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Flights from Chicago to Kailua-Kona

What to know about flights from Chicago to Kailua-Kona?

The distance between Chicago and Kailua-Kona is approximately 6,793.37 km. It takes around 10 hours 46 minutes on average to fly from Chicago to Kailua-Kona. Based on Trip.com's data, travel demand peaks in July.

Cheapest one-way
$258
Delta Air Lines Delta Air Lines CHI-KOA 17h 16m · 1 stop Thu, Dec 3
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Cheapest round-trip
$425
Alaska Airlines Alaska Airlines CHI-KOA 12h 23m · 2 stops Thu, Oct 22 - Wed, Oct 28
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Recommended airlines
Delta Air Lines Delta Air Lines Cheapest · From $258 Delta Air Lines Delta Air Lines Most booked
When to travel
September
Cheapest
July
Peak season for travel
Route details
6,793.37 km
Flight distance
10h 46m
Average flight time

Explore the cheapest one-way and round-trip flights from Chicago to Kailua-Kona over the next 90 days, with one-way fares from $258 and round-trip from $425. Based on Trip.com's latest 7-day flight data.

      • ORD 7:20 AM
        12h 23m
        1 stop
        KOA 2:43 PM
        Chicago - Kailua-Kona | Thu, Oct 22 | Alaska Airlines
        KOA 9:03 PM
        14h 56m
        1 stop
        ORD 4:59 PM
        Kailua-Kona - Chicago | Wed, Oct 28 | Delta Air Lines
        $425 $905
        53% off
        53% off
        $905 $425
      • ORD 6:55 AM
        15h 43m
        1 stop
        KOA 5:38 PM
        Chicago - Kailua-Kona | Thu, Oct 22 | Delta Air Lines
        KOA 9:03 PM
        11h 26m
        1 stop
        ORD 1:29 PM
        Kailua-Kona - Chicago | Wed, Oct 28 | Delta Air Lines
        $427 $905
        53% off
        53% off
        $905 $427
      • ORD 5:57 AM
        14h 19m
        1 stop
        KOA 3:16 PM
        Chicago - Kailua-Kona | Thu, Oct 22 | American Airlines
        KOA 9:45 PM
        10h 14m
        1 stop
        ORD 12:59 PM
        Kailua-Kona - Chicago | Wed, Oct 28 | American Airlines
        $450 $905
        50% off
        50% off
        $905 $450
      • ORD 6:35 AM
        16h 3m
        1 stop
        KOA 5:38 PM
        Chicago - Kailua-Kona | Fri, Oct 16 | Delta Air Lines
        KOA 9:06 PM
        11h 24m
        1 stop
        ORD 1:30 PM
        Kailua-Kona - Chicago | Fri, Oct 23 | Delta Air Lines
        $543
        40% off
        $905 $543
      • ORD 7:20 AM
        12h 23m
        1 stop
        KOA 2:43 PM
        Chicago - Kailua-Kona | Fri, Oct 16 | Alaska Airlines
        KOA 9:06 PM
        14h 47m
        1 stop
        ORD 4:53 PM
        Kailua-Kona - Chicago | Fri, Oct 23 | Delta Air Lines
        $573
        37% off
        $905 $573
      • ORD 6:00 AM
        14h 17m
        1 stop
        KOA 3:17 PM
        Chicago - Kailua-Kona | Fri, Oct 16 | American Airlines
        KOA 9:06 PM
        14h 47m
        1 stop
        ORD 4:53 PM
        Kailua-Kona - Chicago | Fri, Oct 23 | Delta Air Lines
        $647
        28% off
        $905 $647
      • ORD 5:00 AM
        14h 2m
        1 stop
        KOA 3:02 PM
        Chicago - Kailua-Kona | Fri, Nov 20 | American Airlines
        KOA 10:09 PM
        12h 51m
        1 stop
        ORD 3:00 PM
        Kailua-Kona - Chicago | Tue, Nov 24 | American Airlines
        $769
        15% off
        $905 $769
      • ORD 6:35 AM
        16h 3m
        1 stop
        KOA 5:38 PM
        Chicago - Kailua-Kona | Sat, Oct 24 | Delta Air Lines
        KOA 9:06 PM
        11h 54m
        1 stop
