CHI - KOA

$289 Find Cheap Flights from Chicago to Kailua-Kona - Compare and Save

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Everything you should know

Cheapest round-trip
$544
Typical prices: $612-$900
Southwest
Fri 1/26Fri 2/2
MDW - KOA • 2 stops
Cheapest non-stop
$895
Typical prices: $1,183-$1,691
United Airlines
Tue 1/23Tue 1/30
ORD - KOA • Non-stop
Nonstop flights
1 day a week
You can fly direct with United Airlines. Average duration is 9h 16m
Direct flights
+1
Direct flights
+1
Top routes
ORD - KOA
Cheapest • 1% average savings
MDW - KOA
Most popular
Insights
Insights
When to book
9 weeks
in advance
Our data shows that travelers who book at least 9 weeks in advance save around 38% compared to booking last minute.
Insights
Insights
When to travel
February
Cheapest • 20% price drop
February
Most popular
Good to know
+1
Good to know
+1
Top layover airports
San Diego (SAN)
Cheapest • Avg $547 (round-trip)
Honolulu (HNL)
Shortest trip • 10h 58m (one-way)
Insights
Insights
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We hope you love your trip to Kailua-Kona!
Flight Deals
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Expert advice
Flight Deals

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

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

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

Tue, Jan 26 - Tue, Feb 2
Southwest Logo
10:15 am - 8:40 pmMDW  Chicago Midway-KOA Kona Intl
14h 25m2 stops Los Angeles Honolulu
Southwest Logo
9:25 pm - 12:30 pmKOA  Kona Intl-MDW Chicago Midway
11h 05m1 stop Las Vegas Harry Reid Intl
$544Southwest
Tue, Jan 26 - Tue, Feb 2
Multiple Airlines Logo
2:11 pm - 12:25 pmORD  Chicago O'Hare Intl-KOA Kona Intl
26h 14m1 stop Portland
Multiple Airlines Logo
10:34 am - 1:15 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
22h 41m1 stop San Diego
$547Multiple Airlines
Tue, Jan 26 - Tue, Feb 2
Delta Logo
7:15 am - 8:00 pmORD  Chicago O'Hare Intl-KOA Kona Intl
16h 45m2 stops Salt Lake City Seattle/Tacoma Intl
Delta Logo
9:40 pm - 4:57 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
15h 17m2 stops Seattle/Tacoma Intl Minneapolis St Paul
$559Delta
Sat, Feb 6 - Thu, Feb 11
Alaska Airlines Logo
2:13 pm - 4:50 pmORD  Chicago O'Hare Intl-KOA Kona Intl
30h 37m1 stop San Diego
Alaska Airlines Logo
12:50 pm - 1:54 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
21h 04m1 stop San Diego
$563Alaska Airlines
Tue, Jan 12 - Tue, Jan 26
Alaska Airlines Logo
8:00 am - 5:53 pmORD  Chicago O'Hare Intl-KOA Kona Intl
13h 53m1 stop Seattle/Tacoma Intl
Alaska Airlines Logo
8:40 am - 11:59 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
11h 19m1 stop Seattle/Tacoma Intl
$576Alaska Airlines
Mon, Jan 18 - Fri, Jan 22
Delta Logo
7:15 am - 2:57 pmORD  Chicago O'Hare Intl-KOA Kona Intl
11h 42m1 stop Salt Lake City
Delta Logo
10:45 pm - 1:53 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
11h 08m1 stop Los Angeles
$578Delta
Tue, Jan 26 - Tue, Feb 2
American Airlines Logo
7:20 am - 4:37 pmORD  Chicago O'Hare Intl-KOA Kona Intl
13h 17m1 stop Phoenix Sky Harbor Intl
American Airlines Logo
9:59 pm - 2:36 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
12h 37m1 stop Phoenix Sky Harbor Intl
$646American Airlines
Wed, Feb 10 - Tue, Feb 16
American Airlines Logo
7:20 am - 4:37 pmORD  Chicago O'Hare Intl-KOA Kona Intl
13h 17m1 stop Phoenix Sky Harbor Intl
American Airlines Logo
10:48 pm - 1:19 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
10h 31m1 stop Phoenix Sky Harbor Intl
$646American Airlines
Wed, Dec 16 - Sat, Dec 26
United Airlines Logo
10:25 am - 8:32 pmORD  Chicago O'Hare Intl-KOA Kona Intl
14h 07m1 stop San Francisco
United Airlines Logo
5:50 pm - 5:54 amKOA  Kona Intl-ORD Chicago O'Hare Intl
8h 04mnonstop
$874United Airlines
Sat, Jan 2 - Thu, Jan 7
United Airlines Logo
11:00 am - 4:19 pmORD  Chicago O'Hare Intl-KOA Kona Intl
9h 19mnonstop
United Airlines Logo
2:23 pm - 5:54 amKOA  Kona Intl-ORD Chicago O'Hare Intl
11h 31m1 stop Los Angeles
$874United Airlines
Booking Insights

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

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

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

Round-trip flights from Chicago to Kailua-Kona typically range from $612 to $900. The lowest price found in the past 5 days was $544, on Southwest.

