Chicago

$306+ 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 5/8. Fares are subject to change and may not be available on all flights or dates of travel.
MIL — CHI
Apr 6 — Apr 131
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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 Saturday or Monday 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 April 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$522
(lol.travel)

One-way from

$306
(Mytrip)

Popular in

July

Cheapest in

November

Average price

$622

Good round-trip deal

$824 or less

Good one-way deal

$759 or less
Provider with most accurate pricing for Milan (MIL)-Chicago (CHI) flight deals.
Provider most trusted by Cheapflights users for Milan (MIL)-Chicago (CHI) flights.
From Milan (MIL) to Chicago (CHI)
One-way flight from Milan (MIL) to Chicago (CHI)
Highest demand for flights based on searches. 18% potential increase in price ($151 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease ($17 potential savings vs. average RT price).
Average for round-trip flights in April 2025
Price to beat on a round-trip flight from Milan (MIL) to Chicago (CHI).
Price to beat on a one-way flight from Milan (MIL) to Chicago (CHI).

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 April 1, 2025.

This lol.travel deal was found by Cheapflights users on 3/31. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/109:45 pmMXP - ORD
1 stop21h 00mBritish Airways
Thu 4/248:20 pmORD - MXP
1 stop20h 20mBritish Airways
Deal found 3/31$522
This American Airlines deal was found by Cheapflights users on 3/31. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/211:10 amMXP - ORD
2 stops19h 39mAmerican Airlines
Fri 5/97:15 pmORD - MXP
1 stop20h 45mAmerican Airlines
Deal found 3/31$523
This British Airways deal was found by Cheapflights users on 3/31. 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.
Wed 5/217:25 amLIN - ORD
1 stop14h 15mBritish Airways
Tue 5/2710:25 pmORD - LIN
1 stop11h 50mBritish Airways
Deal found 3/31$525
This American Airlines deal was found by Cheapflights users on 3/31. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/611:10 amLIN - ORD
1 stop12h 50mAmerican Airlines
Wed 5/144:55 pmORD - LIN
1 stop13h 40mAmerican Airlines
Deal found 3/31$526
This American Airlines deal was found by Cheapflights users on 4/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/287:25 pmMXP - ORD
1 stop23h 20mMultiple Airlines
Mon 5/59:15 pmORD - MXP
1 stop16h 30mMultiple Airlines
Deal found 4/1$527
This oojo deal was found by Cheapflights users on 3/31. 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.
Thu 5/88:45 pmMXP - ORD
2 stops26h 25mScandinavian Airlines
Mon 5/127:15 pmORD - MXP
2 stops17h 40mScandinavian Airlines
Deal found 3/31$528
This Iberia deal was found by Cheapflights users on 3/30. 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 Iberia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/1511:10 amMXP - ORD
1 stop13h 24mIberia
Thu 5/2211:45 amORD - MXP
1 stop14h 25mIberia
Deal found 3/30$531
This Finnair deal was found by Cheapflights users on 3/31. 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 Finnair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/111:05 amMXP - ORD
1 stop13h 45mFinnair
Wed 5/79:30 pmORD - MXP
1 stop13h 45mFinnair
Deal found 3/31$546
This Iberia deal was found by Cheapflights users on 3/31. 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 Iberia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/107:25 amLIN - ORD
1 stop13h 30mMultiple Airlines
Thu 4/174:30 pmORD - LIN
1 stop20h 05mMultiple Airlines
Deal found 3/31$552
This ITA Airways deal was found by Cheapflights users on 3/31. 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 ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/157:00 amLIN - ORD
1 stop13h 10mITA Airways
Sun 9/283:00 pmORD - LIN
1 stop22h 10mITA Airways
Deal found 3/31$580
This Iberia deal was found by Cheapflights users on 3/31. 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 Iberia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/107:50 amLIN - ORD
1 stop13h 25mIberia
Sun 4/274:30 pmORD - LIN
1 stop11h 30mIberia
Deal found 3/31$582
This Travelis deal was found by Cheapflights users on 3/31. 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 Travelis is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/106:40 amLIN - ORD
1 stop14h 30mKLM
Wed 4/234:50 pmORD - LIN
1 stop16h 05mKLM
Deal found 3/31$597

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 April 1, 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

