
Flights from Naples to Chicago
Cheapest flights from Naples
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Thu, Sep 18 - Sun, Sep 21
RSW
Southwest Florida Intl.
ORD
O'Hare Intl.
$100 Roundtrip, found 4 days ago
$100
Roundtrip
found 4 days ago

Mon, Sep 15 - Thu, Sep 18
RSW
Southwest Florida Intl.
ORD
O'Hare Intl.
$110 Roundtrip, found 4 days ago
$110
Roundtrip
found 4 days ago

Thu, Sep 18 - Sun, Sep 21
RSW
Southwest Florida Intl.
ORD
O'Hare Intl.
$130 Roundtrip, found 4 days ago
$130
Roundtrip
found 4 days ago

Thu, Sep 18 - Sun, Sep 21
RSW
Southwest Florida Intl.
ORD
O'Hare Intl.
$159 Roundtrip, found 4 days ago
$159
Roundtrip
found 4 days ago

Thu, Sep 18 - Sun, Sep 21
RSW
Southwest Florida Intl.
ORD
O'Hare Intl.
$170 Roundtrip, found 4 days ago
$170
Roundtrip
found 4 days ago

Thu, Sep 18 - Sun, Sep 21
RSW
Southwest Florida Intl.
ORD
O'Hare Intl.
$180 Roundtrip, found 4 days ago
$180
Roundtrip
found 4 days ago
Thu, Sep 18 - Sun, Sep 21
RSW
Southwest Florida Intl.
ORD
O'Hare Intl.
$192 Roundtrip, found 4 days ago
$192
Roundtrip
found 4 days ago

Thu, Sep 18 - Sun, Sep 21
RSW
Southwest Florida Intl.
ORD
O'Hare Intl.
$210 Roundtrip, found 4 days ago
$210
Roundtrip
found 4 days ago

Thu, Sep 18 - Sun, Sep 21
RSW
Southwest Florida Intl.
ORD
O'Hare Intl.
$216 Roundtrip, found 4 days ago
$216
Roundtrip
found 4 days ago

Thu, Sep 18 - Sun, Sep 21
RSW
Southwest Florida Intl.
ORD
O'Hare Intl.
$218 Roundtrip, found 4 days ago
$218
Roundtrip
found 4 days ago

Thu, Sep 18 - Sun, Sep 21
RSW
Southwest Florida Intl.
ORD
O'Hare Intl.
$225 Roundtrip, found 4 days ago
$225
Roundtrip
found 4 days ago

Thu, Sep 18 - Sun, Sep 21
RSW
Southwest Florida Intl.
ORD
O'Hare Intl.
$230 Roundtrip, found 4 days ago
$230
Roundtrip
found 4 days ago

Thu, Sep 18 - Sun, Sep 21
RSW
Southwest Florida Intl.
ORD
O'Hare Intl.
$234 Roundtrip, found 4 days ago
$234
Roundtrip
found 4 days ago

Thu, Sep 18 - Sun, Sep 21
RSW
Southwest Florida Intl.
ORD
O'Hare Intl.
$236 Roundtrip, found 4 days ago
$236
Roundtrip
found 4 days ago

Thu, Sep 18 - Sun, Sep 21
RSW
Southwest Florida Intl.
MDW
Midway Intl.
$307 Roundtrip, found 4 days ago
$307
Roundtrip
found 4 days ago

Thu, Sep 18 - Sun, Sep 21
RSW
Southwest Florida Intl.
ORD
O'Hare Intl.
$323 Roundtrip, found 4 days ago
$323
Roundtrip
found 4 days ago

Thu, Sep 18 - Sun, Sep 21
RSW
Southwest Florida Intl.
MDW
Midway Intl.
$328 Roundtrip, found 4 days ago
$328
Roundtrip
found 4 days ago

Thu, Sep 18 - Sun, Sep 21
RSW
Southwest Florida Intl.
MDW
Midway Intl.
$379 Roundtrip, found 4 days ago
$379
Roundtrip
found 4 days ago

Thu, Sep 18 - Sun, Sep 21
RSW
Southwest Florida Intl.
MDW
Midway Intl.
$439 Roundtrip, found 4 days ago
$439
Roundtrip
found 4 days ago

Thu, Sep 18 - Sun, Sep 21
RSW
Southwest Florida Intl.
ORD
O'Hare Intl.
$516 Roundtrip, found 4 days ago
$516
Roundtrip
found 4 days ago