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

There's little price difference between Chicago to Kailua-Kona routes. They average around $738 round-trip, based on KAYAK data over the past 12 months.

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

Based on deals KAYAK users found in the last 12 months, Monday is the cheapest day of the week to fly from Chicago to Kailua-Kona. It’s 8% cheaper than the average day, while Saturday is the most expensive, with prices 21% higher.

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

•February is the cheapest month to fly from Chicago to Kailua-Kona at $587 round-trip.
•November ($1,096) and June ($937) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 86% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are flights from Chicago to Kailua-Kona the cheapest?

Flights from Chicago to Kailua-Kona are cheapest 9 weeks before departure. Booking in this window typically costs about 38% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

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Expert advice

Expert advice for your flight from Chicago to Kailua-Kona

 
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 Chicago to Kailua-Kona flights

Low season

May

Cheapest flight

$289
Beat the crowds with an average 15% drop in travelers.
The most popular month to fly with an average 24% increase in travelers.
One-way flight from Chicago O'Hare Intl Airport to Kailua-Kona

When to book flights from Chicago to Kailua-Kona

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

Your Chicago to Kailua-Kona flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

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

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

    • Earliest: departs at 11:00 am and lands at 8:16 pm
    • Latest: departs at 11:15 am and lands at 8:31 pm.

    The flight takes about 9h 16m.

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

    Four cabin classes are available on flights from Chicago to Kailua-Kona:

    • Economy Class
    • Premium Economy Class
    • Business Class
    • First Class

    Prices vary by airline.

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

    A nonstop flight from Chicago to Kailua-Kona takes 9h 16m, covering 4,219 miles.

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

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

    Round-trip flights from Chicago to Kailua-Kona range from $612 to $900, with an average of $732 over the past 12 months. Anything below $612 counts as a good deal.

  • How expensive are last-minute Chicago to Kailua-Kona flights?

    Last-minute fares on this route (booked within two weeks of departure) run 34% above the $732 route average. Book 9 weeks before departure for the lowest fares.

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

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $547 round-trip via San Diego (SAN), compared to $1,392 for nonstop.

  • What is the standard checked-bag allowance on flights from Chicago to Kailua-Kona?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $40–$80 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • Have flight prices from Chicago to Kailua-Kona changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $554 to $3,979. That means the highest observed fare was about 7x higher than the lowest one.

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

    One-way fares from Chicago to Kailua-Kona are currently in line with typical prices for this route. Average one-way fares are about $394.

  • What car rental options are available at Kona Intl Airport (KOA)?

    Kona Intl Airport (KOA) hosts 5 major car rental companies, with daily rates averaging $66 for economy cars. Top options include:

    • Dollar
    • Thrifty
    • Hertz
    • Budget
    • Sixt

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

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

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

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

    • Los Angeles (LAX) - 38% of one-stop connections
    • Seattle/Tacoma Intl (SEA) - 25% of one-stop connections
    • Phoenix Sky Harbor Intl (PHX) - 9% of one-stop connections
    • Salt Lake City (SLC) - 7% of one-stop connections

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

    Yes. Flexible dates can save you up to 24% on flights from Chicago to Kailua-Kona. Monday is the cheapest departure day at $675 round-trip on average, while Saturday is the most expensive at $886, a difference of $211.

    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 airlines fly from Chicago to Kailua-Kona?

    Only United Airlines operates flights between Chicago and Kailua-Kona.

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

    Flying via Honolulu (HNL) gives the shortest average 1-stop total travel time at 10h 58m, compared with 11h 09m via San Francisco (SFO) and 11h 36m via Los Angeles (LAX).

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

    Kailua-Kona is 4 hours behind Chicago (Hawaii-Aleutian Time vs Central Time). Plan for the time shift when scheduling connections or first-day activities.

  • Which airlines offer extra legroom and free seat selection on Chicago to Kailua-Kona flights?

