Flights from Chicago to Milan available from USD 1,279*

Promo code

Our best rates from Chicago to Milan

Jul 2026
FromUSD 1,773*
Fare: Round trip/Economy
Aug 2026
Looks like you're the first to search this route on these dates
Sep 2026
FromUSD 1,279*
Fare: Round trip/Economy
Displaying fares for June-2026
  • 01

    We

    JUL

  • 02

    Th

  • 03

    Fr

  • 04

    Sa

  • 05

    Su

  • 06

    Mo

  • 07

    Tu

  • 08

    We

  • 09

    Th

  • 10

    Fr

  • 11

    Sa

  • 12

    Su

  • 13

    Mo

  • 14

    Tu

  • 15

    We

  • 16

    Th

  • 17

    Fr

  • 18

    Sa

  • 19

    Su

  • 20

    Mo

  • 21

    Tu

  • 22

    We

  • 23

    Th

  • 24

    Fr

  • 25

    Sa

  • 26

    Su

  • 27

    Mo

  • 28

    Tu

  • 29

    We

  • 30

    Th

  • 31

    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 three months: flights from Chicago to Milan

    USD

    Chicago (ORD)to

    Milan (MXP)
    Sep 03 2026 - Sep 24 2026
    From
    USD 1,279
    Round trip
    Economy

    Chicago (ORD)to

    Milan (MXP)
    Jul 02 2026 - Jul 09 2026
    From
    USD 1,773
    Round trip
    Economy

    *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.

     

    Plan ahead for your trip from Chicago to Milan with Icelandair

    USD

    *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.

    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!