Flights from Chicago to Milan available from USD 626*

Promo code

Our best rates from Chicago to Milan

Aug 2026
FromUSD 1,170*
Fare: Round trip/Economy
Sep 2026
FromUSD 633*
Fare: Round trip/Economy
Oct 2026
FromUSD 626*
Fare: Round trip/Economy
Displaying fares for August-2026
  • ORD–MXP, Aug 26 2026 – Aug 30 2026: From USD 1,378
    26

    We

    AUG

  • ORD–MXP, Aug 27 2026 – Aug 30 2026: From USD 1,573
    27

    Th

  • ORD–MXP, Aug 28 2026 – Aug 30 2026: From USD 1,573
    28

    Fr

  • ORD–MXP, Aug 29 2026 – Sep 05 2026: From USD 1,573
    29

    Sa

  • ORD–MXP, Aug 30 2026 – Sep 05 2026: From USD 1,523
    30

    Su

  • ORD–MXP, Aug 31 2026 – Sep 05 2026: From USD 1,170
    31

    Mo

  • ORD–MXP, Sep 01 2026 – Sep 15 2026: From USD 1,953
    01

    Tu

    SEP

  • ORD–MXP, Sep 02 2026 – Sep 07 2026: From USD 2,656
    02

    We

  • ORD–MXP, Sep 03 2026 – Sep 07 2026: From USD 1,574
    03

    Th

  • ORD–MXP, Sep 04 2026 – Sep 24 2026: From USD 1,576
    04

    Fr

  • ORD–MXP, Sep 05 2026 – Sep 24 2026: From USD 948
    05

    Sa

  • ORD–MXP, Sep 06 2026 – Sep 15 2026: From USD 1,116
    06

    Su

  • ORD–MXP, Sep 07 2026 – Sep 29 2026: From USD 871
    07

    Mo

  • ORD–MXP, Sep 08 2026 – Sep 24 2026: From USD 1,118
    08

    Tu

  • ORD–MXP, Sep 09 2026 – Sep 15 2026: From USD 871
    09

    We

  • ORD–MXP, Sep 10 2026 – Oct 11 2026: From USD 862
    10

    Th

  • ORD–MXP, Sep 11 2026 – Oct 11 2026: From USD 937
    11

    Fr

  • ORD–MXP, Sep 12 2026 – Oct 11 2026: From USD 864
    12

    Sa

  • ORD–MXP, Sep 13 2026 – Oct 11 2026: From USD 862
    13

    Su

  • ORD–MXP, Sep 14 2026 – Oct 11 2026: From USD 937
    14

    Mo

  • ORD–MXP: cmp-view-offers-disclaimer. Find offers
    15

    Tu

  • ORD–MXP, Sep 16 2026 – Oct 11 2026: From USD 862
    16

    We

  • ORD–MXP: cmp-view-offers-disclaimer. Find offers
    17

    Th

  • ORD–MXP, Sep 18 2026 – Oct 11 2026: From USD 862
    18

    Fr

  • ORD–MXP, Sep 19 2026 – Oct 18 2026: From USD 1,157
    19

    Sa

  • ORD–MXP, Sep 20 2026 – Oct 11 2026: From USD 1,077
    20

    Su

  • ORD–MXP, Sep 21 2026 – Oct 11 2026: From USD 708
    21

    Mo

  • ORD–MXP: cmp-view-offers-disclaimer. Find offers
    22

    Tu

  • ORD–MXP, Sep 23 2026 – Oct 11 2026: From USD 633
    23

    We

  • ORD–MXP: cmp-view-offers-disclaimer. Find offers
    24

    Th

  • ORD–MXP, Sep 25 2026 – Oct 11 2026: From USD 635
    25

    Fr

    • *Fares displayed have been collected within the last 72hrs and may no longer be available at the time of booking

    Fly in the next 3 months: flights from Chicago to Milan (MXP)

    USD

    Chicago (ORD)to

    Milan (MXP)
    Oct 02 2026 - Oct 11 2026
    From
    USD 626
    Viewed 13 hrs ago
    Round trip
    Economy

    Chicago (ORD)to

    Milan (MXP)
    Oct 05 2026 - Oct 18 2026
    From
    USD 626
    Viewed 13 hrs ago
    Round trip
    Economy
    *Fares displayed have been collected within the last 72 hours and may no longer be available at the time of booking. We display fares for Economy Light as standard, but it is possible to change your class of service during the booking process. You can also add baggage meals and extra legroom to your trip during booking.

    Flights from Chicago (ORD) to Milan (MXP) in the next 365 days

    Book ahead and find our best prices in 2026 and beyond

    USD
    Flights from Chicago (ORD) to Milan (MXP) in the next 365 days
    From
    To
    Fare type
    Dates
    Price
    Chicago (ORD)Milan (MXP)Round trip
    /
    Economy    		Oct 02 2026 - Oct 11 2026

    From

    USD 626

    Viewed 13 hrs ago

    Chicago (ORD)Milan (MXP)Round trip
    /
    Economy    		Oct 05 2026 - Oct 18 2026

    From

    USD 626

    Viewed 13 hrs ago

    Chicago (ORD)Milan (MXP)Round trip
    /
    Economy    		Oct 07 2026 - Oct 11 2026

    From

    USD 626

    Viewed 13 hrs ago

    *Fares displayed have been collected within the last 72hrs and may no longer be available at the time of booking. We display fares for Economy Light as standard but it is possible to change your class of service during the booking process. You can also add baggage, meals and extra legroom to your trip during booking.

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    Flights from Chicago (ORD) to Milan (MXP)

    Choose Icelandair to fly from Chicago (ORD) to Milan (MXP). Enjoy our refreshing travel experience, which includes hundreds of hours of movies and music in our in-seat entertainment system, USB chargers in every seat and Wi-Fi access. You'll enjoy an easy transit at our Keflavik hub and one of the shortest flying times between North America and Europe.

    Looking for a flight from Chicago to the capital of Italy's Lombardy region? If you book your plane tickets to Europe with Icelandair, you can add a stopover in Iceland to your travel plans. You can make your stopover anything from 1 to 7 days, and you will have the opportunity to explore Iceland's geyser, waterfalls and caves, and to visit the charming capital of Reykjavik. Then, you can catch the plane to your final destination and take in the exquisite Duomo cathedral and explore the museums and exhibitions of the medieval Castello Sforzesco!

    Flying with Icelandair: more than just a journey