American Airlines flights from Chicago to Milan

Recent searches for flights from Chicago to Milan

Sep 2026
From$1,744*
Updated: 9 hours ago
Round tripIEconomy
Oct 2026
From$832*
Updated: 9 hours ago
Round tripIEconomy
Nov 2026
From$782*
Updated: 9 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $1.3K
cmp-daily-histogram-bars-legend-max-price-aria-label $2.6K
Displaying fares for September-2026
  • ORD–MIL: cmp-view-offers-disclaimer. Find Offers
    03

    Th

    SEP

  • ORD–MXP, 09/04/26 – 09/11/26: From $2,491
    04

    Fr

  • ORD–MXP, 09/05/26 – 09/12/26: From $2,551
    05

    Sa

  • ORD–MXP, 09/06/26 – 09/13/26: From $2,501
    06

    Su

  • ORD–MXP, 09/07/26 – 09/14/26: From $2,491
    07

    Mo

  • ORD–MXP, 09/08/26 – 09/15/26: From $2,431
    08

    Tu

  • ORD–MXP, 09/09/26 – 09/16/26: From $2,431
    09

    We

  • ORD–MXP, 09/10/26 – 09/17/26: From $2,281
    10

    Th

  • ORD–MXP, 09/11/26 – 09/18/26: From $2,281
    11

    Fr

  • ORD–MXP, 09/12/26 – 09/19/26: From $2,334
    12

    Sa

  • ORD–MXP, 09/13/26 – 09/20/26: From $2,291
    13

    Su

  • ORD–MXP, 09/14/26 – 09/21/26: From $2,281
    14

    Mo

  • ORD–MXP, 09/15/26 – 09/22/26: From $2,221
    15

    Tu

  • ORD–MXP, 09/16/26 – 09/23/26: From $2,221
    16

    We

  • ORD–MXP, 09/17/26 – 09/24/26: From $1,811
    17

    Th

  • ORD–MXP, 09/18/26 – 09/25/26: From $1,811
    18

    Fr

  • ORD–MXP, 09/19/26 – 09/26/26: From $1,881
    19

    Sa

  • ORD–MXP, 09/20/26 – 09/27/26: From $1,804
    20

    Su

  • ORD–MXP, 09/21/26 – 09/28/26: From $1,811
    21

    Mo

  • ORD–MXP, 09/22/26 – 09/29/26: From $1,744
    22

    Tu

  • ORD–MXP, 09/23/26 – 09/30/26: From $1,744
    23

    We

  • ORD–MXP, 09/24/26 – 10/01/26: From $1,811
    24

    Th

  • ORD–MXP, 09/25/26 – 10/02/26: From $1,804
    25

    Fr

  • ORD–MXP, 09/26/26 – 10/03/26: From $1,864
    26

    Sa

  • ORD–MXP, 09/27/26 – 10/04/26: From $1,821
    27

    Su

  • ORD–MXP, 09/28/26 – 10/05/26: From $1,811
    28

    Mo

  • ORD–MXP, 09/29/26 – 10/06/26: From $1,751
    29

    Tu

  • ORD–MXP, 09/30/26 – 10/07/26: From $1,751
    30

    We

  • ORD–MXP, 10/01/26 – 10/08/26: From $1,320
    01

    Th

    OCT

  • ORD–MXP, 10/02/26 – 10/09/26: From $1,320
    02

    Fr

    • range$1,320-$2,551

    DisclaimerFares 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. To find the most updated fare, please visit aa.com. Fares listed may be Basic Economy, which class is subject to additional terms and conditions. Additional baggage fees and charges for optional products and services may apply.

    Find deals on Chicago to Milan flights

    $
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    Chicago (ORD)to

    Milan (MIL)
    11/03/26 - 11/10/26

    Round trip

    Economy

    from
    $855Fare subject to changes
    Updated: 5 hours ago

    Chicago (ORD)to

    Milan (MIL)
    11/02/26 - 11/07/26

    Round trip

    Economy

    from
    $1,510Fare subject to changes
    Updated: 5 hours ago

    Chicago (ORD)to

    Milan (MIL)
    10/04/26 - 10/08/26

    Round trip

    Economy

    from
    $2,134Fare subject to changes
    Updated: 1 hour ago

    Chicago (ORD)to

    Milan (MIL)
    10/09/26 - 10/12/26

    Round trip

    Economy

    from
    $1,038Fare subject to changes
    Updated: 16 hours ago

    Chicago (ORD)to

    Milan (MIL)
    03/19/27 - 03/29/27

    Round trip

    Economy

    from
    $1,211Fare subject to changes
    Updated: 23 hours 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.

    Finding cheap flights from Chicago to Milan

    Looking for lower fares on your trip from Chicago to Milan? Here are a few ways to save.

    • Book early: Booking 1 to 3 months ahead can help you find lower fares
    • Be flexible with dates: Midweek travel, like Tuesdays and Wednesdays, can be more affordable
    • Travel during less busy periods: Flying outside peak travel times can help find lower fares and avoid crowds

    Citi / AAdvantage credit card offer.

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    Make your trip more comfortable with Main Cabin Extra. Enjoy benefits like:

    • Extra legroom: More space with seats at the front of the Main Cabin or in exit rows.
    • Early boarding: Preferred Group 5 boarding allows easier access to overhead bins.
    • Complimentary drinks: Enjoy beer, wine and spirits on flights with full beverage service.

    Discover how Main Cabin Extra can enhance your trip.

    American Airlines flights from Chicago to Milan