Kailua-Kona (KOA) to Chicago (MDW) flight deal in economy from $449
KOAKona International Airport
Kailua-Kona, United States
MDWMidway International Airport
Chicago, United States
$1,635 USD
-73%$449 USD
Verified about 3 hours agoSeptember 2026
Mon
Tue
Wed
Thu
Fri
Sat
Sun
Extremely Rare Availability
1% of dates checked are available within 10% of the lowest price
Tuesday, September 22nd, 2026
9 round-trip options
Returning
Sun, Sep 27, 2026•5 Day Trip
$1,121 USD
Returning
Mon, Sep 28, 2026•6 Day Trip
$552 USD
Returning
Tue, Sep 29, 2026•7 Day Trip
$552 USD
Returning
Wed, Sep 30, 2026•8 Day Trip
$552 USD
Returning
Fri, Oct 2, 2026•10 Day Trip
$2,481 USD
Returning
Sat, Oct 3, 2026•11 Day Trip
$1,663 USD
Returning
Sun, Oct 4, 2026•12 Day Trip
$2,481 USD
Returning
Mon, Oct 5, 2026•13 Day Trip
$1,768 USD
Returning
Tue, Oct 6, 2026•14 Day Trip
$1,207 USD