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$314+ Cheap flights from Milan (MIL) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/17. Fares are subject to change and may not be available on all flights or dates of travel.
MIL — CHI
Aug 18 — Aug 251
Mon 8/18
Mon 8/25
1 adult, Economy
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Cheapflights Tip: The best prices from Milan to Chicago are usually found in November or February, booked 13 days in advance, depart on a Tuesday or Wednesday and return on a Tuesday

Cheap flight deals from Milan to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Milan (MIL) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 13, 2025.

Round-trip from

$582
(Mytrip)

One-way from

$314
(Trip.com)

Popular in

July

Cheapest in

November

Average price

$827

Good round-trip deal

$907 or less

Good one-way deal

$733 or less
From Milan (MIL) to Chicago (CHI)
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One-way flight from Milan (MIL) to Chicago (CHI)
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Highest demand for flights based on searches. 18% potential increase in price ($154 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($23 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Milan (MIL) to Chicago (CHI).
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Price to beat on a one-way flight from Milan (MIL) to Chicago (CHI).
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Find flight deals from Milan to Chicago

Cheapest flights from Milan to Chicago
Explore the most affordable flight options available from Milan to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 13, 2025.

This Mytrip deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1711:00 pmBGY - ORD
1 stop22h 00mMultiple Airlines
Sun 9/213:45 pmORD - BGY
1 stop11h 20mMultiple Airlines
Deal found 8/11$582
This Mytrip deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2510:15 amBGY - ORD
1 stop15h 45mMultiple Airlines
Thu 10/29:15 pmORD - BGY
1 stop18h 25mMultiple Airlines
Deal found 8/11$583
This Mytrip deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1711:00 pmBGY - ORD
1 stop22h 00mMultiple Airlines
Mon 9/223:45 pmORD - BGY
1 stop11h 15mMultiple Airlines
Deal found 8/12$589
This British Airways deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2511:10 amMXP - ORD
1 stop13h 13mBritish Airways
Sat 10/119:15 pmORD - MXP
1 stop19h 25mBritish Airways
Deal found 8/12$599
This United Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/169:10 amMXP - ORD
1 stop12h 45mUnited Airlines
Tue 9/237:11 amORD - MXP
2 stops27h 49mUnited Airlines
Deal found 8/12$600
This Booking.com deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/811:45 amLIN - ORD
1 stop13h 10mAer Lingus
Fri 11/143:55 pmORD - LIN
1 stop12h 10mAer Lingus
Deal found 8/12$601
This oojo deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/177:00 amLIN - ORD
1 stop13h 10mITA Airways
Sun 9/213:00 pmORD - LIN
1 stop23h 10mITA Airways
Deal found 8/12$602
This United Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1510:30 amMXP - ORD
1 stop12h 50mUnited Airlines
Sat 11/227:15 amORD - MXP
1 stop19h 40mUnited Airlines
Deal found 8/11$602
This Flighttix deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flighttix is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/293:20 pmMXP - ORD
Nonstop9h 50mLufthansa
Sun 9/149:35 pmORD - MXP
Nonstop8h 45mLufthansa
Deal found 8/12$603
This United Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1612:45 pmLIN - ORD
1 stop14h 10mUnited Airlines
Tue 9/231:12 pmORD - LIN
2 stops15h 48mUnited Airlines
Deal found 8/12$604
This Lufthansa deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Lufthansa is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/87:00 amMXP - ORD
1 stop13h 10mLufthansa
Thu 11/139:50 pmORD - MXP
1 stop11h 55mLufthansa
Deal found 8/12$604
This Mytrip deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/168:25 pmBGY - ORD
2 stops30h 30mMultiple Airlines
Tue 9/237:05 pmORD - BGY
2 stops20h 30mMultiple Airlines
Deal found 8/12$604

Cheapflights Fare Finder

 
Customize your flight search to find flights from Milan to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 13, 2025.
Use the filters below to find and compare flights from Milan to Chicago that are best for you.

