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$319+ 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 1/13. Fares are subject to change and may not be available on all flights or dates of travel.
MIL — CHI
Dec 23 — Dec 301
Mon 12/23
Mon 12/30
1 adult, Economy
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The best prices from Milan to Chicago are usually found in November or February, booked 64 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 December 18, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$515
(Mytrip)

One-way from

$319
(Kissandfly.com)

Popular in

July

Cheapest in

November

Average price

$663
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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From Milan (MIL) to Chicago (CHI)
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One-way flight from Milan (MIL) to Chicago (CHI)
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High demand for flights, 19% potential price rise
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Best time to find cheap flights, 2% potential price drop
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Average for round-trip flights in December 2024
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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 December 18, 2024.

This British Airways deal was found by Cheapflights users on 12/18. 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 12/2511:20 amMXP - ORD
1 stop14h 25mBritish Airways
Tue 12/3111:45 amORD - MXP
1 stop13h 25mBritish Airways
Deal found 12/18$687
This TAP AIR PORTUGAL deal was found by Cheapflights users on 12/18. 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 TAP AIR PORTUGAL is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/256:20 amMXP - ORD
1 stop16h 10mTAP AIR PORTUGAL
Wed 1/17:15 pmORD - MXP
1 stop14h 40mTAP AIR PORTUGAL
Deal found 12/18$691
This American Airlines deal was found by Cheapflights users on 12/17. 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 12/241:10 pmMXP - ORD
1 stop32h 35mAmerican Airlines
Tue 12/3111:45 amORD - MXP
1 stop13h 25mAmerican Airlines
Deal found 12/17$708
This Expedia deal was found by Cheapflights users on 12/17. 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.
Tue 12/316:00 amMXP - ORD
2 stops16h 15mLufthansa
Tue 1/76:20 pmORD - MXP
2 stops16h 20mLufthansa
Deal found 12/17$740
This Kiwi.com deal was found by Cheapflights users on 12/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/268:00 pmMXP - ORD
1 stop26h 50mScandinavian Airlines
Thu 1/27:10 pmORD - MXP
1 stop13h 05mScandinavian Airlines
Deal found 12/18$753
This Ovago deal was found by Cheapflights users on 12/17. 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 Ovago is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/247:55 amLIN - ORD
1 stop13h 35mIberia
Tue 12/314:45 pmORD - LIN
1 stop19h 55mIberia
Deal found 12/17$772
This FlightHub deal was found by Cheapflights users on 12/18. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1910:25 amMXP - ORD
1 stop16h 35mLOT
Sun 12/299:55 pmORD - MXP
2 stops38h 10mLOT
Deal found 12/18$776
This KAYAK deal was found by Cheapflights users on 12/17. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/301:40 pmLIN - ORD
1 stop32h 35mLufthansa
Mon 1/133:55 pmORD - LIN
1 stop11h 05mLufthansa
Deal found 12/17$787
This Expedia deal was found by Cheapflights users on 12/16. 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.
Mon 12/238:45 pmMXP - ORD
1 stop25h 00mMultiple Airlines
Mon 12/306:39 pmORD - MXP
2 stops32h 06mMultiple Airlines
Deal found 12/16$795
This United Airlines deal was found by Cheapflights users on 12/18. 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.
Wed 12/259:45 amMXP - ORD
2 stops20h 40mUnited Airlines
Tue 12/3110:51 amORD - MXP
1 stop13h 39mUnited Airlines
Deal found 12/18$800
This oojo deal was found by Cheapflights users on 12/17. 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.
Fri 12/2011:10 amMXP - ORD
1 stop30h 00mTurkish Airlines
Tue 1/78:30 pmORD - MXP
1 stop37h 05mTurkish Airlines
Deal found 12/17$805
This SWISS deal was found by Cheapflights users on 12/17. 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 SWISS is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/307:00 pmMXP - ORD
2 stops26h 05mSWISS
Mon 1/139:10 pmORD - MXP
2 stops34h 05mSWISS
Deal found 12/17$861

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 2,558,603 searches. Data last updated December 18, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

