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$320+ 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 4/22. Fares are subject to change and may not be available on all flights or dates of travel.
MIL — CHI
Apr 9 — Apr 161
Thu 4/9
Thu 4/16
1 adult, Economy
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Find cheap flights from Milan to Chicago with Cheapflights

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Cheapflights Tip: The best prices from Milan to Chicago are usually found in February or March, booked 75 days in advance, depart on a Saturday or Tuesday and return on a Tuesday

Cheap 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 March 10, 2026.

This Mytrip deal was found by Cheapflights users on 3/9. 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.
Thu 10/84:20 pm
MXP
-
ORD
1 stop32h 55m
Icelandair
Sun 10/187:25 pm
ORD
-
MXP
1 stop12h 45m
Icelandair
Deal found 3/9$494
This Mytrip deal was found by Cheapflights users on 3/7. 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.
Sat 9/194:20 pm
MXP
-
ORD
1 stop32h 55m
Icelandair
Sat 9/267:25 pm
ORD
-
MXP
1 stop12h 45m
Icelandair
Deal found 3/7$521
This Mytrip deal was found by Cheapflights users on 3/6. 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 9/810:55 pm
MXP
-
ORD
1 stop26h 20m
Icelandair
Fri 9/187:25 pm
ORD
-
MXP
1 stop12h 45m
Icelandair
Deal found 3/6$523
This lol.travel deal was found by Cheapflights users on 3/9. 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 5/17:00 pm
LIN
-
ORD
1 stop25h 10m
ITA Airways
Thu 5/73:00 pm
ORD
-
LIN
1 stop12h 10m
ITA Airways
Deal found 3/9$528
This Kiwi.com deal was found by Cheapflights users on 3/10. 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.
Wed 4/84:20 pm
MXP
-
ORD
1 stop32h 55m
Icelandair
Tue 4/147:25 pm
ORD
-
MXP
1 stop12h 45m
Icelandair
Deal found 3/10$540
This Icelandair deal was found by Cheapflights users on 3/9. 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 Icelandair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/224:20 pm
MXP
-
ORD
1 stop32h 55m
Icelandair
Tue 4/287:25 pm
ORD
-
MXP
1 stop12h 45m
Icelandair
Deal found 3/9$543
This Icelandair deal was found by Cheapflights users on 3/8. 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 Icelandair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/14:20 pm
MXP
-
ORD
1 stop32h 55m
Icelandair
Sat 10/247:30 pm
ORD
-
MXP
1 stop12h 40m
Icelandair
Deal found 3/8$545
This Kiwi.com deal was found by Cheapflights users on 3/9. 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.
Wed 4/294:20 pm
MXP
-
ORD
1 stop32h 55m
Icelandair
Tue 5/57:25 pm
ORD
-
MXP
1 stop12h 45m
Icelandair
Deal found 3/9$550
This Icelandair deal was found by Cheapflights users on 3/8. 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 Icelandair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/294:20 pm
MXP
-
ORD
1 stop32h 55m
Icelandair
Sat 10/247:30 pm
ORD
-
MXP
1 stop12h 40m
Icelandair
Deal found 3/8$553
This Mytrip deal was found by Cheapflights users on 3/9. 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 5/64:20 pm
MXP
-
ORD
1 stop32h 55m
Icelandair
Wed 5/1310:25 pm
ORD
-
MXP
1 stop33h 45m
Icelandair
Deal found 3/9$554
This Kiwi.com deal was found by Cheapflights users on 3/9. 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.
Sat 5/27:00 am
LIN
-
ORD
1 stop13h 10m
ITA Airways
Thu 5/73:00 pm
ORD
-
LIN
1 stop12h 10m
ITA Airways
Deal found 3/9$560
This Mytrip deal was found by Cheapflights users on 3/9. 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.
Fri 5/17:00 pm
LIN
-
ORD
1 stop25h 10m
ITA Airways
Mon 5/43:00 pm
ORD
-
LIN
1 stop12h 10m
ITA Airways
Deal found 3/9$572

Find 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 March 10, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$515
(Mytrip)

One-way from

$320
(Mytrip)

Popular in

July

Cheapest in

February

Average price

$623

Good round-trip deal

$681 or less

Good one-way deal

$711 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. 12% potential increase in price ($105 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
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

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 March 10, 2026.
Use the filters below to find and compare flights from Milan to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Wed 4/22

