MDW - KOA

$290 Find Cheap Flights from Chicago Midway Airport to Kailua-Kona - Compare and Save

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Everything you should know

Cheapest round-trip
$445
Typical prices: $663-$889
Delta
Sun 9/9Sat 9/22
MDW - KOA • 2 stops
Cheapest one-way
$290
Typical prices: $341-$467
Delta
Sat 11/10
MDW - KOA • 2 stops
Nonstop flights
Not available
There are currently no direct flights between Chicago Midway Airport and Kailua-Kona. You'll need to take a connecting flight to reach the destination.
Insights
Insights
When to travel
February
Cheapest • 54% price drop
February
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Los Angeles Los Angeles (LAX)
Cheapest • Avg $422 (round-trip)
Las Vegas Harry Reid Intl (LAS)
Shortest trip • 11h 44m (one-way)
Insights
Insights
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We hope you love your trip to Kailua-Kona!
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Booking Insights
Flight Deals

Cheap Flights from Midway to Kailua-Kona (MDW-KOA)

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

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

Wed, Sep 9 - Tue, Sep 22
Delta Logo
9:59 am - 7:15 pmMDW  Chicago Midway-KOA Kona Intl
14h 16m2 stops Minneapolis St Paul Los Angeles Los Angeles
Delta Logo
10:10 pm - 6:19 pmKOA  Kona Intl-MDW Chicago Midway
15h 09m2 stops Los Angeles Los Angeles Minneapolis St Paul
$445Delta
Thu, Sep 10 - Tue, Sep 22
Delta Logo
9:59 am - 7:15 pmMDW  Chicago Midway-KOA Kona Intl
14h 16m2 stops Minneapolis St Paul Los Angeles Los Angeles
Delta Logo
10:10 pm - 6:19 pmKOA  Kona Intl-MDW Chicago Midway
15h 09m2 stops Los Angeles Los Angeles Minneapolis St Paul
$475Delta
Sat, Sep 12 - Tue, Sep 22
Delta Logo
9:59 am - 7:15 pmMDW  Chicago Midway-KOA Kona Intl
14h 16m2 stops Minneapolis St Paul Los Angeles Los Angeles
Delta Logo
10:10 pm - 6:19 pmKOA  Kona Intl-MDW Chicago Midway
15h 09m2 stops Los Angeles Los Angeles Minneapolis St Paul
$475Delta
Wed, Sep 9 - Mon, Sep 21
Delta Logo
9:59 am - 7:15 pmMDW  Chicago Midway-KOA Kona Intl
14h 16m2 stops Minneapolis St Paul Los Angeles Los Angeles
Delta Logo
10:10 pm - 6:19 pmKOA  Kona Intl-MDW Chicago Midway
15h 09m2 stops Los Angeles Los Angeles Minneapolis St Paul
$475Delta
Thu, Sep 10 - Thu, Sep 24
Delta Logo
9:59 am - 7:15 pmMDW  Chicago Midway-KOA Kona Intl
14h 16m2 stops Minneapolis St Paul Los Angeles Los Angeles
Delta Logo
8:55 pm - 6:33 pmKOA  Kona Intl-MDW Chicago Midway
16h 38m2 stops Seattle/Tacoma Intl Detroit Metropolitan Wayne County
$475Delta
Wed, Oct 28 - Tue, Nov 3
Southwest Logo
6:05 am - 12:35 pmMDW  Chicago Midway-KOA Kona Intl
11h 30m1 stop Las Vegas Harry Reid Intl
Southwest Logo
9:30 pm - 5:20 pmKOA  Kona Intl-MDW Chicago Midway
15h 50m2 stops Las Vegas Harry Reid Intl Omaha Eppley Airfield
$500Southwest
Thu, Sep 10 - Mon, Sep 21
Delta Logo
9:59 am - 7:15 pmMDW  Chicago Midway-KOA Kona Intl
14h 16m2 stops Minneapolis St Paul Los Angeles Los Angeles
Delta Logo
10:10 pm - 6:19 pmKOA  Kona Intl-MDW Chicago Midway
15h 09m2 stops Los Angeles Los Angeles Minneapolis St Paul
$505Delta
Sat, Sep 12 - Mon, Sep 21
Delta Logo
9:59 am - 7:15 pmMDW  Chicago Midway-KOA Kona Intl
14h 16m2 stops Minneapolis St Paul Los Angeles Los Angeles
Delta Logo
10:10 pm - 6:19 pmKOA  Kona Intl-MDW Chicago Midway
15h 09m2 stops Los Angeles Los Angeles Minneapolis St Paul
$505Delta
Wed, Oct 28 - Tue, Nov 3
Southwest Logo
5:45 am - 2:20 pmMDW  Chicago Midway-KOA Kona Intl
13h 35m2 stops Phoenix Sky Harbor Intl Kahului
Southwest Logo
9:30 pm - 5:20 pmKOA  Kona Intl-MDW Chicago Midway
15h 50m2 stops Las Vegas Harry Reid Intl Omaha Eppley Airfield
$506Southwest
Tue, Jan 26 - Tue, Feb 2
Southwest Logo
7:25 am - 2:55 pmMDW  Chicago Midway-KOA Kona Intl
11h 30m1 stop Las Vegas Harry Reid Intl
Southwest Logo
9:30 pm - 12:35 pmKOA  Kona Intl-MDW Chicago Midway
11h 05m1 stop Las Vegas Harry Reid Intl
$524Southwest
Booking Insights

