Cheap flights from MDW to KOA (Midway Intl. to Kona Intl.)

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Cheap Flights from MDW to KOA starting at $283 One Way, $554 Round Trip

Prices starting at $554 for return flights and $283 for one-way flights to Kona Intl. were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Tue, Jan 26 - Tue, Feb 2
MDW
Chicago
KOA
Kona Coast
$554 Roundtrip, found 5 days ago
$554
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Tue, Jan 26 from Chicago to Kona Coast, returning Tue, Feb 2, priced at $554 found 5 days ago
Tue, Jan 26 - Tue, Feb 2
MDW
Chicago
KOA
Kona Coast
$560 Roundtrip, found 5 days ago
$560
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Tue, Jan 26 from Chicago to Kona Coast, returning Tue, Feb 2, priced at $560 found 5 days ago
Tue, Jan 26 - Tue, Feb 2
MDW
Chicago
KOA
Kona Coast
$565 Roundtrip, found 5 days ago
$565
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Tue, Jan 26 from Chicago to Kona Coast, returning Tue, Feb 2, priced at $565 found 5 days ago
Tue, Jan 26 - Tue, Feb 2
MDW
Chicago
KOA
Kona Coast
$570 Roundtrip, found 5 days ago
$570
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Tue, Jan 26 from Chicago to Kona Coast, returning Tue, Feb 2, priced at $570 found 5 days ago
Tue, Jan 26 - Tue, Feb 2
MDW
Chicago
KOA
Kona Coast
$570 Roundtrip, found 5 days ago
$570
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Tue, Jan 26 from Chicago to Kona Coast, returning Tue, Feb 2, priced at $570 found 5 days ago

Hotel Ideas near Kona Intl.

Airport Hotels near Kona Intl.

Royal Kona Resort

Royal Kona Resort

4 out of 5
75-5852 Alii Dr Kailua-Kona HI
$219 nightly
The price is $261 total per night from Aug 4 to Aug 5
$261 total
Aug 4 - Aug 5
Total with taxes and fees
Book a stay at this beach hotel in Kailua-Kona. Enjoy a full-service spa, breakfast (surcharge), and a fitness center. Our guests praise the pool and the restaurant ...
Royal Kona Resort
PACIFIC 19 Kona

PACIFIC 19 Kona

3.5 out of 5
75-5646 Palani Rd Kailua-Kona HI
$194 nightly
The price is $231 total per night from Aug 18 to Aug 19
$231 total
Aug 18 - Aug 19
Total with taxes and fees
Stay at this hotel in Kailua-Kona. Enjoy parking (surcharge), a 24-hour front desk, and laundry facilities. Our guests praise the pool and the helpful staff ...
8.4/10 Very Good! (2,703 reviews)
"This place is located super conveniently within walking distance of a lot of cool spots!"

Reviewed on Aug 3, 2026

PACIFIC 19 Kona
Courtyard by Marriott King Kamehameha's Kona Beach Hotel

Courtyard by Marriott King Kamehameha's Kona Beach Hotel

3.5 out of 5
75-5660 Palani Road Kailua-Kona HI
$282 nightly
The price is $335 total per night from Aug 12 to Aug 13
$335 total
Aug 12 - Aug 13
Total with taxes and fees
Book a stay at this beach hotel in Kailua-Kona. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
8.4/10 Very Good! (1,002 reviews)
"Very comfortable, clean and quiet hotel with lots of amenities! Great location, very nice beach that they clean every morning, beautiful pool, beach towels you can exchange for clean ones as needed, and much more. If you don’t want the expensive buffet breakfast, King’s coffee shop has excellent ..."

Reviewed on Aug 2, 2026

Courtyard by Marriott King Kamehameha's Kona Beach Hotel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotels In Kailua-Kona

Royal Kona Resort

Royal Kona Resort

4 out of 5
75-5852 Alii Dr Kailua-Kona HI
$219 nightly
The price is $261 total per night from Aug 4 to Aug 5
$261 total
Aug 4 - Aug 5
Total with taxes and fees
Book a stay at this beach hotel in Kailua-Kona. Enjoy a full-service spa, breakfast (surcharge), and a fitness center. Our guests praise the pool and the restaurant ...
Royal Kona Resort
OUTRIGGER Kona Resort & Spa

OUTRIGGER Kona Resort & Spa

4 out of 5
78-128 Ehukai Street Kailua-Kona HI
$295 nightly
The price is $350 total per night from Sep 1 to Sep 2
$350 total
Sep 1 - Sep 2
Total with taxes and fees
Book a stay at this golf resort in Kailua-Kona. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in our ...
8.8/10 Excellent! (1,170 reviews)
"My family and I had a very nice stay at the Outrigger in Kona. The hotel was close to everything yet far enough away from downtown Kona that it felt peaceful and secluded. We enjoyed the hotel room, the gym, and the beautiful area surrounding the hotel. We had one problem with our air conditioner ..."

