Chicago flights

Low season

August

Cheapest flight

$217
Best time to beat the crowds but there is an average 4% increase in price.
Most popular time to fly with an average 94% increase in price.
Flight from Kailua-Kona to Chicago O'Hare Intl Airport

When to book flights from Kailua-Kona to Chicago

Are your dates flexible? Find out the best times to travel from Kailua-Kona to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Kailua-Kona to Chicago flight questions, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines and booking questions.

  • Which airports can I use when flying from Kailua-Kona to Chicago?

    Flights from Kailua-Kona to Chicago usually depart from Kona Intl (KOA) and may arrive at several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD).

  • What cabin classes can I book on flights from Kailua-Kona to Chicago?

    Only Economy Class is available on flights from Kailua-Kona to Chicago.

  • How much can I save by taking a layover when flying from Kailua-Kona to Chicago?

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $486 round-trip via Denver Intl (DEN), compared to $3,352 for nonstop.

  • Which airports do connecting flights from Kailua-Kona to Chicago pass through?

    One-stop flights from Kailua-Kona to Chicago most commonly connect through:

    • Los Angeles (LAX) - 29% of one-stop connections
    • Seattle/Tacoma Intl (SEA) - 25% of one-stop connections
    • Denver Intl (DEN) - 21% of one-stop connections
    • Phoenix Sky Harbor Intl (PHX) - 13% of one-stop connections

    Los Angeles (LAX) handles the largest share of one-stop connections on this route.

  • Can I save money by using flexible dates for flights from Kailua-Kona to Chicago?

    Yes. Being flexible with your travel dates can save you up to 84% on the Kailua-Kona to Chicago route. Wednesday is the cheapest departure day at $550 round-trip on average, while Saturday is the most expensive at $3,352, a difference of $2,802. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • What popular places can I visit in Chicago?

    Some of the most popular sights in Chicago are Magnificent Mile, Grant Park and River North. These are among the most viewed places in Chicago on KAYAK.

  • How long is a flight from Kailua-Kona to Chicago?

    A nonstop flight from Kailua-Kona to Chicago takes 0h 00m, covering 4,219 miles.

  • What are the earliest and latest flights from Kailua-Kona to Chicago?

    These are the earliest and latest flight times available from Kailua-Kona to Chicago:

    • Earliest: departs at 12:00 am and lands at 12:00 am
    • Latest: departs at 12:00 am and lands at 12:00 am.

    The flight takes about 0h 00m.

  • Do I need a passport to fly from Kailua-Kona to Chicago?

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID, or another TSA-accepted form of identification.

  • How are flight prices from Kailua-Kona to Chicago looking right now?

    One-way fares from Kailua-Kona to Chicago are currently higher than usual. Average one-way flight prices are about $441, which is 19% above the typical average for this route.

  • How much time can I save by choosing a different layover airport from Kailua-Kona to Chicago?

    Flying via San Francisco (SFO) gives the shortest average 1-stop total travel time at 10h 37m, compared with 10h 58m via Denver Intl (DEN) and 11h 58m via Los Angeles (LAX).

  • What is the time difference between Kailua-Kona and Chicago?

    Chicago is 5 hours ahead of Kailua-Kona (Central Time vs Hawaii-Aleutian Time). Plan for the time shift when scheduling connections or first-day activities.

  • What car rental options are available in Chicago?

    Since Chicago is served by multiple airports, car rental options and rates can vary depending on which one you fly into.
    Near Chicago O'Hare Intl Airport (ORD) — daily rates from around $17:

    · Routes Car & Truck Rentals
    · Europcar
    · Hertz
    · Dollar
    · Ace

    Near Chicago Midway Airport (MDW) — daily rates from around $32:

    · Hertz
    · Dollar
    · Budget
    · Alamo
    · Rent-A-Wreck

    Near Chicago Greater Rockford Airport (RFD) — daily rates from around $30:

    · Alamo
    · Enterprise Rent-A-Car
    · Budget
    · Avis
    · National

  • How much should I expect to pay for a Kailua-Kona to Chicago flight?

    Round-trip flights from Kailua-Kona to Chicago range from $468 to $853, with an average of $653 over the past 12 months. Anything below $468 counts as a good deal.

Your guide to booking Kailua-Kona to Chicago flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates can be flexible, aim for a Wednesday departure instead of Saturday. On this route, Wednesday flights average $550 - about $2,802 less than Saturday (84% savings) based on the last 12 months.
  • If you can choose when to travel, plan your Kailua-Kona to Chicago trip for January. Fares historically average $368 round-trip in that month - typically $896 less than the most expensive month, which is May (based on the last 12 months).
  • If you have the time, taking a 1-stop flight through Denver Intl Airport (DEN) can be cheaper than flying direct. The cheapest layover option averages $486 round-trip on this route - about $2,866 less than direct flights (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Chicago Midway Airport.
    - DoubleTree by Hilton Chicago Midway Airport
    - Holiday Inn Chicago - Midway Airport S by IHG

Everything you need to know for your flight from Kailua-Kona to Chicago

Information on your arrival and departure airports

Kailua-Kona (KOA)