HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$343+ 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 6/10. Fares are subject to change and may not be available on all flights or dates of travel.
MIL — CHI
Apr 27 — May 41
Sun 4/27
Sun 5/4
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Milan to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Milan to Chicago are usually found in November or February, booked 13 days in advance, depart on a Monday or Thursday 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 22, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$548
(American Airlines)

One-way from

$343
(Mytrip)

Popular in

July

Cheapest in

November

Average price

$622

Good round-trip deal

$1,073 or less

Good one-way deal

$755 or less
Provider with most accurate pricing for Milan (MIL)-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Milan (MIL)-Chicago (CHI) flights.
Search Deals
From Milan (MIL) to Chicago (CHI)
Search Deals
One-way flight from Milan (MIL) to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 19% potential increase in price ($161 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
Search Deals
Price to beat on a round-trip flight from Milan (MIL) to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Milan (MIL) to Chicago (CHI).
Search Deals

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 22, 2025.

This Booking.com deal was found by Cheapflights users on 4/21. 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.
Mon 4/2811:10 amMXP - ORD
1 stop13h 29mBritish Airways
Mon 5/1210:25 pmORD - MXP
1 stop12h 35mBritish Airways
Deal found 4/21$543
This Iberia deal was found by Cheapflights users on 4/20. 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.
Sun 5/411:10 amMXP - ORD
1 stop13h 29mMultiple Airlines
Sun 5/117:15 pmORD - MXP
1 stop16h 15mMultiple Airlines
Deal found 4/20$544
This American Airlines deal was found by Cheapflights users on 4/21. 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.
Wed 9/177:25 amLIN - ORD
1 stop15h 30mAmerican Airlines
Sun 9/218:40 pmORD - LIN
1 stop13h 35mAmerican Airlines
Deal found 4/21$547
This American Airlines deal was found by Cheapflights users on 4/21. 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.
Wed 9/178:10 amMXP - ORD
1 stop14h 45mAmerican Airlines
Sun 9/2110:35 pmORD - MXP
1 stop14h 00mAmerican Airlines
Deal found 4/21$547
This Iberia deal was found by Cheapflights users on 4/21. 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 5/87:25 amLIN - ORD
1 stop15h 30mBritish Airways
Mon 5/127:15 pmORD - LIN
1 stop11h 20mBritish Airways
Deal found 4/21$549
This Iberia deal was found by Cheapflights users on 4/21. 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.
Fri 5/1611:10 amMXP - ORD
1 stop13h 24mIberia
Tue 5/2011:45 amORD - MXP
1 stop14h 25mIberia
Deal found 4/21$555
This Gotogate deal was found by Cheapflights users on 4/21. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/113:10 pmMXP - ORD
1 stop13h 05mIcelandair
Tue 5/2710:15 pmORD - MXP
1 stop32h 55mIcelandair
Deal found 4/21$579
This oojo deal was found by Cheapflights users on 4/21. 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 9/178:05 pmMXP - ORD
1 stop27h 05mScandinavian Airlines
Sun 9/217:15 pmORD - MXP
2 stops17h 30mScandinavian Airlines
Deal found 4/21$580
This Trip.com deal was found by Cheapflights users on 4/21. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/287:25 amLIN - ORD
1 stop16h 35mMultiple Airlines
Mon 5/1210:25 pmORD - LIN
1 stop11h 50mMultiple Airlines
Deal found 4/21$582
This Mytrip deal was found by Cheapflights users on 4/21. 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 5/2111:00 pmBGY - ORD
2 stops29h 15mMultiple Airlines
Wed 5/287:25 pmORD - BGY
2 stops21h 40mMultiple Airlines
Deal found 4/21$592
This lol.travel deal was found by Cheapflights users on 4/21. 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.
Wed 5/711:15 amMXP - ORD
2 stops15h 57mAir Canada
Sun 5/113:50 pmORD - MXP
2 stops15h 10mAir Canada
Deal found 4/21$629
This oojo deal was found by Cheapflights users on 4/20. 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.
Sun 5/187:00 amLIN - ORD
1 stop13h 10mITA Airways
Sun 5/253:00 pmORD - LIN
1 stop12h 10mITA Airways
Deal found 4/20$631

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 22, 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

