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$303+ 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 3/3. Fares are subject to change and may not be available on all flights or dates of travel.
MIL — CHI
janv. 26 — févr. 21
dim. 1/26
dim. 2/2
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 janvier 21, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$465
(oojo)

One-way from

$303
(Kiwi.com)

Popular in

July

Cheapest in

November

Average price

$640

Good round-trip deal

$782 or less

Good one-way deal

$702 or less
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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Highest demand for flights based on searches. 19% potential increase in price ($154 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in January 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 janvier 21, 2025.

This TAP AIR PORTUGAL deal was found by Cheapflights users on 1/21. 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 TAP AIR PORTUGAL is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 4/248:20 pmMXP - ORD
1 stop26h 40mTAP AIR PORTUGAL
dim. 5/46:00 pmORD - MXP
1 stop23h 45mTAP AIR PORTUGAL
Deal found 1/21$455
This Kiwi.com deal was found by Cheapflights users on 1/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 2/197:45 pmMXP - ORD
1 stop31h 15mLOT
mer. 2/269:55 pmORD - MXP
1 stop28h 50mLOT
Deal found 1/20$470
This Mytrip deal was found by Cheapflights users on 1/21. 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.
jeu. 3/63:25 pmMXP - ORD
2 stops30h 05mMultiple Airlines
lun. 3/106:20 pmORD - MXP
2 stops18h 15mMultiple Airlines
Deal found 1/21$481
This oojo deal was found by Cheapflights users on 1/21. 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.
mar. 6/35:00 pmLIN - ORD
1 stop27h 10mITA Airways
mer. 6/253:00 pmORD - LIN
1 stop17h 10mITA Airways
Deal found 1/21$482
This Mytrip deal was found by Cheapflights users on 1/21. 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.
sam. 3/18:00 pmMXP - ORD
1 stop28h 50mScandinavian Airlines
lun. 3/317:15 pmORD - MXP
1 stop17h 00mScandinavian Airlines
Deal found 1/21$487
This Mytrip deal was found by Cheapflights users on 1/21. 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.
ven. 1/3111:10 pmBGY - ORD
2 stops22h 55mMultiple Airlines
lun. 2/34:25 pmORD - BGY
2 stops23h 30mMultiple Airlines
Deal found 1/21$488
This lol.travel deal was found by Cheapflights users on 1/20. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 3/1011:45 amLIN - ORD
1 stop33h 15mAer Lingus
mar. 3/254:55 pmORD - LIN
1 stop12h 10mAer Lingus
Deal found 1/20$501
This Fly & Visit Rome deal was found by Cheapflights users on 1/20. 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 Fly & Visit Rome is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 3/106:45 amMXP - ORD
1 stop16h 30mSWISS
mer. 3/268:05 pmORD - MXP
1 stop16h 15mSWISS
Deal found 1/20$544
This Booking.com deal was found by Cheapflights users on 1/20. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 2/286:30 amLIN - ORD
1 stop15h 00mMultiple Airlines
dim. 3/166:20 pmORD - LIN
1 stop22h 40mMultiple Airlines
Deal found 1/20$546
This Delta deal was found by Cheapflights users on 1/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 2/216:30 amLIN - ORD
1 stop15h 00mDelta
mer. 2/264:58 pmORD - LIN
2 stops14h 02mDelta
Deal found 1/20$548
This Booking.com deal was found by Cheapflights users on 1/20. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 2/69:40 pmLIN - ORD
1 stop23h 50mKLM
mer. 2/124:25 pmORD - LIN
1 stop23h 30mKLM
Deal found 1/20$550
This United Airlines deal was found by Cheapflights users on 1/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 3/266:25 amLIN - ORD
2 stops34h 29mUnited Airlines
sam. 4/55:59 pmORD - LIN
2 stops16h 36mUnited Airlines
Deal found 1/20$551

