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Popular Chicago to Italy flight itineraries

USD

  • Chicago (ORD)to

    Milan (MXP)
    14/05/2025 - 21/05/2025
    from
    $1,421Fare subject to changes
    Updated: 14 hours ago
    Round trip
    I
    Economy

    Chicago (ORD)to

    Bologna (BLQ)
    23/04/2025 - 30/04/2025
    from
    $793Fare subject to changes
    Updated: 4 hours ago
    Round trip
    I
    Economy

    Chicago (CHI)to

    Venice (VCE)
    07/05/2025 - 14/05/2025
    from
    $721Fare subject to changes
    Updated: 13 hours ago
    Round trip
    I
    Economy

    Chicago (ORD)to

    Milan (LIN)
    29/04/2025 - 15/05/2025
    from
    $1,586Fare subject to changes
    Updated: 10 hours ago
    Round trip
    I
    Economy

*Fares displayed have been collected within the last 24hrs and may no longer be available at time of booking. Modifying this information may result in a different fare. Additional bag and optional fees for products and services may apply.

Find more  Chicago to Italy deals

USD
Find more  Chicago to Italy deals
From
To
Fare type
Travel dates
Price
Chicago (ORD)Rome (FCO)Round trip
I
Economy		20/01/2026 - 25/02/2026

from

$493Fare subject to changes

Updated: 12 hours ago

Chicago (ORD)Naples (NAP)Round trip
I
Economy		26/12/2025 - 03/01/2026

from

$3,153Fare subject to changes

Updated: 10 hours ago

Chicago (CHI)Rome (ROM)Round trip
I
Economy		09/11/2025 - 19/11/2025

from

$498Fare subject to changes

Updated: 15 hours ago

Chicago (ORD)Milan (MXP)Round trip
I
Economy		13/11/2025 - 19/11/2025

from

$933Fare subject to changes

Updated: 13 hours ago

Chicago (CHI)Venice (VCE)Round trip
I
Economy		28/10/2025 - 04/11/2025

from

$621Fare subject to changes

Updated: 1 hour ago

*Fares displayed have been collected within the last 24hrs and may no longer be available at time of booking. Some fares listed may include one or more connections that are Basic Economy, which class is subject to additional terms and conditions. Modifying this information may result in a different fare. To find the most updated fare, please visit aa.com. Additional baggage fees and charges for optional products and services may apply.

American Airlines flights from Chicago to Italy

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From
To
Fare type
Travel dates
Price
Chicago (ORD)Rome (FCO)Round trip
I
Economy		22/04/2025 - 29/04/2025

from

$574Fare subject to changes

Updated: 14 hours ago

Chicago (ORD)Naples (NAP)Round trip
I
Economy		04/10/2025 - 23/10/2025

from

$797Fare subject to changes

Updated: 23 hours ago

Chicago (CHI)Rome (ROM)Round trip
I
Economy		22/04/2025 - 29/04/2025

from

$574Fare subject to changes

Updated: 16 hours ago

Chicago (ORD)Venice (VCE)Round trip
I
Economy		06/05/2025 - 13/05/2025

from

$721Fare subject to changes

Updated: 8 hours ago

Chicago (ORD)Milan (MXP)Round trip
I
Economy		27/05/2025 - 03/06/2025

from

$1,026Fare subject to changes

Updated: 14 hours ago

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From
To
Fare type
Travel dates
Price
Booking
Chicago (ORD)London (LHR)Round trip
I
Premium Economy		20/10/2025 - 06/11/2025

from

$1,485Fare subject to changes

Updated: 59 minutes ago

Chicago (ORD)Athens (ATH)Round trip
I
Premium Economy		20/04/2025 - 27/04/2025

from

$2,261Fare subject to changes

Updated: 14 hours ago

Chicago (ORD)Rome (FCO)Round trip
I
Premium Economy		20/10/2025 - 04/11/2025

from

$1,443Fare subject to changes

Updated: 2 hours ago

Chicago (ORD)Madrid (MAD)Round trip
I
Premium Economy		28/09/2025 - 07/10/2025

from

$1,288Fare subject to changes

Updated: 12 hours ago

Chicago (ORD)Tokyo (TYO)Round trip
I
Premium Economy		27/09/2025 - 11/10/2025

from

$3,412Fare subject to changes

Updated: 3 hours ago

Chicago (ORD)Paris (CDG)Round trip
I
Premium Economy		18/08/2025 - 08/09/2025

from

$1,561Fare subject to changes

Updated: 9 hours ago

Chicago (ORD)Dublin (DUB)Round trip
I
Premium Economy		14/10/2025 - 22/10/2025

from

$1,679Fare subject to changes

Updated: 6 hours ago

Chicago (ORD)Honolulu (HNL)Round trip
I
Premium Economy		12/09/2025 - 29/09/2025

from

$1,861Fare subject to changes

Updated: 12 hours ago

Chicago (ORD)Barcelona (BCN)Round trip
I
Premium Economy		18/08/2025 - 18/09/2025

from

$1,770Fare subject to changes

Updated: 10 hours ago

Chicago (ORD)Tokyo (HND)Round trip
I
Premium Economy		06/10/2025 - 16/10/2025

from

$4,086Fare subject to changes

Updated: 8 hours ago

Chicago (ORD)Maui (OGG)Round trip
I
Premium Economy		15/10/2025 - 22/10/2025

from

$1,991Fare subject to changes

Updated: 2 hours ago

Chicago (ORD)London (LON)Round trip
I
Premium Economy		11/08/2025 - 26/08/2025

from

$1,687Fare subject to changes

Updated: 14 hours ago

Chicago (ORD)Naples (NAP)Round trip
I
Premium Economy		18/08/2025 - 31/08/2025

from

$1,855Fare subject to changes

Updated: 4 hours ago

Chicago (ORD)Lisbon (LIS)Round trip
I
Premium Economy		18/08/2025 - 25/08/2025

from

$1,693Fare subject to changes

Updated: 3 hours ago

Chicago (ORD)Sydney (SYD)Round trip
I
Premium Economy		09/06/2025 - 23/06/2025

from

$3,815Fare subject to changes

Updated: 16 hours ago

Chicago (ORD)Kauai (LIH)Round trip
I
Premium Economy		11/05/2025 - 16/05/2025

from

$2,115Fare subject to changes

Updated: 5 hours ago

Chicago (ORD)Bangkok (BKK)Round trip
I
Premium Economy		13/10/2025 - 19/10/2025

from

$2,996Fare subject to changes

Updated: 12 hours ago

Chicago (ORD)Shanghai (PVG)Round trip
I
Premium Economy		02/07/2025 - 23/07/2025

from

$3,075Fare subject to changes

Updated: 8 hours ago

Chicago (CHI)London (LON)Round trip
I
Premium Economy		09/08/2025 - 21/08/2025

from

$1,588Fare subject to changes

Updated: 5 hours ago

Chicago (ORD)Zurich (ZRH)Round trip
I
Premium Economy		22/08/2025 - 31/08/2025

from

$1,859Fare subject to changes

Updated: 8 hours ago

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