Wed 5/7

11:10 am-5:34 pm

1 stop13h 24m

Chicago O'Hare Intl

Sun 5/11

7:15 pm-6:30 pm

1 stop16h 15m

$543

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Sun 5/4

11:10 am-5:39 pm

1 stop13h 29m

Chicago O'Hare Intl

Sun 5/11

7:15 pm-6:30 pm

1 stop16h 15m

$544

MilanChicago

LIN - ORD

LINORD

Milan Linate

Wed 9/17

7:25 am-3:55 pm

1 stop15h 30m

Chicago O'Hare Intl

Sun 9/21

8:40 pm-5:15 pm

1 stop13h 35m

$547

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Wed 9/17

8:10 am-3:55 pm

1 stop14h 45m

Chicago O'Hare Intl

Sun 9/21

10:35 pm-7:35 pm

1 stop14h 00m

$547

MilanChicago

LIN - ORD

LINORD

Milan Linate

Thu 5/8

7:25 am-3:55 pm

1 stop15h 30m

Chicago O'Hare Intl

Mon 5/12

7:15 pm-1:35 pm

1 stop11h 20m

$549

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Fri 5/16

11:10 am-5:34 pm

1 stop13h 24m

Chicago O'Hare Intl

Tue 5/20

11:45 am-9:10 am

1 stop14h 25m

$555

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Sun 5/11

3:10 pm-9:15 pm

1 stop13h 05m

Chicago O'Hare Intl

Tue 5/27

10:15 pm-2:10 pm

1 stop32h 55m

$579

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Wed 9/17

8:05 pm-4:10 pm

1 stop27h 05m

Chicago O'Hare Intl

Sun 9/21

7:15 pm-7:45 pm

2 stops17h 30m

$580

BergamoChicago

BGY - ORD

BGYORD

Bergamo Orio Al Serio

Wed 5/21

11:00 pm-9:15 pm

2 stops29h 15m

Chicago O'Hare Intl

Wed 5/28

7:25 pm-12:05 am

2 stops21h 40m

$592

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Wed 5/7

11:15 am-8:12 pm

2 stops15h 57m

Chicago O'Hare Intl

Sun 5/11

3:50 pm-2:00 pm

2 stops15h 10m

$629

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/21

Showing 1-10 of 60 results
1
2
3
...
6

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
FlightHubPrice Accuracy3 starsTrust Score*2 stars
AranGrantPrice Accuracy3 starsTrust Score*3 stars
FlightnetworkPrice Accuracy-Trust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
OvagoPrice Accuracy3 starsTrust Score*2 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 AranGrant to be most consistent on Cheapflights vs. AranGrant Users can find the same prices on Milan-Chicago flight deals on Cheapflights vs. AranGrant >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 AranGrant the most. AranGrant 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 April 18, 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 April 22, 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.

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 April 22, 2025.

The most flights from MIL to CHI are scheduled on a Monday (5 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (4 on average).

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 22, 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.
Emirates
8.0
Very good
3,205 reviews

Food

7.8

Overall

8.0

Boarding

8.1

Entertainment

8.2

Comfort

8.0

Crew

8.3

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.
Emirates
8.0
Very good
3,205 reviews
Emirates
8.0
Very good
3,205 reviews

Food

7.8

Overall

8.0

Boarding

8.1

Entertainment

8.2

Comfort

8.0

Crew

8.3

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.
Delta
8.0
Very good
7,920 reviews
Emirates
8.0
Very good
3,205 reviews

Food

7.8

Overall

8.0

Boarding

8.1

Entertainment

8.2

Comfort

8.0

Crew

8.3

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.
KLM
7.8
Good
1,331 reviews
Emirates
8.0
Very good
3,205 reviews

Food

7.8

Overall

8.0

Boarding

8.1

Entertainment

8.2

Comfort

8.0

Crew

8.3

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.
LOT
7.6
Good
1,065 reviews
Emirates
8.0
Very good
3,205 reviews

Food

7.8

Overall

8.0

Boarding

8.1

Entertainment

8.2

Comfort

8.0

Crew

8.3

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.
Finnair
7.6
Good
1,272 reviews
Emirates
8.0
Very good
3,205 reviews

Food

7.8

Overall

8.0

Boarding

8.1

Entertainment

8.2

Comfort

8.0

Crew

8.3

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 $548, American Airlines will fly you from Milan to Chicago and back. In addition to American Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from British Airways and Iberia - these airlines can fly you to your destination from $548 and $561, respectively. American Airlines is currently priced 18% below the average price you’ll pay for this route.

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

    $386 is the cheapest one-way deal found within the past few days, from TAP AIR PORTUGAL. You may also be able to find cheap deals on Air Serbia and Icelandair, with prices starting from $394 and $403, respectively.

  • 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 Milan Malpensa - Chicago Midway.

  • 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: Air Canada (100%), Austrian Airlines (100%), United Airlines (100%).

  • What are the cheapest flights from Milan to Chicago?

    Looking for the cheapest flight from Milan to Chicago? While on average our users pay $1,023, our data indicates the cheapest price to be $640. The most popular route (Milan Malpensa - Chicago O'Hare Intl), is priced around $476.

  • 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 Milan?

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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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
Verona to O'Hare Intl flights
Malpensa to Moline flights
Malpensa to St. Louis 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 April 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
TAP AIR PORTUGALCheapest$537Average$564FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$626Average$916FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.