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$369+ 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 2/16. Fares are subject to change and may not be available on all flights or dates of travel.
MIL — CHI
Nov 25 — Dec 21
Mon 11/25
Mon 12/2
1 adult, Economy
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The best prices from Milan to Chicago are usually found in November or February, booked 57 days in advance, depart on a Friday or Tuesday 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 November 20, 2024.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Popular in

July

Cheapest in

November

Round-trip from

$509
(Gotogate)

One-way from

$369
(StudentUniverse)
Provider with most accurate pricing for Milan (MIL)-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Milan (MIL)-Chicago (CHI) flights.
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High demand for flights, 23% potential price rise
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Best time to find cheap flights, 31% potential price drop
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From Milan (MIL) to Chicago (CHI)
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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 November 20, 2024.

This lol.travel deal was found by Cheapflights users on 11/19. 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.
Fri 11/226:20 amMXP - ORD
1 stop16h 10mTAP AIR PORTUGAL
Fri 12/68:20 pmORD - MXP
1 stop13h 35mTAP AIR PORTUGAL
Deal found 11/19$507
This oojo deal was found by Cheapflights users on 11/19. 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.
Tue 11/2611:45 amLIN - ORD
1 stop13h 10mAer Lingus
Tue 12/33:55 pmORD - LIN
1 stop12h 10mAer Lingus
Deal found 11/19$528
This lol.travel deal was found by Cheapflights users on 11/19. 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.
Fri 12/66:55 pmLIN - ORD
1 stop26h 00mBritish Airways
Sun 12/89:45 pmORD - LIN
1 stop13h 05mBritish Airways
Deal found 11/19$554
This American Airlines deal was found by Cheapflights users on 11/19. 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.
Thu 12/510:15 amMXP - ORD
1 stop28h 31mAmerican Airlines
Mon 12/99:45 pmORD - MXP
1 stop15h 05mAmerican Airlines
Deal found 11/19$555
This Priceline deal was found by Cheapflights users on 11/19. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/411:20 amMXP - ORD
1 stop12h 40mBritish Airways
Sun 12/86:30 pmORD - MXP
1 stop12h 55mBritish Airways
Deal found 11/19$556
This Mytrip deal was found by Cheapflights users on 11/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/310:40 amMXP - ORD
2 stops34h 25mMultiple Airlines
Tue 12/103:35 pmORD - MXP
2 stops17h 55mMultiple Airlines
Deal found 11/20$566
This American Airlines deal was found by Cheapflights users on 11/19. 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 12/257:35 amLIN - ORD
1 stop13h 20mAmerican Airlines
Sat 1/259:45 pmORD - LIN
1 stop16h 50mAmerican Airlines
Deal found 11/19$591
This lol.travel deal was found by Cheapflights users on 11/19. 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.
Fri 12/612:20 pmMXP - ORD
1 stop14h 35mAir Canada
Sun 12/84:00 pmORD - MXP
2 stops13h 35mAir Canada
Deal found 11/19$593
This United Airlines deal was found by Cheapflights users on 11/19. 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.
Fri 12/66:25 amLIN - ORD
2 stops15h 20mUnited Airlines
Sun 12/81:19 pmORD - LIN
2 stops20h 36mUnited Airlines
Deal found 11/19$601
This Gotogate deal was found by Cheapflights users on 11/20. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2511:20 amLIN - ORD
1 stop14h 25mMultiple Airlines
Sat 1/255:00 pmORD - LIN
1 stop12h 15mMultiple Airlines
Deal found 11/20$611
This United Airlines deal was found by Cheapflights users on 11/19. 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 12/33:05 pmMXP - ORD
Nonstop10h 05mUnited Airlines
Tue 3/45:58 pmORD - MXP
1 stop33h 22mUnited Airlines
Deal found 11/19$612
This Expedia deal was found by Cheapflights users on 11/19. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/56:55 amLIN - ORD
1 stop12h 20mBrussels Airlines
Mon 12/95:50 pmORD - LIN
2 stops17h 00mBrussels Airlines
Deal found 11/19$627

Find flights from Milan to Chicago within your budget

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 2,629,791 searches. Data last updated November 20, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Fri 4/4

