Flights from Chicago to Positano

Cheapest flights from Chicago

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.

Mon, Sep 22 - Sat, Oct 11

ORD

O'Hare Intl.

NAP

Naples Intl.

$622 Roundtrip, found 6 days ago

$622

Roundtrip

found 6 days ago

Select Turkish Airlines flight, departing Mon, Sep 22 from O'Hare Intl. to Naples Intl., returning Sat, Oct 11, priced at $622 found 6 days ago

Mon, Sep 22 - Tue, Oct 7

ORD

O'Hare Intl.

NAP

Naples Intl.

$647 Roundtrip, found 6 days ago

$647

Roundtrip

found 6 days ago

Select Turkish Airlines flight, departing Mon, Sep 22 from O'Hare Intl. to Naples Intl., returning Tue, Oct 7, priced at $647 found 6 days ago

Sun, Sep 21 - Sat, Oct 11

ORD

O'Hare Intl.

NAP

Naples Intl.

$667 Roundtrip, found 6 days ago

$667

Roundtrip

found 6 days ago

Select Turkish Airlines flight, departing Sun, Sep 21 from O'Hare Intl. to Naples Intl., returning Sat, Oct 11, priced at $667 found 6 days ago

Tue, Sep 23 - Tue, Oct 7

ORD

O'Hare Intl.

NAP

Naples Intl.

$672 Roundtrip, found 6 days ago

$672

Roundtrip

found 6 days ago

Select Turkish Airlines flight, departing Tue, Sep 23 from O'Hare Intl. to Naples Intl., returning Tue, Oct 7, priced at $672 found 6 days ago

Mon, Sep 22 - Mon, Oct 6

ORD

O'Hare Intl.

NAP

Naples Intl.

$687 Roundtrip, found 6 days ago

$687

Roundtrip

found 6 days ago

Select Turkish Airlines flight, departing Mon, Sep 22 from O'Hare Intl. to Naples Intl., returning Mon, Oct 6, priced at $687 found 6 days ago

Sun, Sep 21 - Tue, Oct 7

ORD

O'Hare Intl.

NAP

Naples Intl.

$692 Roundtrip, found 6 days ago

$692

Roundtrip

found 6 days ago

Select Turkish Airlines flight, departing Sun, Sep 21 from O'Hare Intl. to Naples Intl., returning Tue, Oct 7, priced at $692 found 6 days ago

Sun, May 11 - Wed, May 21

ORD

O'Hare Intl.

NAP

Naples Intl.

$827 Roundtrip, found 2 days ago

$827

Roundtrip

found 2 days ago

Select ITA Airways flight, departing Sun, May 11 from O'Hare Intl. to Naples Intl., returning Wed, May 21, priced at $827 found 2 days ago

Sun, Jun 8 - Tue, Jun 17

ORD

O'Hare Intl.

NAP

Naples Intl.

$839 Roundtrip, found 19 hours ago

$839

Roundtrip

found 19 hours ago

Select Delta flight, departing Sun, Jun 8 from O'Hare Intl. to Naples Intl., returning Tue, Jun 17, priced at $839 found 19 hours ago

Fri, Jun 6 - Sat, Jun 14

ORD

O'Hare Intl.

NAP

Naples Intl.

$1,017 Roundtrip, found 19 hours ago

$1,017

Roundtrip

found 19 hours ago

Select Air Canada flight, departing Fri, Jun 6 from O'Hare Intl. to Naples Intl., returning Sat, Jun 14, priced at $1,017 found 19 hours ago

Fri, Jun 6 - Sat, Jun 14

ORD

O'Hare Intl.

NAP

Naples Intl.

$1,022 Roundtrip, found 19 hours ago

$1,022

Roundtrip

found 19 hours ago

Select United flight, departing Fri, Jun 6 from O'Hare Intl. to Naples Intl., returning Sat, Jun 14, priced at $1,022 found 19 hours ago

Fri, Jun 6 - Sat, Jun 14

ORD

O'Hare Intl.