Reviewed on Aug 2, 2026

OUTRIGGER Kona Resort & Spa
PACIFIC 19 Kona

PACIFIC 19 Kona

3.5 out of 5
75-5646 Palani Rd Kailua-Kona HI
$194 nightly
The price is $231 total per night from Aug 18 to Aug 19
$231 total
Aug 18 - Aug 19
Total with taxes and fees
Stay at this hotel in Kailua-Kona. Enjoy parking (surcharge), a 24-hour front desk, and laundry facilities. Our guests praise the pool and the helpful staff ...
8.4/10 Very Good! (2,703 reviews)
"This place is located super conveniently within walking distance of a lot of cool spots!"

Reviewed on Aug 3, 2026

PACIFIC 19 Kona
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Family Friendly Hotels in Kailua-Kona

Kona Coast Resort

Kona Coast Resort

3.5 out of 5
78-6842 Alii Dr Kailua-Kona HI
Book a stay at this golf hotel in Kailua-Kona. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
9.2/10 Wonderful! (1,457 reviews)
"Loved the property. Spacious and lovely."

Reviewed on Aug 3, 2026

Get rates
Kona Coast Resort
Outrigger Kona Resort and Spa

Outrigger Kona Resort and Spa

4.5 out of 5
Ehukai Street, 78-128 Kailua-Kona HI
Book a stay at this luxury hotel in Kailua-Kona. Enjoy 2 outdoor pools, a full-service spa, and 4 restaurants. Popular attractions Kahalu'u Beach Park and Magic ...
8/10 Very Good! (997 reviews)

Families like: Outdoor pools, game room, close to beach, bicycle rentals

Travelers say...
"Overall the resort was amazing....we loved it all. Only room for improvement is at the piko dinner...food was mid and music at pool area"

Reviewed on Jul 6, 2026

Get rates
Outrigger Kona Resort and Spa
Club Wyndham Kona

Club Wyndham Kona

3.5 out of 5
75-5961 Alii Dr. Kailua-Kona HI
Stay at this hotel in Kailua-Kona. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff in our reviews. Popular attractions ...
9/10 Wonderful! (1,000 reviews)
"The grounds were well maintained with historical and natural features. The apartment had all the necessities for kitchen, bath and outdoor fun like beach towels. Each room is very quiet and perfect for privacy. I am not sure if every apartment has them, but our apartment had a small cooler for our ..."

Reviewed on Jul 24, 2026

Get rates
Club Wyndham Kona
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

MDW to KOA Route Info

Origin Airport
Destination Airport
Number Of Airlines Serving
Distance
Shortest Flight Departure Time
Shortest Flight Departure Date
MDW Address & GPS
Address:
5700 South Cicero
Chicago IL, 60638
United States
IATA Code:
MDW
Longitude:
-87.740871
Latitude:
41.788136
Time Zone:
America/Chicago
KOA Address & GPS
Address:
Kailua-Kona HI, 96734
United States
IATA Code:
KOA
Longitude:
-156.041077
Latitude:
19.736174
Time Zone:
Pacific/Honolulu

Frequently asked questions

What is the shortest flight from Chicago Airport to Kona Intl. Airport (KOA)?
Racked up some extra air miles? Take the opportunity to upgrade to a seat with more room on your Chicago to Kailua-Kona trip. With a minimum flight duration of 10 hours and 37 minutes, you'll want to be as comfortable as possible.
How many hours flight from MDW to Ellison Onizuka Kona Intl. Airport at Keāhole?
From the time you jet off from Midway Airport to the moment the plane grinds to a halt in Kona Intl. Airport (KOA), you will have been in the air for approximately 10 hours and 41 minutes. Get through this lengthy flight by bringing all the essentials such as a travel pillow, earplugs, an eye mask and a warm sweater.
What airlines have the most flights from Chicago Airport to KOA?
You'll need to make at least one stopover if you're flying from MDW to KOA. For now, there are no airlines that advertise direct flights on this route.

Map To Nearby Hotels

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.

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