A grand cathedral with intricate Gothic architecture, a bustling square with historic buildings, and a clear sky.

CA $430 Cheap Flights from Chicago (CHI) to Milan (MIL)

View CA $430 flight on Sun, Nov 29, 2026

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    • Cheap Flights from Chicago to Milan (CHI-MIL)

    Prices were available within the past 7 days and start at CA $430 for one-way flights and CA $860 for roundtrip, for the period specified. Prices and availability are subject to change.

    All deals

    One way

    Roundtrip

    Select Condor flight, departing Thu, Sept 2 from Chicago to Milan, returning Thu, Sept 9, priced at CA $860 Found 1 day ago

    Thu, Sept 2 - Thu, Sept 9 · ORD · MXP · Roundtrip

    Select SAS flight, departing Sun, Jan 31 from Chicago to Milan, returning Fri, Feb 5, priced at CA $986 Found 3 days ago

    Sun, Jan 31 - Fri, Feb 5 · ORD · MXP · Roundtrip

    Select Air Serbia flight, departing Sat, Mar 20 from Chicago to Milan, returning Fri, Apr 2, priced at CA $1,061 Found 6 days ago

    Sat, Mar 20 - Fri, Apr 2 · ORD · MXP · Roundtrip

    Select Turkish Airlines flight, departing Mon, Jan 11 from Chicago to Milan, returning Tue, Mar 23, priced at CA $1,065 Found 1 day ago

    Mon, Jan 11 - Tue, Mar 23 · ORD · MXP · Roundtrip

    Select TAP Portugal flight, departing Fri, Mar 5 from Chicago to Milan, returning Tue, Mar 9, priced at CA $1,103 Found 3 days ago

    Fri, Mar 5 - Tue, Mar 9 · ORD · MXP · Roundtrip

    Select Delta flight, departing Tue, Aug 3 from Chicago to Milan, returning Fri, Aug 27, priced at CA $1,114 Found 6 days ago

    Tue, Aug 3 - Fri, Aug 27 · ORD · MXP · Roundtrip

    Select KLM flight, departing Tue, Aug 3 from Chicago to Milan, returning Fri, Aug 27, priced at CA $1,127 Found 6 days ago

    Tue, Aug 3 - Fri, Aug 27 · ORD · LIN · Roundtrip

    Select Virgin Atlantic flight, departing Mon, Jan 11 from Chicago to Milan, returning Tue, Mar 2, priced at CA $1,255 Found 1 day ago

    Mon, Jan 11 - Tue, Mar 2 · MDW · LIN · Roundtrip

    Select Delta flight, departing Sun, Dec 13 from Chicago to Milan, returning Thu, Dec 24, priced at CA $1,707 Found 3 days ago

    Sun, Dec 13 - Thu, Dec 24 · MDW · MXP · Roundtrip

    Select United flight, departing Mon, Sept 6 from Chicago to Milan, returning Mon, Sept 20, priced at CA $2,037 Found 4 days ago

    Mon, Sept 6 - Mon, Sept 20 · ORD · MXP · Roundtrip

    Alternative airports near Milan

    Prices were available within the past 7 days. Prices and availability are subject to change.

    Select flight to Malpensa Intl. MXP. Cheapest option available. Average driving time to city centre is 38 minutes. Flights from CA $1,077

    38 min

    Select flight to Linate LIN. Closest option available. Average driving time to city centre is 11 minutes. Flights from CA $1,224

    11 min

    Select flight to Orio Al Serio BGY. Average driving time to city centre is 41 minutes.

    41 min · Search flights

    Select flight to Guglielmo Marconi BLQ. Average driving time to city centre is 2 hours 6 minutes.

    2 h 6 min · Search flights

    Select flight to Turin Intl. TRN. Average driving time to city centre is 1 hour 26 minutes.

    1 h 26 min · Search flights

    Select flight to Cristoforo Colombo GOA. Average driving time to city centre is 1 hour 37 minutes.

    1 h 37 min · Search flights

    Select flight to Valerio Catullo VRN. Average driving time to city centre is 1 hour 39 minutes.

    1 h 39 min · Search flights

    Book with confidence

    Chicago to Milan Flights

    The easy way to book your flights from Chicago to Milan

    With Expedia, it’s simple to find and book flights to Milan from Chicago whether you’re traveling for business or pleasure. Enter your travel dates, hit search, and choose your flight from 13 airlines that cover this route. There are nonstop flights to MIL-All Airports, too.

    Choose your preferred carrier and cabin class with the advanced search tool and select your ideal departure time. Then, if you want, you can see just nonstop or refundable flights. And if you’re traveling last minute, just enter the date to check out flights from Chicago to Milan today, tomorrow, or this week.

    Save dollars with cheap flights from CHI-All Airports, CHI to MIL-All Airports, MIL

    Sort your search results by price to find great deals on your flight from Chicago to Milan—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Milan from Chicago currently is just CA $860 rising to CA $2,037.

    Here are more money-saving tips:

    • Fly in September when flight prices are normally at their lowest
    • Book about a month to 6 weeks before you travel for the best prices to Milan
    • Avoid peak season and weekends when flights can cost more
    • Early morning and late-night flights are sometimes cheaper, so try varying your travel times
    • One surefire way to save money on your flight is to book your flight and hotel together with Expedia. Sometimes, the savings are so large that the flight is basically free!

    Reasons to choose Expedia for your flight to Milan from Chicago

    Whatever your destination, budget, or reason to travel, in just one quick search, you can choose from loads of flights, airlines, and cabin classes. The filters make it quick and easy to find your ideal flights, and if you choose one of the flexible options, you won’t be charged to change your flight. So book your flight to Milan with Expedia today.

    Travel information

    Origin airportChicago Midway Airport
    Destination airportParma Airport
    Distance7,414 km away
    Roundtrip priceCA $860

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