9:15 am-4:10 pm

1 stop13h 55m

Chicago O'Hare Intl

Tue 4/29

7:15 pm-7:15 pm

1 stop17h 00m

$510

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Wed 4/2

5:55 am-4:10 pm

1 stop17h 15m

Chicago O'Hare Intl

Sun 4/27

6:00 pm-12:35 am

1 stop23h 35m

$516

MilanChicago

LIN - ORD

LINORD

Milan Linate

Wed 12/4

11:45 am-5:55 pm

1 stop13h 10m

Chicago O'Hare Intl

Sun 12/8

3:55 pm-11:05 am

1 stop12h 10m

$528

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Mon 3/24

8:45 pm-7:45 pm

1 stop29h 00m

Chicago O'Hare Intl

Sat 4/5

9:15 pm-7:55 pm

1 stop15h 40m

$546

MilanChicago

LIN - ORD

LINORD

Milan Linate

Fri 12/6

6:55 pm-1:55 pm

1 stop26h 00m

Chicago O'Hare Intl

Sun 12/8

9:45 pm-5:50 pm

1 stop13h 05m

$554

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Thu 12/5

10:15 am-7:46 am

1 stop28h 31m

Chicago O'Hare Intl

Mon 12/9

9:45 pm-7:50 pm

1 stop15h 05m

$555

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Wed 12/4

11:20 am-5:00 pm

1 stop12h 40m

Chicago O'Hare Intl

Sun 12/8

6:30 pm-2:25 pm

1 stop12h 55m

$556

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Mon 3/31

10:15 pm-7:05 pm

1 stop27h 50m

Chicago O'Hare Intl

Thu 5/1

8:55 pm-9:35 pm

1 stop17h 40m

$562

MilanChicago

LIN - ORD

LINORD

Milan Linate

Thu 5/8

4:00 pm-1:10 pm

1 stop28h 10m

Chicago O'Hare Intl

Mon 5/12

3:00 pm-3:00 pm

2 stops17h 00m

$567

MilanChicago

LIN - ORD

LINORD

Milan Linate

Fri 1/10

6:55 pm-2:45 pm

1 stop26h 50m

Chicago O'Hare Intl

Fri 1/17

9:45 pm-9:35 pm

1 stop16h 50m

$571

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/18

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 November.
ProviderPrice AccuracyTrust Score*
AranGrantPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy1 starTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightnetworkPrice Accuracy-Trust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*1 star
FlightHubPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice Accuracy2 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 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.

Travel insights for flights from Milan to Chicago

Get recent, data-driven insights about flights from Milan to Chicago including ideal travel times, pricing trends, and more.

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 November 15, 2024.

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 57 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, September is the cheapest month in which you can book a flight from Milan to Chicago (average of $232). Flying from Milan to Chicago in June is currently the most expensive (average of $308). 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 November 20, 2024.

Unlike at noon, when flights are generally more expensive, you can save up to 30% 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 November 20, 2024.
Get a feel of what it's like to fly with Aer Lingus, American Airlines and Brussels Airlines 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
8.1
Very good
3,486 reviews

Overall

8.1

Crew

8.3

Comfort

8.0

Boarding

8.1

Entertainment

8.2

Food

7.9

Reviews

1 / 10

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
8.1
Very good
3,486 reviews
Emirates
8.1
Very good
3,486 reviews

Overall

8.1

Crew

8.3

Comfort

8.0

Boarding

8.1

Entertainment

8.2

Food

7.9

Reviews

1 / 10

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
8,756 reviews
Emirates
8.1
Very good
3,486 reviews

Overall

8.1

Crew

8.3

Comfort

8.0

Boarding

8.1

Entertainment

8.2

Food

7.9

Reviews

1 / 10

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
1,350 reviews
Emirates
8.1
Very good
3,486 reviews

Overall

8.1

Crew

8.3

Comfort

8.0

Boarding

8.1

Entertainment

8.2

Food

7.9

Reviews

1 / 10

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
7.7
Good
1,300 reviews
Emirates
8.1
Very good
3,486 reviews

Overall

8.1

Crew

8.3

Comfort

8.0

Boarding

8.1

Entertainment

8.2

Food

7.9

Reviews

1 / 10

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
1,165 reviews
Emirates
8.1
Very good
3,486 reviews

Overall

8.1

Crew

8.3

Comfort

8.0

Boarding

8.1

Entertainment

8.2

Food

7.9

Reviews

1 / 10

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 $509, TAP AIR PORTUGAL will fly you from Milan to Chicago and back. In addition to TAP AIR PORTUGAL, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Scandinavian Airlines and Aer Lingus - these airlines can fly you to your destination from $510 and $528, respectively. TAP AIR PORTUGAL is currently priced 19% below the average price you’ll pay for this route.

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

    $369 is the cheapest one-way deal found within the past few days, from Icelandair. You may also be able to find cheap deals on Air Serbia and TAP AIR PORTUGAL, with prices starting from $387 and $408, 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 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: Austrian Airlines (93%), United Airlines (93%), SWISS (93%).

  • What are the cheapest flights from Milan to Chicago?

    Looking for the cheapest flight from Milan to Chicago? While on average our users pay $1,111, our data indicates the cheapest price to be $493. The most popular route (Milan Malpensa - Chicago O'Hare Intl), is priced around $426.

  • 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, September is the cheapest month in which you can book a flight from Milan to Chicago (average of $232). Flying from Milan to Chicago in June is currently the most expensive (average of $308). 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

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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 3 airlines flying from Milan to Chicago

Discover the top 3 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 2,629,791 searches. Data last updated November 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
Scandinavian AirlinesCheapest$350Average$468FlexibilityNo cancel feeOn-time77%
TAP AIR PORTUGALCheapest$560Average$564FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$624Average$870FlexibilityNo cancel feeOn-time69%
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