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$345+ 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 5/10. Fares are subject to change and may not be available on all flights or dates of travel.
MIL — CHI
Feb 27 — Mar 61
Thu 2/27
Thu 3/6
1 adult, Economy
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The best prices from Milan to Chicago are usually found in November or March, booked 29 days in advance, depart on a Thursday or Wednesday 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 February 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$520
(Mytrip)

One-way from

$345
(Kiwi.com)

Popular in

July

Cheapest in

November

Average price

$562

Good round-trip deal

$796 or less

Good one-way deal

$672 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 ($153 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 February 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 February 22, 2025.

This Mytrip deal was found by Cheapflights users on 2/21. 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.
Mon 4/73:30 pmBGY - ORD
2 stops28h 50mMultiple Airlines
Mon 4/142:20 pmORD - BGY
2 stops22h 30mMultiple Airlines
Deal found 2/21$520
This Gotogate deal was found by Cheapflights users on 2/21. 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.
Fri 9/129:00 pmLIN - ORD
1 stop23h 10mITA Airways
Sat 9/203:00 pmORD - LIN
1 stop11h 40mITA Airways
Deal found 2/21$523
This Booking.com deal was found by Cheapflights users on 2/22. 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.
Sun 4/133:30 pmMXP - ORD
1 stop33h 50mIcelandair
Fri 4/1810:15 pmORD - MXP
1 stop33h 15mIcelandair
Deal found 2/22$524
This Gotogate deal was found by Cheapflights users on 2/22. 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.
Mon 3/311:20 amMXP - ORD
1 stop13h 30mScandinavian Airlines
Mon 3/178:40 pmORD - MXP
1 stop16h 30mScandinavian Airlines
Deal found 2/22$527
This Booking.com deal was found by Cheapflights users on 2/21. 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.
Tue 5/611:20 amLIN - ORD
1 stop14h 40mAer Lingus
Wed 5/143:45 pmORD - LIN
1 stop11h 55mAer Lingus
Deal found 2/21$530
This Kiwi.com deal was found by Cheapflights users on 2/20. 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.
Fri 4/1110:15 pmMXP - ORD
1 stop22h 45mAer Lingus
Sun 4/273:45 pmORD - MXP
1 stop22h 50mAer Lingus
Deal found 2/20$551
This Gotogate deal was found by Cheapflights users on 2/21. 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.
Thu 9/115:55 amMXP - ORD
1 stop17h 15mTAP AIR PORTUGAL
Thu 9/256:00 pmORD - MXP
1 stop34h 00mTAP AIR PORTUGAL
Deal found 2/21$568
This Flysmarter deal was found by Cheapflights users on 2/21. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/711:10 amMXP - ORD
1 stop13h 29mBritish Airways
Mon 4/148:20 pmORD - MXP
1 stop14h 40mBritish Airways
Deal found 2/21$573
This Mytrip deal was found by Cheapflights users on 2/21. 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.
Mon 4/73:55 pmMXP - ORD
3 stops27h 15mMultiple Airlines
Mon 4/142:20 pmORD - MXP
2 stops18h 20mMultiple Airlines
Deal found 2/21$575
This Finnair deal was found by Cheapflights users on 2/21. 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 Finnair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/711:05 amMXP - ORD
1 stop13h 45mFinnair
Tue 5/139:30 pmORD - MXP
1 stop13h 45mFinnair
Deal found 2/21$590
This Booking.com deal was found by Cheapflights users on 2/21. 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.
Thu 4/37:25 amLIN - ORD
1 stop14h 20mBritish Airways
Wed 4/97:15 pmORD - LIN
1 stop11h 20mBritish Airways
Deal found 2/21$593
This American Airlines deal was found by Cheapflights users on 2/21. 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.
Mon 4/287:25 amLIN - ORD
1 stop13h 25mAmerican Airlines
Tue 6/39:15 pmORD - LIN
1 stop14h 20mAmerican Airlines
Deal found 2/21$600

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 February 22, 2025.

