Chicago (ORD) to Naples (NAP) flight deal in economy from $676
$1,281 USD
-47%$676 USD
Verified 2 days agoOctober 2026
Mon
Tue
Wed
Thu
Fri
Sat
Sun
Extremely Rare Availability
2% of dates checked are available within 10% of the lowest price
Thursday, October 22nd, 2026
10 round-trip options
Returning
Tue, Oct 27, 2026•5 Day Trip
$1,132 USD
Returning
Wed, Oct 28, 2026•6 Day Trip
$1,757 USD
Returning
Thu, Oct 29, 2026•7 Day Trip
$1,080 USD
Returning
Fri, Oct 30, 2026•8 Day Trip
$1,946 USD
Returning
Sat, Oct 31, 2026•9 Day Trip
$1,861 USD
Returning
Sun, Nov 1, 2026•10 Day Trip
$989 USD
Returning
Mon, Nov 2, 2026•11 Day Trip
$964 USD
Returning
Tue, Nov 3, 2026•12 Day Trip
$863 USD
Returning
Wed, Nov 4, 2026•13 Day Trip
$826 USD
Returning
Thu, Nov 5, 2026•14 Day Trip
$826 USD