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Flights from Chicago to Milan
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Flights from Chicago to Milan Starting at NZD 442

We've found these cheap flights for you. You can book one-way or return flight tickets.

  • One way
  • Round-trip
      • Cheapest nonstop
        ORD21:35
        8h 45m
        Nonstop
        MXP13:20
        Tue, Apr 8|Chicago - Milan|United Airlines
        NZD 1,448NZD 1,766
        18% OFF
        18% OFF
        NZD 1,766NZD 1,448

        Choose United Airlines flights from Chicago to Milan. The one-way direct flight with United Airlines departs from O'Hare International Airport on Tue, Apr 8, arriving at Milan Malpensa Airport. One-way Prices start from NZD 1,448 including taxes and charges.

      • ORD21:15
        17h 40m
        1 stop
        MXP20:55
        Tue, Mar 25|Chicago - Milan|American Airlines
        NZD 442NZD 1,766
        75% OFF
        75% OFF
        NZD 1,766NZD 442

        Choose American Airlines flights from Chicago to Milan. The one-way connecting flight with American Airlines departs from O'Hare International Airport on Tue, Mar 25, arriving at Milan Malpensa Airport. One-way Prices start from NZD 442 including taxes and charges.

      • ORD19:30
        21h 55m
        1 stop
        MXP23:25
        Mon, Mar 10|Chicago - Milan|American Airlines
        NZD 452NZD 1,766
        74% OFF
        74% OFF
        NZD 1,766NZD 452

        Choose American Airlines flights from Chicago to Milan. The one-way connecting flight with American Airlines departs from O'Hare International Airport on Mon, Mar 10, arriving at Milan Malpensa Airport. One-way Prices start from NZD 452 including taxes and charges.

      • ORD21:55
        13h 30m
        1 stop
        MXP18:25
        Sun, Mar 30|Chicago - Milan|American Airlines
        NZD 454
        NZD 454

        Choose American Airlines flights from Chicago to Milan. The one-way connecting flight with American Airlines departs from O'Hare International Airport on Sun, Mar 30, arriving at Milan Malpensa Airport. One-way Prices start from NZD 454 including taxes and charges.

      • ORD21:56
        30h 39m
        1 stop
        MXP11:35
        Sun, Feb 16|Chicago - Milan|American Airlines
        NZD 464
        NZD 464

        Choose American Airlines flights from Chicago to Milan. The one-way connecting flight with American Airlines departs from O'Hare International Airport on Sun, Feb 16, arriving at Milan Malpensa Airport. One-way Prices start from NZD 464 including taxes and charges.

      • ORD20:25
        20h 5m
        1 stop
        MXP23:30
        Sun, Feb 23|Chicago - Milan|American Airlines
        NZD 478
        NZD 478

        Choose American Airlines flights from Chicago to Milan. The one-way connecting flight with American Airlines departs from O'Hare International Airport on Sun, Feb 23, arriving at Milan Malpensa Airport. One-way Prices start from NZD 478 including taxes and charges.

      • ORD18:26
        22h 4m
        1 stop
        MXP23:30
        Wed, Feb 19|Chicago - Milan|American Airlines
        NZD 485
        NZD 485

        Choose American Airlines flights from Chicago to Milan. The one-way connecting flight with American Airlines departs from O'Hare International Airport on Wed, Feb 19, arriving at Milan Malpensa Airport. One-way Prices start from NZD 485 including taxes and charges.

      • ORD18:26
        18h 44m
        1 stop
        MXP20:10
        Mon, Feb 17|Chicago - Milan|American Airlines
        NZD 486
        NZD 486

        Choose American Airlines flights from Chicago to Milan. The one-way connecting flight with American Airlines departs from O'Hare International Airport on Mon, Feb 17, arriving at Milan Malpensa Airport. One-way Prices start from NZD 486 including taxes and charges.

      • ORD17:50
        22h 20m
        1 stop
        MXP23:10
        Mon, Apr 7|Chicago - Milan|American Airlines
        NZD 488
        NZD 488

        Choose American Airlines flights from Chicago to Milan. The one-way connecting flight with American Airlines departs from O'Hare International Airport on Mon, Apr 7, arriving at Milan Malpensa Airport. One-way Prices start from NZD 488 including taxes and charges.

      • ORD17:50
        22h 30m
        1 stop
        MXP23:20
        Tue, Apr 29|Chicago - Milan|American Airlines
        NZD 497
        NZD 497

        Choose American Airlines flights from Chicago to Milan. The one-way connecting flight with American Airlines departs from O'Hare International Airport on Tue, Apr 29, arriving at Milan Malpensa Airport. One-way Prices start from NZD 497 including taxes and charges.