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 janvier 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

dim. 2/16

6:20 am-3:30 pm

1 stop16h 10m

Chicago O'Hare Intl

dim. 2/23

8:25 pm-11:35 pm

1 stop20h 10m

$465

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

mer. 2/19

7:45 pm-8:00 pm

1 stop31h 15m

Chicago O'Hare Intl

mer. 2/26

9:55 pm-9:45 am

1 stop28h 50m

$470

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

jeu. 3/6

11:20 am-5:50 pm

1 stop13h 30m

Chicago O'Hare Intl

lun. 3/10

8:40 pm-7:10 pm

1 stop16h 30m

$477

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

jeu. 3/6

3:25 pm-2:30 pm

2 stops30h 05m

Chicago O'Hare Intl

lun. 3/10

6:20 pm-6:35 pm

2 stops18h 15m

$481

BergamoChicago

BGY - ORD

BGYORD

Bergamo Orio Al Serio

ven. 1/31

11:10 pm-3:05 pm

2 stops22h 55m

Chicago O'Hare Intl

lun. 2/3

4:25 pm-10:55 pm

2 stops23h 30m

$488

MilanChicago

LIN - ORD

LINORD

Milan Linate

lun. 3/10

11:45 am-3:00 pm

1 stop33h 15m

Chicago O'Hare Intl

mar. 3/25

4:55 pm-11:05 am

1 stop12h 10m

$501

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

lun. 3/10

6:45 am-5:15 pm

1 stop16h 30m

Chicago O'Hare Intl

mer. 3/26

8:05 pm-6:20 pm

1 stop16h 15m

$544

MilanChicago

LIN - ORD

LINORD

Milan Linate

ven. 2/28

6:30 am-2:30 pm

1 stop15h 00m

Chicago O'Hare Intl

dim. 3/16

6:20 pm-11:00 pm

1 stop22h 40m

$546

MilanChicago

LIN - ORD

LINORD

Milan Linate

ven. 2/21

6:30 am-2:30 pm

1 stop15h 00m

Chicago O'Hare Intl

mer. 2/26

4:58 pm-2:00 pm

2 stops14h 02m

$548

MilanChicago

LIN - ORD

LINORD

Milan Linate

jeu. 2/6

9:40 pm-2:30 pm

1 stop23h 50m

Chicago O'Hare Intl

mer. 2/12

4:25 pm-10:55 pm

1 stop23h 30m

$550

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*3 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 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 January 17, 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 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, 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 $320). 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 janvier 21, 2025.

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 janvier 21, 2025.
Get a feel of what it's like to fly with Emirates, Finnair and Turkish 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
3,360 reviews

Food

7.9

Boarding

8.1

Overall

8.1

Crew

8.3

Entertainment

8.2

Comfort

8.0

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
3,360 reviews
Emirates
8.1
Very good
3,360 reviews

Food

7.9

Boarding

8.1

Overall

8.1

Crew

8.3

Entertainment

8.2

Comfort

8.0

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
8,521 reviews
Emirates
8.1
Very good
3,360 reviews

Food

7.9

Boarding

8.1

Overall

8.1

Crew

8.3

Entertainment

8.2

Comfort

8.0

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
1,341 reviews
Emirates
8.1
Very good
3,360 reviews

Food

7.9

Boarding

8.1

Overall

8.1

Crew

8.3

Entertainment

8.2

Comfort

8.0

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
1,117 reviews
Emirates
8.1
Very good
3,360 reviews

Food

7.9

Boarding

8.1

Overall

8.1

Crew

8.3

Entertainment

8.2

Comfort

8.0

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
7.6
Good
1,286 reviews
Emirates
8.1
Very good
3,360 reviews

Food

7.9

Boarding

8.1

Overall

8.1

Crew

8.3

Entertainment

8.2

Comfort

8.0

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 $465, 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 LOT and Scandinavian Airlines - these airlines can fly you to your destination from $470 and $477, respectively. TAP AIR PORTUGAL is currently priced 27% below the average price you’ll pay for this route.

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

    $362 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 TAP AIR PORTUGAL, with prices starting from $411 and $414, 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 Malpensa - Chicago Midway and Milan Linate - 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: Austrian Airlines (94%), United Airlines (94%), SWISS (94%).

  • What are the cheapest flights from Milan to Chicago?

    Looking for the cheapest flight from Milan to Chicago? While on average our users pay $1,424, our data indicates the cheapest price to be $696. The most popular route (Milan Malpensa - Chicago O'Hare Intl), is priced around $431.

  • 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 $320). 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

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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
Bergamo to O'Hare Intl flights
Linate 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 2,558,603 searches. Data last updated janvier 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
Scandinavian AirlinesCheapest$350Average$468FlexibilityNo cancel feeOn-time77%
TAP AIR PORTUGALCheapest$560Average$564FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$624Average$884FlexibilityNo cancel feeOn-time69%
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