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Mon 4/28

7:25 pm-11:45 am

1 stop23h 20m

Chicago O'Hare Intl

Mon 5/5

9:15 pm-6:00 pm

1 stop13h 45m

$522

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Fri 5/2

11:10 am-11:49 pm

2 stops19h 39m

Chicago O'Hare Intl

Fri 5/9

7:15 pm-11:00 pm

1 stop20h 45m

$523

MilanChicago

LIN - ORD

LINORD

Milan Linate

Wed 5/21

7:25 am-2:40 pm

1 stop14h 15m

Chicago O'Hare Intl

Tue 5/27

10:25 pm-5:15 pm

1 stop11h 50m

$525

MilanChicago

LIN - ORD

LINORD

Milan Linate

Tue 5/6

11:10 am-5:00 pm

1 stop12h 50m

Chicago O'Hare Intl

Wed 5/14

4:55 pm-1:35 pm

1 stop13h 40m

$526

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Mon 4/28

7:25 pm-11:45 am

1 stop23h 20m

Chicago O'Hare Intl

Mon 5/5

9:15 pm-8:45 pm

1 stop16h 30m

$527

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Thu 5/8

8:45 pm-4:10 pm

2 stops26h 25m

Chicago O'Hare Intl

Mon 5/12

7:15 pm-7:55 pm

2 stops17h 40m

$528

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Thu 5/15

11:10 am-5:34 pm

1 stop13h 24m

Chicago O'Hare Intl

Thu 5/22

11:45 am-9:10 am

1 stop14h 25m

$531

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Thu 5/1

11:05 am-5:50 pm

1 stop13h 45m

Chicago O'Hare Intl

Sun 5/11

9:30 pm-6:15 pm

1 stop13h 45m

$546

MilanChicago

LIN - ORD

LINORD

Milan Linate

Thu 4/10

7:25 am-1:55 pm

1 stop13h 30m

Chicago O'Hare Intl

Thu 4/17

4:30 pm-7:35 pm

1 stop20h 05m

$552

MilanChicago

LIN - ORD

LINORD

Milan Linate

Mon 9/15

7:00 am-1:10 pm

1 stop13h 10m

Chicago O'Hare Intl

Sun 9/28

3:00 pm-8:10 pm

1 stop22h 10m

$580

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/31

Showing 1-10 of 60 results
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Compare providers for flights from Milan to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Milan to Chicago in April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*1 star
FlightHubPrice Accuracy3 starsTrust Score*3 stars
FlightnetworkPrice Accuracy-Trust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
OvagoPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Milan-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Milan-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Milan-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Milan-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Milan-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 March 28, 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 $323). 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 April 1, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 39% on flights from Milan to Chicago by exploring options for tickets in the evening.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 April 1, 2025.
Get a feel of what it's like to fly with Emirates, Delta and KLM from Milan to Chicago by reading reviews from past customers. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Overall

8.0

Crew

8.3

Entertainment

8.2

Food

7.8

Comfort

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Jun 2024

DXB - IAH

It was not a good experience the seats were small and uncomfortable the food was not good and they forgot to serve me my breakfast - there were 5 us in 2 rows that they just completely skipped us. Very disappointed.

Overall

8.0

Crew

8.3

Entertainment

8.2

Food

7.8

Comfort

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Jun 2024

DXB - IAH

It was not a good experience the seats were small and uncomfortable the food was not good and they forgot to serve me my breakfast - there were 5 us in 2 rows that they just completely skipped us. Very disappointed.
8.0
Very good

Overall

8.0

Crew

8.3

Entertainment

8.2

Food

7.8

Comfort

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Jun 2024

DXB - IAH

It was not a good experience the seats were small and uncomfortable the food was not good and they forgot to serve me my breakfast - there were 5 us in 2 rows that they just completely skipped us. Very disappointed.

Overall

8.0

Crew

8.3

Entertainment

8.2

Food

7.8

Comfort

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Jun 2024

DXB - IAH

It was not a good experience the seats were small and uncomfortable the food was not good and they forgot to serve me my breakfast - there were 5 us in 2 rows that they just completely skipped us. Very disappointed.

Overall

8.0

Crew

8.3

Entertainment

8.2

Food

7.8

Comfort

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Jun 2024

DXB - IAH

It was not a good experience the seats were small and uncomfortable the food was not good and they forgot to serve me my breakfast - there were 5 us in 2 rows that they just completely skipped us. Very disappointed.

Overall

8.0

Crew

8.3

Entertainment

8.2

Food

7.8

Comfort

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Jun 2024

DXB - IAH

It was not a good experience the seats were small and uncomfortable the food was not good and they forgot to serve me my breakfast - there were 5 us in 2 rows that they just completely skipped us. Very disappointed.

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 $522, 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. Search Cheapflights for deals from American Airlines and Scandinavian Airlines - these airlines can fly you to your destination from $523 and $528, respectively. British Airways is currently priced 20% below the average price you’ll pay for this route.

  • What are the cheapest airlines to fly from Milan to Chicago one-way?

    $358 is the cheapest one-way deal found within the past few days, from Icelandair. You may also be able to find cheap deals on TAP AIR PORTUGAL and Air Serbia, with prices starting from $402 and $446, respectively.

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

  • What are the cheapest flights from Milan to Chicago?

    Looking for the cheapest flight from Milan to Chicago? While on average our users pay $1,565, our data indicates the cheapest price to be $594. The most popular route (Milan Malpensa - Chicago O'Hare Intl), is priced around $472.

  • 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 $323). 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 Milan?

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

Browse thousands of different options on Cheapflights for your next trip

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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.

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 April 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
TAP AIR PORTUGALCheapest$537Average$564FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$625Average$864FlexibilityNo cancel feeOn-time69%
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