Fly from

Milan

Fly to

Chicago

Route

Depart

Return

Price

BergamoChicago

BGY - ORD

BGYORD

Bergamo Orio Al Serio

Thu 9/18

10:15 am-7:00 pm

1 stop15h 45m

Chicago O'Hare Intl

Sun 9/21

3:45 pm-10:05 am

1 stop11h 20m

$582

BergamoChicago

BGY - ORD

BGYORD

Bergamo Orio Al Serio

Wed 9/17

11:00 pm-2:00 pm

1 stop22h 00m

Chicago O'Hare Intl

Sun 9/21

3:45 pm-10:05 am

1 stop11h 20m

$582

BergamoChicago

BGY - ORD

BGYORD

Bergamo Orio Al Serio

Thu 9/25

10:15 am-7:00 pm

1 stop15h 45m

Chicago O'Hare Intl

Thu 10/2

9:15 pm-10:40 pm

1 stop18h 25m

$583

BergamoChicago

BGY - ORD

BGYORD

Bergamo Orio Al Serio

Wed 9/17

11:00 pm-2:00 pm

1 stop22h 00m

Chicago O'Hare Intl

Mon 9/22

3:45 pm-10:00 am

1 stop11h 15m

$589

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Thu 9/25

11:10 am-5:23 pm

1 stop13h 13m

Chicago O'Hare Intl

Sat 10/11

9:15 pm-11:40 pm

1 stop19h 25m

$599

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Tue 9/16

9:10 am-2:55 pm

1 stop12h 45m

Chicago O'Hare Intl

Tue 9/23

7:11 am-6:00 pm

2 stops27h 49m

$600

MilanChicago

LIN - ORD

LINORD

Milan Linate

Sat 11/8

11:45 am-5:55 pm

1 stop13h 10m

Chicago O'Hare Intl

Fri 11/14

3:55 pm-11:05 am

1 stop12h 10m

$601

MilanChicago

LIN - ORD

LINORD

Milan Linate

Wed 9/17

7:00 am-1:10 pm

1 stop13h 10m

Chicago O'Hare Intl

Sun 9/21

3:00 pm-9:10 pm

1 stop23h 10m

$602

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Thu 11/6

10:40 am-11:18 am

2 stops31h 38m

Chicago O'Hare Intl

Thu 11/13

3:35 pm-9:55 am

1 stop11h 20m

$602

MilanChicago

LIN - ORD

LINORD

Milan Linate

Thu 9/18

9:00 pm-1:10 pm

1 stop23h 10m

Chicago O'Hare Intl

Sun 9/21

3:00 pm-9:10 pm

1 stop23h 10m

$602

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/10

Showing 1-10 of 60 results
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The best insider tips for Milan to Chicago flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Milan to Chicago trip
Airports
MXP

For a quick departure at MXP, consider purchasing fast track security access online, available in both terminals.

Read more about MXPby Ramsey Qubein
ORD

Expect long walks to immigration at ORD's Terminal 5. Be prepared for extensive lines upon arrival.

Read more about ORDby Ramsey Qubein
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD and MXP

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more

Best time to book a flight from Milan to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Milan with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Milan to Chicago

How far ahead should I book a flight from Milan to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Milan to Chicago. Price data was last updated on August 8, 2025.

The price you pay for your flight from Milan to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 13 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Milan to Chicago?

Currently, August is the cheapest month in which you can book a flight from Milan to Chicago (average of $245). Flying from Milan to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from MIL to CHI?

Find hourly flight availability from Milan to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 13, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 38% on flights from Milan to Chicago by exploring options for tickets in the evening.

Weekly flight availability from Milan to Chicago

Explore weekly flight availability from Milan to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated August 13, 2025.

The most flights from MIL to CHI are scheduled on a Monday (5 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (5 on average).

How much does it cost to fly round-trip from Milan to Chicago?

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated August 13, 2025.
Get a feel of what it's like to fly with United Airlines, Aer Lingus, and TAP AIR PORTUGAL from Milan to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,920 reviews

Entertainment

7.1

Crew

8.1

Food

6.6

Comfort

7.3

Overall

7.4

Boarding

7.7

Reviews

1 / 20
4.0
Okay

Thomas,Apr 2025

TPE - SFO

The boarding experience was okay. The dietary food choices were limited, the midway snacks were hard and dry. The seat was uncomfortable - stiff seat cushion, seat back kept springing back to the upright position, narrow seat width. Love the app and the ability to track my luggage. Flight crew was efficient.
United Airlines
7.4
Good
8,920 reviews
United Airlines
7.4
Good
8,920 reviews

Entertainment

7.1

Crew

8.1

Food

6.6

Comfort

7.3

Overall

7.4

Boarding

7.7

Reviews

1 / 20
4.0
Okay

Thomas,Apr 2025

TPE - SFO

The boarding experience was okay. The dietary food choices were limited, the midway snacks were hard and dry. The seat was uncomfortable - stiff seat cushion, seat back kept springing back to the upright position, narrow seat width. Love the app and the ability to track my luggage. Flight crew was efficient.
Aer Lingus
7.1
Good
1,210 reviews
United Airlines
7.4
Good
8,920 reviews