BergamoChicago

BGY - ORD

BGYORD

Bergamo Orio Al Serio

Thu 2/6

7:55 am-7:55 pm

2 stops19h 00m

Chicago O'Hare Intl

Wed 2/19

3:35 pm-10:45 pm

2 stops24h 10m

$515

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Sat 4/19

8:20 pm-4:10 pm

1 stop26h 50m

Chicago O'Hare Intl

Sat 4/26

6:00 pm-12:35 am

1 stop23h 35m

$518

MilanChicago

LIN - ORD

LINORD

Milan Linate

Thu 2/6

11:45 am-7:15 pm

1 stop14h 30m

Chicago O'Hare Intl

Wed 2/19

9:00 pm-11:05 am

1 stop31h 05m

$521

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Thu 2/6

11:20 am-5:50 pm

1 stop13h 30m

Chicago O'Hare Intl

Wed 2/19

10:05 am-10:30 am

2 stops17h 25m

$523

MilanChicago

LIN - ORD

LINORD

Milan Linate

Tue 5/6

9:55 pm-1:10 pm

2 stops22h 15m

Chicago O'Hare Intl

Wed 5/14

3:00 pm-2:00 pm

2 stops16h 00m

$553

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Thu 1/16

9:55 pm-3:30 pm

2 stops24h 35m

Chicago O'Hare Intl

Wed 1/29

7:15 pm-9:05 pm

2 stops18h 50m

$560

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Thu 2/6

10:15 am-5:38 pm

1 stop14h 23m

Chicago O'Hare Intl

Wed 2/19

6:26 pm-2:40 pm

1 stop13h 14m

$563

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Thu 4/10

7:45 pm-7:40 pm

2 stops30h 55m

Chicago O'Hare Intl

Thu 4/24

9:40 pm-9:45 am

2 stops29h 05m

$574

MilanChicago

LIN - ORD

LINORD

Milan Linate

Wed 4/23

8:00 am-7:45 pm

2 stops18h 45m

Chicago O'Hare Intl

Sun 5/4

11:45 am-10:10 am

2 stops15h 25m

$593

MilanChicago

LIN - ORD

LINORD

Milan Linate

Thu 2/6

7:15 am-1:55 pm

1 stop13h 40m

Chicago O'Hare Intl

Wed 2/19

5:00 pm-1:20 pm

1 stop13h 20m

$596

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

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 December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightnetworkPrice Accuracy-Trust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*1 star
OvagoPrice Accuracy1 starTrust 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.

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 December 13, 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 64 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 December 18, 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 December 18, 2024.
Get a feel of what it's like to fly with Aer Lingus, Scandinavian Airlines and LOT 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
3,412 reviews

Boarding

8.1

Comfort

8.0

Entertainment

8.2

Crew

8.3

Overall

8.1

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
3,412 reviews
Emirates
8.1
Very good
3,412 reviews

Boarding

8.1

Comfort

8.0

Entertainment

8.2

Crew

8.3

Overall

8.1

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
8,604 reviews
Emirates
8.1
Very good
3,412 reviews

Boarding

8.1

Comfort

8.0

Entertainment

8.2

Crew

8.3

Overall

8.1

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
1,349 reviews
Emirates
8.1
Very good
3,412 reviews

Boarding

8.1

Comfort

8.0

Entertainment

8.2

Crew

8.3

Overall

8.1

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
1,133 reviews
Emirates
8.1
Very good
3,412 reviews

Boarding

8.1

Comfort

8.0

Entertainment

8.2

Crew

8.3

Overall

8.1

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.

Austrian Airlines
7.6
Good
787 reviews
Emirates
8.1
Very good
3,412 reviews

Boarding

8.1

Comfort

8.0

Entertainment

8.2

Crew

8.3

Overall

8.1

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 $518, 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 Aer Lingus and Scandinavian Airlines - these airlines can fly you to your destination from $521 and $523, respectively. TAP AIR PORTUGAL 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?

    $385 is the cheapest one-way deal found within the past few days, from Air Serbia. You may also be able to find cheap deals on Icelandair and Turkish Airlines, with prices starting from $431 and $478, 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 (89%), United Airlines (89%), SWISS (89%).

  • What are the cheapest flights from Milan to Chicago?

    Looking for the cheapest flight from Milan to Chicago? While on average our users pay $948, our data indicates the cheapest price to be $603. The most popular route (Milan Malpensa - Chicago O'Hare Intl), is priced around $382.

  • 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

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.
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 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 2,558,603 searches. Data last updated December 18, 2024.
AirlineCheapestAverageFlexibilityOn-time
Scandinavian AirlinesCheapest$350Average$420FlexibilityNo cancel feeOn-time77%
TAP AIR PORTUGALCheapest$560Average$564FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$624Average$870FlexibilityNo cancel feeOn-time69%
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