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

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Cheap Flights from MDW to KOA starting at $244 One Way, $562 Round Trip

Prices starting at $562 for return flights and $244 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.

Sun, May 3 - Fri, May 8
MDW
Chicago
KOA
Kona Coast
$562 Roundtrip, found 6 days ago
$562
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Sun, May 3 from Chicago to Kona Coast, returning Fri, May 8, priced at $562 found 6 days ago
Thu, Apr 16 - Fri, Apr 17
MDW
Chicago
KOA
Kona Coast
$566 Roundtrip, found 5 days ago
$566
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Thu, Apr 16 from Chicago to Kona Coast, returning Fri, Apr 17, priced at $566 found 5 days ago
Sun, May 3 - Fri, May 8
MDW
Chicago
KOA
Kona Coast
$586 Roundtrip, found 6 days ago
$586
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Sun, May 3 from Chicago to Kona Coast, returning Fri, May 8, priced at $586 found 6 days ago
Sun, May 3 - Fri, May 8
MDW
Chicago
KOA
Kona Coast
$587 Roundtrip, found 6 days ago
$587
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Sun, May 3 from Chicago to Kona Coast, returning Fri, May 8, priced at $587 found 6 days ago
Sun, May 3 - Fri, May 8
MDW
Chicago
KOA
Kona Coast
$592 Roundtrip, found 6 days ago
$592
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Sun, May 3 from Chicago to Kona Coast, returning Fri, May 8, priced at $592 found 6 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 Mar 16 to Mar 17
$261 total
Mar 16 - Mar 17
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 ...
8.2/10 Very Good! (2,879 reviews)
Room was dated feeling, did not feel like the most clean room, bathroom looked worn

Reviewed on Mar 14, 2026

Royal Kona Resort
PACIFIC 19 Kona

PACIFIC 19 Kona

3.5 out of 5
75-5646 Palani Rd Kailua-Kona HI
$189 nightly
The price is $225 total per night from Mar 26 to Mar 27
$225 total
Mar 26 - Mar 27
Total with taxes and fees
Stay at this hotel in Kailua-Kona. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Our guests praise the pool and the helpful staff in our reviews. ...
8.4/10 Very Good! (2,397 reviews)
The room was comfortable

Reviewed on Mar 15, 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
$312 nightly
The price is $370 total per night from Mar 29 to Mar 30
$370 total
Mar 29 - Mar 30
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! (1,007 reviews)
Great location, nice imenities.

Reviewed on Mar 15, 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 Mar 16 to Mar 17
$261 total
Mar 16 - Mar 17
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 ...
8.2/10 Very Good! (2,879 reviews)
Room was dated feeling, did not feel like the most clean room, bathroom looked worn

Reviewed on Mar 14, 2026

Royal Kona Resort
PACIFIC 19 Kona

PACIFIC 19 Kona

3.5 out of 5
75-5646 Palani Rd Kailua-Kona HI
$189 nightly
The price is $225 total per night from Mar 26 to Mar 27
$225 total
Mar 26 - Mar 27
Total with taxes and fees
Stay at this hotel in Kailua-Kona. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Our guests praise the pool and the helpful staff in our reviews. ...
8.4/10 Very Good! (2,397 reviews)
The room was comfortable

Reviewed on Mar 15, 2026

PACIFIC 19 Kona
OUTRIGGER Kona Resort & Spa

OUTRIGGER Kona Resort & Spa

4 out of 5
78-128 Ehukai Street Kailua-Kona HI
$324 nightly
The price is $385 total per night from Mar 28 to Mar 29
$385 total
Mar 28 - Mar 29
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! (1,008 reviews)
Ocean view from balcony. Clean room. Pool very inviting with 2 hot tubs. Water slide I didn’t try. Lovely property to walk around too. Meal choices were limited menus but sufficient.

Reviewed on Mar 15, 2026

OUTRIGGER Kona Resort & Spa
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.

Kailua-Kona Hotels With Airport Transportation

Banyan Tree Sanctuary

Banyan Tree Sanctuary

3 out of 5
73-4464 Kohanaiki Road Kailua-Kona HI
Book a stay at this spa guesthouse in Kailua-Kona. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Lyman Kona Coffee Farms and ...
9/10 Wonderful! (83 reviews)
Room was small but comfortable. couldn't leave slider open at night because frogs were so loud and it got too hot in the room with no AC

Reviewed on Oct 14, 2024

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Banyan Tree Sanctuary
Kona Hawaii Guesthouse

Kona Hawaii Guesthouse

2.5 out of 5
77-362 Paulina place Kailua-Kona HI
Stay at this guesthouse in Kailua-Kona. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Magic Sands Beach and Kona Le'a Plantation ...
4.6/10 (48 reviews)
This place is trashed!!!!! DO NOT BOOK this place!!! Pictures are NOT what they represent at all!!!

Reviewed on May 31, 2024

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Kona Hawaii Guesthouse
Club Wyndham Mauna Loa Village

Club Wyndham Mauna Loa Village

3.5 out of 5
78-7190 Kaleiopapa St. Kailua-Kona HI
Book a stay at this golf hotel in Kailua-Kona. Enjoy free WiFi, 6 outdoor pools, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. ...
9/10 Wonderful! (436 reviews)
Check in was the worst! Arrived in the evening and although the front desk clerk tried to give directions to the building/room it was impossible to find. Very POOR lighting so bad I fell on the walkway! The room was clean and spacious Cute sign instructing to remove shoes but the carpet had nails ...

Reviewed on Jan 22, 2026

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Club Wyndham Mauna Loa Village
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.

Low Priced Kailua-Kona Hotels

Hampton Inn by Hilton Kailua-Kona Bay

Hampton Inn by Hilton Kailua-Kona Bay

2.5 out of 5
75-5739 Alii Dr Kailua-Kona HI
Stay at this hotel in Kailua-Kona. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Popular attractions Magic Sands Beach and Kona Inn Shopping ...
6.8/10 (993 reviews)
We did not stay at Uncle Billys hotel. It was closed but we were booked at a hotel 7 miles away

Reviewed on Jan 1, 2022

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Hampton Inn by Hilton Kailua-Kona Bay
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! (1,426 reviews)
Nice pool, used it once. Clean, large condo with well equipped kitchen. Large balconies.

Reviewed on Mar 14, 2026

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Kona Coast Resort
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 Mar 16 to Mar 17
$261 total
Mar 16 - Mar 17
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 ...
8.2/10 Very Good! (2,879 reviews)
Room was dated feeling, did not feel like the most clean room, bathroom looked worn

Reviewed on Mar 14, 2026

Royal Kona Resort
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! (1,426 reviews)
Nice pool, used it once. Clean, large condo with well equipped kitchen. Large balconies.

Reviewed on Mar 14, 2026

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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 Magic Sands Beach and Haleo ...
7.8/10 Good! (1,002 reviews)

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

Travelers say...
Beautiful, clean room close to the pool. Amazingly high ceilings. Wonderful interactions with the staff. I can’t wait to go back!

Reviewed on Feb 3, 2026

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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! (985 reviews)
Our condo was perfect, comfortable bed, great barbeque grill. Internet was not good.

Reviewed on Mar 5, 2026

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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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