4:20 pm-6:15 pm

1 stop32h 55m

Chicago O'Hare Intl

Tue 4/28

7:25 pm-3:10 pm

1 stop12h 45m

$543

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Fri 5/22

10:55 pm-6:15 pm

1 stop26h 20m

Chicago O'Hare Intl

Mon 6/1

10:25 pm-9:55 pm

1 stop16h 30m

$559

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Sat 5/16

4:20 pm-6:15 pm

1 stop32h 55m

Chicago O'Hare Intl

Tue 5/26

10:25 pm-3:10 pm

1 stop33h 45m

$593

MilanChicago

LIN - ORD

LINORD

Milan Linate

Mon 4/20

6:40 am-2:30 pm

1 stop14h 50m

Chicago O'Hare Intl

Mon 4/27

10:15 am-8:50 am

2 stops15h 35m

$617

MilanChicago

LIN - ORD

LINORD

Milan Linate

Tue 5/5

6:50 am-12:55 pm

1 stop13h 05m

Chicago O'Hare Intl

Mon 5/18

2:25 pm-5:30 pm

2 stops20h 05m

$620

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Mon 4/13

11:40 am-9:25 pm

1 stop16h 45m

Chicago O'Hare Intl

Mon 4/27

5:10 pm-5:35 pm

1 stop17h 25m

$623

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Mon 4/20

11:25 am-8:40 pm

2 stops16h 15m

Chicago O'Hare Intl

Mon 4/27

3:30 pm-2:45 pm

2 stops16h 15m

$626

MilanChicago

LIN - ORD

LINORD

Milan Linate

Fri 4/24

6:40 am-2:15 pm

1 stop14h 35m

Chicago O'Hare Intl

Sun 4/26

5:10 pm-1:55 pm

1 stop13h 45m

$641

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Tue 5/5

11:25 am-8:40 pm

2 stops16h 15m

Chicago O'Hare Intl

Thu 5/14

10:24 am-12:05 pm

1 stop18h 41m

$642

MilanChicago

LIN - ORD

LINORD

Milan Linate

Thu 4/9

11:00 am-10:16 pm

2 stops18h 16m

Chicago O'Hare Intl

Wed 4/22

11:19 am-8:50 am

2 stops14h 31m

$646

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/5

Showing 1-10 of 60 resultsSorted by cheapest first
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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 March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice Accuracy2 starsTrust Score*3 stars
AranGrantPrice Accuracy2 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 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.

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 March 6, 2026.

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 75 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, November is the cheapest month in which you can book a flight from Milan to Chicago (average of $431). Flying from Milan to Chicago in January is currently the most expensive (average of $968). 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.

How often are flights from Milan to Chicago delayed?

About 22% of weekly flights between Milan and Chicago have experienced delays in the past year, with the average delay time being 209 minutes.

What is the most punctual flight time for Milan to Chicago flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Friday tends to have the lowest number of delays on this route, whereas Tuesday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Milan to Chicago flights?

Over the last year, United Airlines have had the lowest number of delays on this route, with just 21% of flights being delayed.

The best insider tips for Milan to Chicago flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Milan to Chicago trip
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD and MXP

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more

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 March 10, 2026.
Get a feel of what it's like to fly with United Airlines and Lufthansa from Milan to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,409 reviews

Comfort

7.3

Entertainment

7.1

Overall

7.4

Boarding

7.7

Crew

8.1

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
9,409 reviews
United Airlines
7.4
Good
9,409 reviews

Comfort

7.3

Entertainment

7.1

Overall

7.4

Boarding

7.7

Crew

8.1

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
Lufthansa
6.8
Okay
7,840 reviews
United Airlines
7.4
Good
9,409 reviews

Comfort

7.3

Entertainment

7.1

Overall

7.4

Boarding

7.7

Crew

8.1

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

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.

  • How long is the flight from Milan to Chicago?

    Airlines like Icelandair, Delta, and United Airlines fly from Milan to Chicago in about 13h 05m. The time it takes to get you to your destination can typically vary by up to 19h 50m. The distance from Milan to Chicago is about 4536 mi. This flight may include one or multiple stops.

  • What is the cheapest airline to fly from Milan to Chicago round-trip?

    Currently priced at $695, United Airlines will fly you from Milan to Chicago and back. In addition to United Airlines, many other airlines offer competitively priced options for your trip. United Airlines is currently priced 4% below the average price you’ll pay for this route.

  • 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 $784, our data indicates the cheapest price to be $626. The most popular route (Milan Malpensa - Chicago O'Hare Intl), is priced around $552.

  • 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, November is the cheapest month in which you can book a flight from Milan to Chicago (average of $431). Flying from Milan to Chicago in January is currently the most expensive (average of $968). 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 Chicago?

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

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 St. Louis flights

Top airline flying from Milan to Chicago

Discover the top airline 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 March 10, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$695Average$943FlexibilityNo cancel feeOn-time69%

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