    Among airlines operating Chicago to Kailua-Kona flights:

    • United Airlines: offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • Which airlines include bags at no extra cost on Chicago to Kailua-Kona flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • United Airlines: a cabin bag in Economy Class class

    Bag allowance can vary by ticket type, cabin class, route and airline, so always check the fare details before booking.

  • Consider flying First Class when traveling with American Airlines from Chicago to Kailua-Kona. The airline's First Class ticket comes with priority privileges like speed through security, check-in and boarding at the airports, and priority bag handling after your flight. You also get to enjoy comfy seats, premium dining, and free in-flight entertainment.

    What are the common stopover options for flights from Chicago to Kailua Kona?

  • Flights from Chicago to Kailua Kona are generally connecting flights, as there are no direct flights at the moment. These flights have layovers in different cities depending on the airline. Most airlines flying from Chicago to Kailua-Kona have layovers in Seattle, Tacoma (SEA), Los Angeles (LAX), San Francisco (SFO), Atlanta (ATL), Honolulu (HNL), and Denver (DEN).

    Which airlines flying from Chicago to Kailua-Kona assist passengers with special needs?

  • Each airline flying from Chicago to Kailua-Kona offer assistance services for passengers with special needs. Every airline on this route runs a wheelchair assistance program to help travelers with reduced mobility easily get through the airport. If you need a wheelchair for your travel, we recommend informing your airline at least 48 hours before your flight to ensure it is available. These airlines also have attendants who assist passengers with special needs when boarding, moving to and from seats, or disembarking from planes.

    How can I get from the Kailua International Airport to Downtown Kailua-Kona?

  • There are several transportation options from Kona Airport to Kailua-Kona. Buses offer one of the most affordable and convenient ways of completing the trip from the airport to Kailua-Kona. Bus Line 202 runs from the airport to Luhia Street. The buses are operated by Hele-On Bus and depart the airport every 30 minutes. Alternatively, you can taxi or drive from the airport to Kailua-Kona.

    Which airlines flying from Chicago to Kailua-Kona offer better pet policies?

Your guide to booking Chicago to Kailua-Kona flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Monday departure and avoid flying on Saturday. On this route, Monday flights average $675, about $211 less than Saturday fares (24% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 9 weeks before you fly. On this route, that window historically saves about 38% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Chicago to Kailua-Kona trip for February. Fares historically average $587 round-trip in that month - typically $509 less than the most expensive month, which is November (based on the last 12 months).
  • If you have the time, taking a 1-stop flight through San Diego Airport (SAN) can be cheaper than flying direct. The cheapest layover option averages $547 round-trip on this route - about $846 less than direct flights (based on the last 12 months).
  • If you have a carry-on bag, consider flying with American Airlines on the NYC to BGR route. The airline allows you to board with one standard carry-on bag, which should have 40 lb at most of the weight. Its maximum dimensions must not exceed 22 x 14 x 9 inches. Also, you can have a personal item with sizes 18 x 14 x 8 inches, which must fit under the seat.
  • Flights from Chicago to Kailua-Kona depart from either Chicago O’Hare International Airport (ORD) or Chicago Midway Airport (MDW). Of the two Chicago airports, ORD handles more flights to Kailua-Kona than MDW. Therefore, consider flying from ORD to get more flight options.
  • Consider flying from Chicago MDW to Ellison Onizuka Kona International Airport (KOA) if you want to avoid long queues at the departure airport. MDW is usually less crowded than ORD. Therefore, you will spend less time getting through the airport for your flight.
  • Consider booking American Airlines or United when flying from Chicago ORD to Kailua-Kona. The airport is a hub for these two airlines; therefore, flying with them will give you more flight options. You will also get a way to access United Club and American Airlines Admirals Club at ORD by paying at the door.
  • You are welcome to use the pet relief areas at ORD when traveling with your pet from Chicago to Kailua-Kona. Outdoor pet relief areas are outside Door 1A, Door 2A, Door 5B, and near Lotto Booth in Terminal 1 Main Hall.

Prefer to fly direct from Chicago to Kailua-Kona?

 
Find which airlines fly direct from Chicago to Kona Intl Airport, which days they fly and book direct flights.

Direct departures

Chicago to Kona Intl

Saturday

United Airlines

United Airlines

See more direct flights

Direct returns

Kona Intl to Chicago

Saturday

United Airlines

United Airlines

See more direct flights

More options for your flight from Chicago to Kailua-Kona

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