Fly from

Milan

Fly to

Chicago

Route

Depart

Return

Price

BergamoChicago

BGY - ORD

BGYORD

Bergamo Orio Al Serio

Mon 4/7

3:30 pm-1:20 pm

2 stops28h 50m

Chicago O'Hare Intl

Mon 4/14

2:20 pm-7:50 pm

2 stops22h 30m

$520

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Sun 4/13

3:30 pm-6:20 pm

1 stop33h 50m

Chicago O'Hare Intl

Fri 4/18

10:15 pm-2:30 pm

1 stop33h 15m

$524

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Mon 3/3

11:20 am-5:50 pm

1 stop13h 30m

Chicago O'Hare Intl

Mon 3/17

8:40 pm-7:10 pm

1 stop16h 30m

$527

MilanChicago

LIN - ORD

LINORD

Milan Linate

Tue 5/6

11:20 am-7:00 pm

1 stop14h 40m

Chicago O'Hare Intl

Wed 5/14

3:45 pm-10:40 am

1 stop11h 55m

$530

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Fri 4/11

10:15 pm-2:00 pm

1 stop22h 45m

Chicago O'Hare Intl

Sun 4/27

3:45 pm-9:35 pm

1 stop22h 50m

$551

MilanChicago

LIN - ORD

LINORD

Milan Linate

Mon 4/7

9:00 pm-5:32 pm

2 stops27h 32m

Chicago O'Hare Intl

Mon 4/14

10:35 am-11:40 am

2 stops18h 05m

$563

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Thu 4/24

8:20 pm-4:10 pm

1 stop26h 50m

Chicago O'Hare Intl

Sun 5/4

6:00 pm-4:25 pm

1 stop15h 25m

$571

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Mon 4/7

11:10 am-5:39 pm

1 stop13h 29m

Chicago O'Hare Intl

Mon 4/14

8:20 pm-6:00 pm

1 stop14h 40m

$573

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Mon 4/7

3:55 pm-12:10 pm

3 stops27h 15m

Chicago O'Hare Intl

Mon 4/14

2:20 pm-3:40 pm

2 stops18h 20m

$575

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Wed 5/7

11:05 am-5:50 pm

1 stop13h 45m

Chicago O'Hare Intl

Tue 5/13

9:30 pm-6:15 pm

1 stop13h 45m

$590

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 60 results
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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 February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*1 star
FlightnetworkPrice Accuracy-Trust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust 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.

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 February 14, 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 29 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 February 22, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 38% 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 February 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
8.1
Very good
3,278 reviews

Entertainment

8.2

Crew

8.3

Boarding

8.1

Overall

8.1

Comfort

8.0

Food

7.9

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
8.1
Very good
3,278 reviews
Emirates
8.1
Very good
3,278 reviews

Entertainment

8.2

Crew

8.3

Boarding

8.1

Overall

8.1

Comfort

8.0

Food

7.9

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
8,203 reviews
Emirates
8.1
Very good
3,278 reviews

Entertainment

8.2

Crew

8.3

Boarding

8.1

Overall

8.1

Comfort

8.0

Food

7.9

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
1,330 reviews
Emirates
8.1
Very good
3,278 reviews

Entertainment

8.2

Crew

8.3

Boarding

8.1

Overall

8.1

Comfort

8.0

Food

7.9

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
1,079 reviews
Emirates
8.1
Very good
3,278 reviews

Entertainment

8.2

Crew

8.3

Boarding

8.1

Overall

8.1

Comfort

8.0

Food

7.9

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
1,271 reviews
Emirates
8.1
Very good
3,278 reviews

Entertainment

8.2

Crew

8.3

Boarding

8.1

Overall

8.1

Comfort

8.0

Food

7.9

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 $530, Aer Lingus will fly you from Milan to Chicago and back. In addition to Aer Lingus, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Scandinavian Airlines and Icelandair - these airlines can fly you to your destination from $534 and $556, respectively. Aer Lingus 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?

    $382 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 WestJet, with prices starting from $428 and $465, 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 cheapest flights from Milan to Chicago?

    Looking for the cheapest flight from Milan to Chicago? While on average our users pay $835, our data indicates the cheapest price to be $611. The most popular route (Milan Malpensa - Chicago O'Hare Intl), is priced around $512.

  • 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
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
Linate to O'Hare Intl flights
Bergamo to O'Hare Intl flights
Verona to O'Hare Intl flights
Malpensa to St. Louis 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 February 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
Scandinavian AirlinesCheapest$350Average$472FlexibilityNo cancel feeOn-time77%
TAP AIR PORTUGALCheapest$560Average$564FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$625Average$870FlexibilityNo cancel feeOn-time69%
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