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Flights from Chicago to Milan
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Latest Flight Deals from Chicago to Milan

Book one-way or return flights from Chicago to Milan from as little as £204. Choose from the popular airlines below and book your flight today!

  • One way
  • Round-trip
      • ORD21:00
        16h 10m
        1 stop
        MXP20:10
        Mon, Jul 15|Chicago - Milan|American Airlines
        £204£298
        32% OFF
        32% OFF
        £298£204
      • ORD21:00
        27h 55m
        1 stop
        LIN07:55
        Tue, Jul 9|Chicago - Milan|American Airlines
        £205£298
        31% OFF
        31% OFF
        £298£205
      • ORD21:00
        14h 55m
        1 stop
        LIN18:55
        Sun, Aug 4|Chicago - Milan|American Airlines
        £208£298
        30% OFF
        30% OFF
        £298£208
      • ORD20:40
        15h 15m
        1 stop
        LIN18:55
        Wed, Aug 14|Chicago - Milan|American Airlines
        £217
        £217
      • ORD21:00
        19h 10m
        1 stop
        MXP23:10
        Tue, Jul 16|Chicago - Milan|American Airlines
        £218
        £218
      • ORD21:00
        27h 55m
        1 stop
        LIN07:55
        Wed, Jul 17|Chicago - Milan|American Airlines
        £218
        £218
      • ORD22:45
        17h 40m
        1 stop
        MXP23:25
        Wed, Jul 10|Chicago - Milan|American Airlines
        £228
        £228
      • ORD21:00
        19h 10m
        1 stop
        MXP23:10
        Tue, Jul 23|Chicago - Milan|American Airlines
        £229
        £229
      • ORD20:40
        29h
        1 stop
        MXP08:40
        Mon, Aug 19|Chicago - Milan|American Airlines
        £230
        £230
      • ORD20:40
        15h 50m
        1 stop
        MXP19:30
        Tue, Aug 20|Chicago - Milan|American Airlines
        £230
        £230
      • CHI13:00
        3h 5m
        Direct
        MIL14:00
        Thu, Jul 4|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.

Searching for the best last minute flight from Chicago to Milan? Find one-way or return flights that are affordable and fit your itinerary.

Trip.com monitors the ticket fares of flights from Chicago to Milan. Stay updated on price trends and snag the best deals for your upcoming trip.

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.
Airlines Flying from Chicago to Milan

View airlines operating flights from Chicago to Milan. Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.

American Airlines
From £194
Icelandair
From £195
TAP Air Portugal
From £197
Jetblue Airways
From £230
Frontier Airlines
From £240
Spirit Airlines
From £241
United Airlines
From £260
Alaska Airlines
From £262
Virgin Atlantic
From £348
Scandinavian Airlines
From £360
ANA airlines

Find more flights and airlines

Alternative Routes from Chicago to Milan

Discover different routes, airlines, and transfers and find the best alternative flights for your journey from Chicago to Milan.

  • Cheapest
    American Airlines
    ORD
    20:40
    29h 10m
    1 transfer
    MXP
    08:50
    O'Hare International Airport - Milan Malpensa Airport
    Sun, Aug 18American Airlines
    £194
  • Icelandair
    ORD
    22:15
    28h 45m
    2 transfer
    LIN
    10:00
    O'Hare International Airport - Linate Airport
    Sun, Aug 18Icelandair
    £195
  • American Airlines
    ORD
    17:15
    12h 15m
    1 transfer
    BGY
    12:30
    O'Hare International Airport - Orio al Serio International Airport
    Mon, Jul 22American Airlines
    £236
  • American Airlines
    ORD
    17:15
    12h 15m
    1 transfer
    BGY
    12:30
    O'Hare International Airport - Orio al Serio International Airport
    Mon, Jul 22American Airlines
    £236
    Find More Flights

How do I find the cheapest flights?

  • 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 £1,103.

  • How long does it take to fly from Chicago (CHI) to Milan (MIL) and what is the distance?

    It takes around 8 hours 45 minutes to fly from Chicago (CHI) to Milan (MIL).

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

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

  • What are the most popular airlines that fly from Chicago (CHI) to Milan (MIL)?

    Airlines with flights from Chicago (CHI) to Milan (MIL): Air Canada, United Airlines, Austrian Airlines, Brussels Airlines and Swiss.

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 price

£203

Cheapest round-trip ticket price

£686

Off-season for travel

April

Peak season for travel

December

Flight distance

7,290.86km

Average flight time

8 hours 45 minutes

Popular airline

Finnair

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