American Airlines flights from Chicago to Milan

Recent searches for flights from Chicago to Milan

Aug 2026
From$792*
Updated: 8 hours ago
Round tripIEconomy
Sep 2026
From$834*
Updated: 8 hours ago
Round tripIEconomy
Oct 2026
From$812*
Updated: 8 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $792
cmp-daily-histogram-bars-legend-max-price-aria-label $1.9K
Displaying fares for August-2026
  • ORD–MIL: cmp-view-offers-disclaimer. Find Offers
    14

    Fr

    AUG

  • ORD–MXP, 08/15/26 – 08/22/26: From $897
    15

    Sa

  • ORD–MXP, 08/16/26 – 08/23/26: From $847
    16

    Su

  • ORD–MXP, 08/17/26 – 08/24/26: From $842
    17

    Mo

  • ORD–MXP, 08/18/26 – 08/25/26: From $792
    18

    Tu

  • ORD–MXP, 08/19/26 – 08/26/26: From $792
    19

    We

  • ORD–MXP, 08/20/26 – 08/27/26: From $834
    20

    Th

  • ORD–MXP, 08/21/26 – 08/28/26: From $834
    21

    Fr

  • ORD–MXP, 08/22/26 – 08/29/26: From $892
    22

    Sa

  • ORD–MXP, 08/23/26 – 08/30/26: From $850
    23

    Su

  • ORD–MXP, 08/24/26 – 08/31/26: From $842
    24

    Mo

  • ORD–MXP, 08/25/26 – 09/01/26: From $1,507
    25

    Tu

  • ORD–MXP, 08/26/26 – 09/02/26: From $1,499
    26

    We

  • ORD–MXP, 08/27/26 – 09/03/26: From $1,820
    27

    Th

  • ORD–MXP, 08/28/26 – 09/04/26: From $1,472
    28

    Fr

  • ORD–MXP, 08/29/26 – 09/05/26: From $1,720
    29

    Sa

  • ORD–MXP, 08/30/26 – 09/06/26: From $1,712
    30

    Su

  • ORD–MXP, 08/31/26 – 09/07/26: From $1,739
    31

    Mo

  • ORD–MXP, 09/01/26 – 09/08/26: From $1,752
    01

    Tu

    SEP

  • ORD–MXP, 09/02/26 – 09/09/26: From $1,778
    02

    We

  • ORD–MXP, 09/03/26 – 09/10/26: From $1,849
    03

    Th

  • ORD–MXP, 09/04/26 – 09/11/26: From $1,803
    04

    Fr

  • ORD–MXP, 09/05/26 – 09/12/26: From $1,898
    05

    Sa

  • ORD–MXP, 09/06/26 – 09/13/26: From $1,812
    06

    Su

  • ORD–MXP, 09/07/26 – 09/14/26: From $1,812
    07

    Mo

  • ORD–MXP, 09/08/26 – 09/15/26: From $1,743
    08

    Tu

  • ORD–MXP, 09/09/26 – 09/16/26: From $1,760
    09

    We

  • ORD–MXP, 09/10/26 – 09/17/26: From $1,803
    10

    Th

  • ORD–MXP, 09/11/26 – 09/18/26: From $1,362
    11

    Fr

  • ORD–MXP, 09/12/26 – 09/19/26: From $1,505
    12

    Sa

  • ORD–MXP, 09/13/26 – 09/20/26: From $1,062
    13

    Su

    • range$792-$1,898

    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

    $
    keyboard_arrow_down

    Chicago (ORD)to

    Milan (MIL)
    10/21/26 - 10/28/26

    Round trip

    Economy

    from
    $949Fare subject to changes
    Updated: 12 hours ago

    Chicago (ORD)to

    Milan (MIL)
    10/09/26 - 10/18/26

    Round trip

    Economy

    from
    $963Fare subject to changes
    Updated: 23 hours ago

    Chicago (ORD)to

    Milan (MIL)
    10/03/26 - 10/09/26

    Round trip

    Economy

    from
    $965Fare subject to changes
    Updated: 14 hours ago

    Chicago (ORD)to

    Milan (MIL)
    09/14/26 - 09/21/26

    Round trip

    Economy

    from
    $1,004Fare subject to changes
    Updated: 23 hours ago

    Chicago (ORD)to

    Milan (MIL)
    11/20/26 - 11/28/26

    Round trip

    Economy

    from
    $1,190Fare subject to changes
    Updated: 21 hours ago

    Chicago (ORD)to

    Milan (MIL)
    10/04/26 - 10/09/26

    Round trip

    Economy

    from
    $2,133Fare subject to changes
    Updated: 14 hours ago

    Chicago (ORD)to

    Milan (MIL)
    10/14/26 - 10/24/26

    Round trip

    Economy

    from
    $875Fare subject to changes
    Updated: 1 hour ago

    Chicago (ORD)to

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

    Round trip

    Economy

    from
    $954Fare subject to changes
    Updated: 21 minutes 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

    Earn up to $500 back on your next American Airlines flight plus, 30,000 bonus miles. Offers vary elsewhere. Opens another site in a new window that may not meet accessibility guidelines.

    Upgrade your flight with Main Cabin Extra

    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