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CHI - KOA

$303 Find Cheap Flights from Chicago to Kailua-Kona - Compare and Save

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1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$559
Typical prices: $591-$901
Southwest
Mon 11/26Tue 12/4
MDW - KOA • 1 stop
Cheapest non-stop
$1,045
Typical prices: $1,183-$2,037
United Airlines
Wed 12/5Wed 12/12
ORD - KOA • Non-stop
Nonstop flights
Not available
There are currently no direct flights between Chicago and Kailua-Kona. You'll need to take a connecting flight to reach the destination.
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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 • 22% 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)
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Insights
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We hope you love your trip to Kailua-Kona!
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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

Thu, Nov 26 - Fri, Dec 4
Southwest Logo
6:05 am - 1:35 pmMDW  Chicago Midway-KOA Kona Intl
11h 30m1 stop Las Vegas Harry Reid Intl
Southwest Logo
9:30 pm - 12:15 pmKOA  Kona Intl-MDW Chicago Midway
10h 45m1 stop Las Vegas Harry Reid Intl
$559Southwest
Wed, Jan 27 - Wed, Feb 3
Multiple Airlines Logo
2:11 pm - 11:10 amORD  Chicago O'Hare Intl-KOA Kona Intl
24h 59m2 stops Portland Los Angeles
Multiple Airlines Logo
8:45 pm - 5:59 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
17h 14m2 stops Honolulu Seattle/Tacoma Intl
$562Multiple Airlines
Sat, Jan 30 - Thu, Feb 4
Alaska Airlines Logo
8:00 am - 10:29 pmORD  Chicago O'Hare Intl-KOA Kona Intl
18h 29m1 stop Seattle/Tacoma Intl
Alaska Airlines Logo
11:29 pm - 2:21 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
10h 52m1 stop Seattle/Tacoma Intl
$564Alaska Airlines
Sat, Jan 30 - Fri, Feb 5
Alaska Airlines Logo
8:00 am - 10:29 pmORD  Chicago O'Hare Intl-KOA Kona Intl
18h 29m1 stop Seattle/Tacoma Intl
Alaska Airlines Logo
8:51 am - 11:59 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
11h 08m1 stop Seattle/Tacoma Intl
$564Alaska Airlines
Sat, Dec 5 - Sat, Dec 12
Delta Logo
12:00 pm - 7:55 pmORD  Chicago O'Hare Intl-KOA Kona Intl
11h 55m1 stop Seattle/Tacoma Intl
Delta Logo
9:40 pm - 1:30 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
11h 50m1 stop Seattle/Tacoma Intl
$566Delta
Fri, Dec 11 - Sun, Jan 10
Delta Logo
6:40 am - 7:55 pmORD  Chicago O'Hare Intl-KOA Kona Intl
17h 15m1 stop Seattle/Tacoma Intl
Delta Logo
10:45 pm - 1:31 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
10h 46m1 stop Seattle/Tacoma Intl
$566Delta
Tue, Jan 26 - Thu, Feb 4
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
3:07 pm - 12:30 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
17h 23m1 stop Los Angeles
$620American Airlines
Tue, Jan 26 - Thu, Feb 4
American Airlines Logo
6:00 am - 4:37 pmORD  Chicago O'Hare Intl-KOA Kona Intl
14h 37m2 stops Dallas/Fort Worth Phoenix Sky Harbor Intl
American Airlines Logo
3:07 pm - 1:31 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
18h 24m1 stop Los Angeles
$625American Airlines
Wed, Jan 27 - Sat, Feb 13
United Airlines Logo
8:40 am - 4:50 pmORD  Chicago O'Hare Intl-KOA Kona Intl
12h 10m1 stop Denver Intl
United Airlines Logo
6:05 pm - 6:07 amKOA  Kona Intl-ORD Chicago O'Hare Intl
8h 02mnonstop
$854United Airlines
Sat, Jan 30 - Thu, Feb 4
United Airlines Logo
11:00 am - 4:19 pmORD  Chicago O'Hare Intl-KOA Kona Intl
9h 19mnonstop
United Airlines Logo
3:13 pm - 5:36 amKOA  Kona Intl-ORD Chicago O'Hare Intl
10h 23m1 stop San Francisco
$860United 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 $591 to $901. The lowest price found in the past 5 days was $559, 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 $736 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 16% 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 $569 round-trip.
•November ($1,096) and December ($916) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 92% 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

September

Cheapest flight

$298
Beat the crowds with an average 2% drop in travelers.
The most popular month to fly with an average 17% 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 8:12 pm
    • Latest: departs at 11:15 am and lands at 8:27 pm.

    The flight takes about 9h 12m.

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

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

    • Economy Class
    • Business Class
    • First Class

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

    A nonstop flight from Chicago to Kailua-Kona takes 9h 12m, 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 $591 to $901, with an average of $730 over the past 12 months. Anything below $591 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 36% above the $730 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 $559 to $4,868. That means the highest observed fare was about 9x 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 lower than usual. Average one-way flight prices are about $334, which is 14% below the typical average for this route.

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

    Kona Intl Airport (KOA) hosts 5 major car rental companies, with daily rates starting from around $29 for economy cars. Top options include:

    • Dollar
    • Thrifty
    • Budget
    • Hertz
    • 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) - 37% of one-stop connections
    • Seattle/Tacoma Intl (SEA) - 27% of one-stop connections
    • Phoenix Sky Harbor Intl (PHX) - 10% 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 21% 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 $848, a difference of $173.

    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 21m via Denver Intl (DEN).

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

    Kailua-Kona is 5 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 extra legroom; 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 and a checked bag in Economy 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 $173 less than Saturday fares (20% 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 $569 round-trip in that month - typically $527 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

Complete your trip to Kailua-Kona with a hotel stay or car rental

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