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

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

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

Round-trip flights from Chicago Midway Airport to Kailua-Kona start at $445. Prices are below average for this route right now, with typical round-trip fares ranging from $663 to $889. The lowest price found in the past 5 days was $445 on Delta.

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Key details for Chicago Midway Airport to Kailua-Kona flights

Low season

June

Cheapest flight

$290
Best time to beat the crowds but there is an average 35% increase in price.
Most popular time to fly and prices are also 54% lower on average.
Flight from Chicago Midway Airport to Kailua-Kona

When to book flights from Midway to Kailua-Kona

Are your dates flexible? Find out the best times to travel from Midway 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 Midway Airport to Kailua-Kona 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 Chicago Midway Airport to Kailua-Kona?

    Flights from Chicago Midway Airport to Kailua-Kona usually depart from Chicago Midway (MDW) and arrive at Kona Intl (KOA).

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

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

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

    Connecting flights from Chicago Midway Airport to Kailua-Kona most commonly pass through:

    • Las Vegas Harry Reid Intl (LAS) - 88% of one-stop connections
    • Los Angeles Los Angeles (LAX) - 13% of one-stop connections
    Together, these airports account for 101% of one-stop bookings on this route.

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

    Yes. Being flexible with your travel dates can save you up to 49% on the Chicago Midway Airport to Kailua-Kona route. Wednesday is the cheapest departure day at $494 round-trip on average, while Saturday is the most expensive at $954, a difference of $460. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

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

    A nonstop flight from Chicago Midway Airport to Kailua-Kona takes 0h 00m, covering 4,213 miles.

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

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

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

    One-way fares from Chicago Midway Airport to Kailua-Kona are currently lower than usual. Average one-way flight prices are about $309, which is 34% below the typical average for this route.

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

    Flying via Las Vegas Harry Reid Intl (LAS) gives the shortest average 1-stop total travel time at 11h 44m, compared with 11h 54m via Los Angeles Los Angeles (LAX).

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

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

  • 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 $28 for economy cars. Top options include:
    · Dollar
    · Thrifty
    · Budget
    · Hertz
    · Sixt

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

    Round-trip flights from Chicago Midway Airport to Kailua-Kona range from $663 to $889, with an average of $745 over the past 12 months. Anything below $663 counts as a good deal.

Your guide to booking Chicago Midway Airport to Kailua-Kona 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 $494 - about $460 less than Saturday (48% savings) based on the last 12 months.
  • If you can choose when to travel, plan your Chicago Midway Airport to Kailua-Kona trip for February. Fares historically average $342 round-trip in that month - typically $667 less than the most expensive month, which is June (based on the last 12 months).

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

Information on your arrival and departure airports

Chicago Midway Airport (MDW)
Kailua-Kona (KOA)