        ORD 2:00 PM
        Kailua-Kona - Chicago | Sat, Oct 31 | Delta Air Lines
        $790
        13% off
        $905 $790
      • ORD 7:20 AM
        12h 32m
        1 stop
        KOA 3:52 PM
        Chicago - Kailua-Kona | Fri, Nov 20 | Alaska Airlines
        KOA 8:45 PM
        11h 18m
        1 stop
        ORD 12:03 PM
        Kailua-Kona - Chicago | Tue, Nov 24 | Delta Air Lines
        $816
        10% off
        $905 $816
      • ORD 6:40 AM
        16h 45m
        1 stop
        KOA 7:25 PM
        Chicago - Kailua-Kona | Fri, Nov 20 | Delta Air Lines
        KOA 10:45 PM
        10h 52m
        1 stop
        ORD 1:37 PM
        Kailua-Kona - Chicago | Tue, Nov 24 | Delta Air Lines
        $823
        9% off
        $905 $823
      • CHI 1:00 PM
        17h 25m
        1 stop
        KOA 2:00 PM
        Chicago - Kailua-Kona | Wed, Oct 14 | Normal Airline
        KOA 3:00 PM
        6h
        Nonstop
        CHI 4:00 PM
        Kailua-Kona - Chicago | Fri, Oct 16 | Normal Airline
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      • Cheapest nonstop
        ORD 11:15 AM
        9h 1m
        Nonstop
        KOA 4:16 PM
        Chicago - Kailua-Kona | Sat, Dec 5 | United Airlines
        $760 $836
        9% off
        9% off
        $836 $760
      • ORD 6:40 AM
        17h 16m
        1 stop
        KOA 7:56 PM
        Chicago - Kailua-Kona | Thu, Dec 3 | Delta Air Lines
        $258 $836
        69% off
        69% off
        $836 $258
      • ORD 6:40 AM
        14h 2m
        1 stop
        KOA 4:42 PM
        Chicago - Kailua-Kona | Tue, Dec 1 | American Airlines
        $263 $836
        69% off
        69% off
        $836 $263
      • ORD 6:35 AM
        16h 3m
        1 stop
        KOA 5:38 PM
        Chicago - Kailua-Kona | Wed, Oct 21 | Delta Air Lines
        $281
        66% off
        $836 $281
      • ORD 7:20 AM
        12h 32m
        1 stop
        KOA 3:52 PM
        Chicago - Kailua-Kona | Mon, Nov 16 | Alaska Airlines
        $291
        65% off
        $836 $291
      • ORD 7:30 AM
        11h 11m
        1 stop
        KOA 2:41 PM
        Chicago - Kailua-Kona | Tue, Nov 10 | Delta Air Lines
        $292
        65% off
        $836 $292
      • ORD 7:30 AM
        11h 11m
        1 stop
        KOA 2:41 PM
        Chicago - Kailua-Kona | Wed, Nov 11 | Delta Air Lines
        $296
        65% off
        $836 $296
      • ORD 6:40 AM
        16h 45m
        1 stop
        KOA 7:25 PM
        Chicago - Kailua-Kona | Thu, Nov 12 | Delta Air Lines
        $296
        65% off
        $836 $296
      • ORD 6:40 AM
        16h 45m
        1 stop
        KOA 7:25 PM
        Chicago - Kailua-Kona | Mon, Nov 16 | Delta Air Lines
        $308
        63% off
        $836 $308
      • ORD 6:50 AM
        12h 12m
        1 stop
        KOA 3:02 PM
        Chicago - Kailua-Kona | Wed, Nov 4 | American Airlines
        $319
        62% off
        $836 $319
      • ORD 6:50 AM
        12h 12m
        1 stop
        KOA 3:02 PM
        Chicago - Kailua-Kona | Fri, Nov 27 | American Airlines
        $319
        62% off
        $836 $319
      • CHI 1:00 PM
        17h 25m
        1 stop
        KOA 2:00 PM
        Chicago - Kailua-Kona | Wed, Oct 14 | Normal Airline
        Find more flights
        Find more flights

Flight.News
Flights from Chicago to Kailua-Kona operate an average of 1 times per day over the past 7 days, with a 57.1% on-time departure rate and a 100.0% on-time arrival rate.

Which airlines are the most popular for Chicago to Kailua-Kona flights?

