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Flights from Chicago to Milan
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Book flight tickets from Chicago to Milan starting at ₹ 20,638

For as little as ₹ 20,638, you can take your next adventure to Milan without breaking the bank. Choose between one-way and return tickets from Chicago below.

  • One way
  • Round-trip
      • ORD22:00
        18h 25m
        1 stop
        MXP23:25
        Mon, Jan 13|Chicago - Milan|American Airlines
        ₹ 20,638₹ 26,884
        23% OFF
        23% OFF
        ₹ 26,884₹ 20,638

        Choose American Airlines flights from Chicago to Milan. The one-way connecting flight with American Airlines departs from O'Hare International Airport on Mon, Jan 13, arriving at Milan Malpensa Airport. One-way ticket prices start from ₹ 20,638 including taxes and charges.

      • ORD18:35
        16h 20m
        1 stop
        MXP17:55
        Wed, Jan 15|Chicago - Milan|American Airlines
        ₹ 20,696₹ 26,884
        23% OFF
        23% OFF
        ₹ 26,884₹ 20,696

        Choose American Airlines flights from Chicago to Milan. The one-way connecting flight with American Airlines departs from O'Hare International Airport on Wed, Jan 15, arriving at Milan Malpensa Airport. One-way ticket prices start from ₹ 20,696 including taxes and charges.

      • ORD18:45
        35h 45m
        1 stop
        MXP13:30
        Sat, Jan 18|Chicago - Milan|American Airlines
        ₹ 22,435₹ 26,884
        17% OFF
        17% OFF
        ₹ 26,884₹ 22,435

        Choose American Airlines flights from Chicago to Milan. The one-way connecting flight with American Airlines departs from O'Hare International Airport on Sat, Jan 18, arriving at Milan Malpensa Airport. One-way ticket prices start from ₹ 22,435 including taxes and charges.

      • ORD22:00
        18h 25m
        1 stop
        MXP23:25
        Mon, Jan 20|Chicago - Milan|American Airlines
        ₹ 22,808
        ₹ 22,808

        Choose American Airlines flights from Chicago to Milan. The one-way connecting flight with American Airlines departs from O'Hare International Airport on Mon, Jan 20, arriving at Milan Malpensa Airport. One-way ticket prices start from ₹ 22,808 including taxes and charges.

      • ORD18:35
        21h 50m
        1 stop
        MXP23:25
        Tue, Jan 28|Chicago - Milan|American Airlines
        ₹ 23,345
        ₹ 23,345

        Choose American Airlines flights from Chicago to Milan. The one-way connecting flight with American Airlines departs from O'Hare International Airport on Tue, Jan 28, arriving at Milan Malpensa Airport. One-way ticket prices start from ₹ 23,345 including taxes and charges.

      • ORD20:20
        34h 10m
        1 stop
        MXP13:30
        Sat, Jan 25|Chicago - Milan|American Airlines
        ₹ 23,368
        ₹ 23,368

        Choose American Airlines flights from Chicago to Milan. The one-way connecting flight with American Airlines departs from O'Hare International Airport on Sat, Jan 25, arriving at Milan Malpensa Airport. One-way ticket prices start from ₹ 23,368 including taxes and charges.

      • ORD22:00
        18h 30m
        1 stop
        MXP23:30
        Sun, Jan 12|Chicago - Milan|American Airlines
        ₹ 23,391
        ₹ 23,391

        Choose American Airlines flights from Chicago to Milan. The one-way connecting flight with American Airlines departs from O'Hare International Airport on Sun, Jan 12, arriving at Milan Malpensa Airport. One-way ticket prices start from ₹ 23,391 including taxes and charges.

      • ORD18:35
        21h 55m
        1 stop
        MXP23:30
        Wed, Feb 5|Chicago - Milan|American Airlines
        ₹ 23,671
        ₹ 23,671

        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 5, arriving at Milan Malpensa Airport. One-way ticket prices start from ₹ 23,671 including taxes and charges.

      • ORD11:40
        13h 30m
        1 stop
        MXP08:10
        Sun, Feb 2|Chicago - Milan|American Airlines
        ₹ 24,021
        ₹ 24,021

        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 2, arriving at Milan Malpensa Airport. One-way ticket prices start from ₹ 24,021 including taxes and charges.

      • ORD22:00
        18h 25m
        1 stop
        MXP23:25
        Fri, Jan 24|Chicago - Milan|American Airlines
        ₹ 24,465
        ₹ 24,465

        Choose American Airlines flights from Chicago to Milan. The one-way connecting flight with American Airlines departs from O'Hare International Airport on Fri, Jan 24, arriving at Milan Malpensa Airport. One-way ticket prices start from ₹ 24,465 including taxes and charges.

      • CHI01:00 pm
        3h 5m
        Nonstop
        MIL02:00 pm
        Tue, Dec 31|Chicago - Milan|American Airlines
        Find More Flights
        Find More Flights

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

Find the best time to fly from Chicago to Milan

These price trend charts carefully monitor and predict how flight prices from Chicago to Milan will change. Keep a close eye on them to understand when the best time to buy your tickets is.

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

Airlines Flying from Chicago to Milan

We have a range of prices from different airlines providing flights from Chicago to Milan. Check below for the journey which best suits your travel needs.

Icelandair
From ₹ 20,452
American Airlines
From ₹ 20,638
Jetblue Airways
From ₹ 24,231
United Airlines
From ₹ 25,410
Frontier Airlines
From ₹ 25,853
Lufthansa
From ₹ 28,361
TAP Air Portugal
From ₹ 29,295
Southwest Airlines
From ₹ 30,566
Air Serbia
From ₹ 31,301
Swiss
From ₹ 31,418

Find more flights and airlines

Alternative Routes from Chicago to Milan

Searching for potential routes that might be cheaper and faster? There are a few alternative ways to get to Milan from Chicago which could help you save money and time.

  • Cheapest
    Icelandair
    ORD
    18:30
    22h 0m
    2 transfer
    MXP
    23:30
    O'Hare International Airport - Milan Malpensa Airport
    Sun, Jan 12Icelandair
    ₹ 20,452
  • Icelandair
    ORD
    18:30
    35h 55m
    2 transfer
    LIN
    13:25
    O'Hare International Airport - Linate Airport
    Mon, Jan 13Icelandair
    ₹ 21,723
  • Icelandair
    ORD
    18:30
    34h 0m
    2 transfer
    BGY
    11:30
    O'Hare International Airport - Orio al Serio International Airport
    Mon, Jan 6Icelandair
    ₹ 23,216
  • Icelandair
    ORD
    18:30
    34h 0m
    2 transfer
    BGY
    11:30
    O'Hare International Airport - Orio al Serio International Airport
    Mon, Jan 6Icelandair
    ₹ 23,216
    Find More Flights

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 ₹ 88,922.

  • 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

If you leave it until the last minute and forget to check some of the key information when booking tickets, prices can often end up skyrocketing. Below, you can find our top tips for getting the best value flights – from changing dates to chasing deals, there are plenty ways to keep your next trip affordable.
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 price₹ 20,638
Off-season for travelOctober
Peak season for travelSeptember
Flight distance7,290.86 km
Popular airlineFinnair

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