      • CHI01:00 pm
        3h 5m
        Nonstop
        MIL02:00 pm
        Tue, Feb 18|Chicago - Milan|United Airlines
        Find More Flights
        Find More Flights

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Chicago to Milan flight time & flight schedules

Flight info.
Departure
Arrival
Weekly Schedule

  1. UA399

    United Airlines

    11:20

    ORD

    2.4h

    14:46

    BOS

    SMTWTFS
    Search

  2. UA8363

    United Airlines

    18:45

    BOS

    1.3h

    20:00

    YUL

    -----F-

  3. UA8060

    United Airlines

    20:10

    YUL

    7.8h

    10:00

    MXP

    S-T--F-

  4. AA2840

    American Airlines

    14:52

    ORD

    2.0h

    17:55

    PHL

    SMTWTFS
    Search

  5. AA754

    American Airlines

    22:05

    PHL

    7.4h

    11:30

    CDG

    SMTWTFS

  6. U23814

    easyJet

    22:55

    CDG

    1.5h

    00:25

    MXP

    SMTWT-S

  7. KL612

    KLM

    16:20

    ORD

    7.8h

    07:05

    AMS

    S-T-T-S
    Search

  8. KL1615

    KLM

    14:15

    AMS

    1.7h

    15:55

    LIN

    SMTWTFS

  9. IB342

    Iberia

    16:30

    ORD

    8.4h

    07:55

    MAD

    SMTW-FS
    Search

  10. IB673

    Iberia

    12:00

    MAD

    2.2h

    14:10

    MXP

    SMTWT--

  11. AF137

    Air France

    17:10

    ORD

    8.0h

    08:10

    CDG

    SM-WTF-
    Search

  12. U24541

    easyJet

    06:30

    CDG

    1.5h

    08:00

    MXP

    SMT-TFS

  13. TP244

    TAP Air Portugal

    18:00

    ORD

    8.0h

    08:00

    LIS

    --T---S
    Search

  14. TP826

    TAP Air Portugal

    13:10

    LIS

    2.8h

    16:55

    MXP

    SMTWTFS

  15. SK944

    Scandinavian Airlines

    19:15

    ORD

    8.5h

    10:45

    CPH

    S--WTFS
    Search

  16. SK687

    Scandinavian Airlines

    17:10

    CPH

    2.1h

    19:15

    MXP

    SMTWTFS

  17. FI852

    Icelandair

    19:25

    ORD

    6.3h

    06:40

    KEF

    SMTWTFS
    Search

  18. FI542

    Icelandair

    07:35

    KEF

    3.4h

    13:00

    CDG

    SMTWTFS

  19. U23810

    easyJet

    13:45

    CDG

    1.5h

    15:15

    MXP

    --TW--S

  20. FI852

    Icelandair

    19:25

    ORD

    6.3h

    06:40

    KEF

    SMTWTFS
    Search

  21. FI590

    Icelandair

    08:20

    KEF

    4.2h

    14:30

    MXP

    ---W--S

  22. LO004

    LOT Polish Airlines

    21:55

    ORD

    8.9h

    13:50

    WAW

    SMTWTF-
    Search

  23. LO319

    LOT Polish Airlines

    16:40

    WAW

    2.3h

    18:55

    MXP

    SMTWTFS
Find more flights and airlines

Find the best time to fly from Chicago to Milan

We monitor flight fares to help you find the best deals effortlessly

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

Airlines Flying from Chicago to Milan

Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.
TAP Air Portugal logoTAP Air PortugalTurkish Airlines logoTurkish Airlines

FAQ

  • When are flight tickets from Chicago (CHI) to Milan (MIL) the cheapest?

    Airlines adjust prices for flights from Chicago to Milan based on the departure date and time of your selection. By analyzing data from all airlines, we've discovered that on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.

  • How much do flights from Chicago (CHI) to Milan (MIL) cost?

    According to Trip.com's data, the lowest price is around NZD 1,851.

  • What is the transportation method from the main airport to downtown in Milan?

    • The distance from Milan Malpensa Airport to downtown is about 40 km. It takes about 1 hour by taxi.
    • The distance from Linate Airport to downtown is about 7 km. It takes about 20 minutes by taxi.
    • The distance from Orio al Serio International Airport to downtown is about 46 km. It takes about 1 hour by taxi.

How to find a cheap flight from Chicago to Milan

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Chicago to Milan. Book your flights at the right time and save more.
1
Book Early
Once prices are gone, they're gone. Lock in deals while you can!
2
Compare Flight Prices
Compare prices on travel agency and airline websites.
3
Look Out for Deals
Check airline and travel agency websites for latest flight deals
4
Check One-way Fares
Buying two cheap one-way flights can sometimes be a better deal than a round-trip.
5
Try Different Dates
Flying during the week, early in the morning, or late at night can help save money.
6
Use the Trip.com App
Save up to £10 per person when booking your flights on Trip.com

Flight Information from Chicago to Milan

Cheapest nonstop flight priceNZD 442
Cheapest round-trip ticket priceNZD 1,515
Off-season for travelJanuary
Peak season for travelMay
Flight distance7,290.86 km
Popular airlineDelta Air Lines

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