You can choose from 2 airlines that fly from Chicago to Kailua-Kona, including Delta Air Lines, Alaska Airlines, Delta Air Lines has lowest fares on this route.
Delta Air Lines logo Delta Air Lines
Alaska Airlines logo Alaska Airlines
Airlines are determined based on actual purchased flight tickets from Chicago to Kailua-Kona according to previous 12 months data from Trip.com.

Frequently Asked Questions

  • What are the cheapest flights from Chicago to Kailua-Kona (CHI-KOA)?

    Based on Trip.com data, Delta Air Lines offers one-way fares as low as $258 on Cheapest nonstop routes (e.g. ORD to KOA on Thu, Dec 3), while Alaska Airlines offers Cheapest nonstop round-trips from $425 departing on Thu, Oct 22 and returning on Wed, Oct 28.
  • At the moment, several airlines serve connecting flights from Chicago to Kailua-Kona, including: Delta Air Lines Alaska Airlines Selected airlines are based on historical data collected from flight bookings made by users on Trip.com within the last 90 days.
  • It takes around 10 hours 46 minutes to fly from Chicago (CHI) to Kailua-Kona (KOA).
  • By analyzing data from all airlines on the Trip.com flight calendar, it looks like the best time to book a flight from Chicago to Kailua-Kona is around 40 days (6 weeks) in advance, and the best time to fly is usually on Tuesday, Wednesday, and Saturday. Tuesday typically offers the cheapest flights for departure, while Saturday offers the best return deals.
  • To find best deals on flights from Chicago to Kailua-Kona, you can use various tools on Trip.com:
    · Be flexible with your travel dates to get the cheapest flight deal. Now the cheapest flight deal is on Thu, Dec 3, with one-way flights priced at just $258.
    · Compare airlines strategically. Budget carriers often provide the lowest base fares, while we found the most affordable airline currently operating on this route is United Airlines.
    · Set up price alerts to easily monitor ticket prices without having to check every day.
    · Check Trip.com flight deals and promo codes frequently.
    · Avoid peak season unless you book very early. It seems the peak season for Kailua-Kona travel is around July.
    · Get exclusive promo codes for Trip.com app users.
  • The cheapest months to fly from Chicago to Kailua-Kona is September, when demand for travel is lower.
  • After crunching the numbers on our October flight calendar, it's currently cheapest to fly from Chicago to Kailua-Kona on October 22, 2026 with Alaska Airlines, with prices starting at $450.
  • You can arrive at any of the following airports in Kailua-Kona: Ellison Onizuka Kona International Airport (KOA). Flights from O'Hare International Airport to Ellison Onizuka Kona International Airport (ORD-KOA) are by far the most popular option for this route.
  • The time difference between Kailua-Kona and Chicago is 4h.
  • Tickets can only be changed or canceled if permitted by airline policy. To submit a change or cancellation request, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and segment, and submit a request. Please note that additional charges may apply according to the airline ticket policy. However, if the flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For more details about change and cancellation policies, please check the customer support pages.
  • Based on Trip.com data for flights departing in the next 30 days, the average one-way fare from Chicago to Kailua-Kona is $467. Fares vary by travel date, airline and availability.
  • Based on Trip.com data for travel in the next 30 days, the average round-trip fare from Chicago to Kailua-Kona is $1,030. The final price depends on the outbound and return dates, airline and fare conditions.
  • Enter Chicago and Kailua-Kona, choose your travel dates and passengers, then compare flights by price, duration and baggage. Select a fare, review the change and cancellation rules, enter traveler details and complete payment to receive your confirmation.

Explore More Popular Flights

Note: Prices shown on this page are estimated lowest price and include all taxes and fees found in the last 24 hours.

Book with no extra fees

Prices displayed in this page are all-inclusive prices (incl. taxes, fuel surcharge, civil aviation development fund, etc) with all fees confirmed before payment. Fees for luggage, meals, WLAN, or other additional services are also included as shown in the flight cards.

Real-time pricing updates

Prices, availability, and travel information on this page were updated within last 24 hours—even in real-time. The more popular the route, the more precise the data.

Change & Cancellation Policy

Trip.com displays flight cancellation and change policies for each flight ticket during the booking process, including fees and applicable conditions. Please check the following scenarios:
Voluntary cancellation/change:
To submit a change or cancellation request, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and segment, and submit a request. Please note that additional charges may apply according to the airline ticket policy.
Cancellation/change due to a flight schedule change:
If the flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For more details about change and cancellation policies, please check the customer support pages.