NAP

Naples Intl.

$1,056 Roundtrip, found 19 hours ago

$1,056

Roundtrip

found 19 hours ago

Select Lufthansa flight, departing Fri, Jun 6 from O'Hare Intl. to Naples Intl., returning Sat, Jun 14, priced at $1,056 found 19 hours ago

Thu, May 8 - Fri, May 16

ORD

O'Hare Intl.

NAP

Naples Intl.

$1,107 Roundtrip, found 2 days ago

$1,107

Roundtrip

found 2 days ago

Select American Airlines flight, departing Thu, May 8 from O'Hare Intl. to Naples Intl., returning Fri, May 16, priced at $1,107 found 2 days ago

Fri, Jun 6 - Sat, Jun 14

ORD

O'Hare Intl.

NAP

Naples Intl.

$1,111 Roundtrip, found 19 hours ago

$1,111

Roundtrip

found 19 hours ago

Select Swiss International Air Lines flight, departing Fri, Jun 6 from O'Hare Intl. to Naples Intl., returning Sat, Jun 14, priced at $1,111 found 19 hours ago

Fri, Jun 6 - Sat, Jun 14

ORD

O'Hare Intl.

NAP

Naples Intl.

$1,291 Roundtrip, found 19 hours ago

$1,291

Roundtrip

found 19 hours ago

Select Air France flight, departing Fri, Jun 6 from O'Hare Intl. to Naples Intl., returning Sat, Jun 14, priced at $1,291 found 19 hours ago

Fri, Jun 6 - Sat, Jun 14

ORD

O'Hare Intl.

NAP

Naples Intl.

$1,336 Roundtrip, found 19 hours ago

$1,336

Roundtrip

found 19 hours ago

Select KLM flight, departing Fri, Jun 6 from O'Hare Intl. to Naples Intl., returning Sat, Jun 14, priced at $1,336 found 19 hours ago

Fri, Jun 6 - Sat, Jun 14

ORD

O'Hare Intl.

NAP

Naples Intl.

$1,359 Roundtrip, found 19 hours ago

$1,359

Roundtrip

found 19 hours ago

Select Austrian Airlines flight, departing Fri, Jun 6 from O'Hare Intl. to Naples Intl., returning Sat, Jun 14, priced at $1,359 found 19 hours ago

Thu, Jun 5 - Sun, Jun 15

ORD

O'Hare Intl.

NAP

Naples Intl.

$1,417 Roundtrip, found 19 hours ago

$1,417

Roundtrip

found 19 hours ago

Select American Airlines flight, departing Thu, Jun 5 from O'Hare Intl. to Naples Intl., returning Sun, Jun 15, priced at $1,417 found 19 hours ago

Fri, Jun 6 - Sat, Jun 14

ORD

O'Hare Intl.

NAP

Naples Intl.

$1,571 Roundtrip, found 19 hours ago

$1,571

Roundtrip

found 19 hours ago

Select British Airways flight, departing Fri, Jun 6 from O'Hare Intl. to Naples Intl., returning Sat, Jun 14, priced at $1,571 found 19 hours ago

Fri, Jun 6 - Sat, Jun 14

ORD

O'Hare Intl.

NAP

Naples Intl.

$1,892 Roundtrip, found 19 hours ago

$1,892

Roundtrip

found 19 hours ago

Select Aer Lingus flight, departing Fri, Jun 6 from O'Hare Intl. to Naples Intl., returning Sat, Jun 14, priced at $1,892 found 19 hours ago

Fri, Jun 6 - Sat, Jun 14

ORD

O'Hare Intl.

NAP

Naples Intl.

$1,920 Roundtrip, found 19 hours ago

$1,920

Roundtrip

found 19 hours ago

Select Iberia flight, departing Fri, Jun 6 from O'Hare Intl. to Naples Intl., returning Sat, Jun 14, priced at $1,920 found 19 hours ago