Entertainment

7.1

Crew

8.1

Food

6.6

Comfort

7.3

Overall

7.4

Boarding

7.7

Reviews

1 / 20
4.0
Okay

Thomas,Apr 2025

TPE - SFO

The boarding experience was okay. The dietary food choices were limited, the midway snacks were hard and dry. The seat was uncomfortable - stiff seat cushion, seat back kept springing back to the upright position, narrow seat width. Love the app and the ability to track my luggage. Flight crew was efficient.
TAP AIR PORTUGAL
7.1
Good
1,945 reviews
United Airlines
7.4
Good
8,920 reviews

Entertainment

7.1

Crew

8.1

Food

6.6

Comfort

7.3

Overall

7.4

Boarding

7.7

Reviews

1 / 20
4.0
Okay

Thomas,Apr 2025

TPE - SFO

The boarding experience was okay. The dietary food choices were limited, the midway snacks were hard and dry. The seat was uncomfortable - stiff seat cushion, seat back kept springing back to the upright position, narrow seat width. Love the app and the ability to track my luggage. Flight crew was efficient.
Lufthansa
6.8
Okay
7,317 reviews
United Airlines
7.4
Good
8,920 reviews

Entertainment

7.1

Crew

8.1

Food

6.6

Comfort

7.3

Overall

7.4

Boarding

7.7

Reviews

1 / 20
4.0
Okay

Thomas,Apr 2025

TPE - SFO

The boarding experience was okay. The dietary food choices were limited, the midway snacks were hard and dry. The seat was uncomfortable - stiff seat cushion, seat back kept springing back to the upright position, narrow seat width. Love the app and the ability to track my luggage. Flight crew was efficient.
British Airways
6.7
Okay
7,265 reviews
United Airlines
7.4
Good
8,920 reviews

Entertainment

7.1

Crew

8.1

Food

6.6

Comfort

7.3

Overall

7.4

Boarding

7.7

Reviews

1 / 20
4.0
Okay

Thomas,Apr 2025

TPE - SFO

The boarding experience was okay. The dietary food choices were limited, the midway snacks were hard and dry. The seat was uncomfortable - stiff seat cushion, seat back kept springing back to the upright position, narrow seat width. Love the app and the ability to track my luggage. Flight crew was efficient.

Related info for your journey

Find useful and relevant information for your journey from Milan to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines flying from Milan to Chicago round-trip?

    Currently priced at $599, British Airways will fly you from Milan to Chicago and back. In addition to British Airways, many other airlines offer competitively priced options for your trip. Check Cheapflights for deals on United Airlines for as low as $600. British Airways is currently priced 13% below the average price you’ll pay for this route.

  • What are the most popular routes from Milan to Chicago?

    The most popular flight routes from Milan to Chicago are Milan Malpensa - Chicago O'Hare Intl, Milan Linate - Chicago O'Hare Intl and Bergamo Orio Al Serio - Chicago O'Hare Intl.

  • What are the most reliable airlines from Milan to Chicago?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Milan to Chicago on time: Brussels Airlines (67%), Qatar Airways (50%), Air Canada (40%).

  • What are the cheapest flights from Milan to Chicago?

    Looking for the cheapest flight from Milan to Chicago? While on average our users pay $1,889, our data indicates the cheapest price to be $614. The most popular route (Milan Malpensa - Chicago O'Hare Intl), is priced around $449.

  • Can I find deals for flights from Milan to Chicago that include hotel bookings?

    Yes. In addition to deals on Milan to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Milan to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Milan to Chicago.

  • Can I find deals for business class flights from Milan to Chicago?

    Yes. Cheapflights offers flight deals from Milan to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Milan to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Milan to Chicago (average of $245). Flying from Milan to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Valparaiso
Chesterton

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Alternative routes for Milan to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Malpensa to O'Hare Intl flights
Linate to O'Hare Intl flights
Bergamo to O'Hare Intl flights
Malpensa to St. Louis flights
Verona to O'Hare Intl flights
Malpensa to Moline flights

Top 2 airlines flying from Milan to Chicago

Discover the top 2 airlines that operate flights from Milan to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
British AirwaysCheapest$525Average$716FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$626Average$943FlexibilityNo cancel feeOn-time69%

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