Chicago (ORD) to Naples (NAP) flight deal in economy from $676
$1,281 USD
-47%$676 USD
Verified 1 day agoDecember 2026
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Extremely Rare Availability
2% of dates checked are available within 10% of the lowest price
Tuesday, December 29th, 2026
10 round-trip options
Returning
Sun, Jan 3, 2027•5 Day Trip
$2,756 USD
Returning
Mon, Jan 4, 2027•6 Day Trip
$1,941 USD
Returning
Tue, Jan 5, 2027•7 Day Trip
$1,787 USD
Returning
Wed, Jan 6, 2027•8 Day Trip
$1,542 USD
Returning
Thu, Jan 7, 2027•9 Day Trip
$1,132 USD
Returning
Fri, Jan 8, 2027•10 Day Trip
$1,167 USD
Returning
Sat, Jan 9, 2027•11 Day Trip
$1,028 USD
Returning
Sun, Jan 10, 2027•12 Day Trip
$1,077 USD
Returning
Mon, Jan 11, 2027•13 Day Trip
$989 USD
Returning
Tue, Jan 12, 2027•14 Day Trip
$1,304 USD