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$362+ 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 9/18. Fares are subject to change and may not be available on all flights or dates of travel.
MIL — CHI
Aug 29 — Sep 51
Sat 8/29
Sat 9/5
1 adult, Economy
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Cheapflights Tip: The best prices from Milan to Chicago are usually found in February or November, booked 39 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 July 30, 2026.

This Icelandair deal was found by Cheapflights users on 7/29. 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.
Sun 8/234:20 pm
MXP
-
ORD
1 stop12h 05m
Icelandair
Mon 8/3110:25 pm
ORD
-
MXP
1 stop16h 30m
Icelandair
Deal found 7/29$668
This lol.travel deal was found by Cheapflights users on 7/28. 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.
Sat 8/299:20 am
MXP
-
ORD
1 stop13h 50m
Scandinavian Airlines
Mon 9/147:15 pm
ORD
-
MXP
1 stop16h 55m
Scandinavian Airlines
Deal found 7/28$670
This lol.travel deal was found by Cheapflights users on 7/29. 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.
Thu 9/249:20 am
MXP
-
ORD
1 stop13h 50m
Scandinavian Airlines
Sat 10/37:15 pm
ORD
-
MXP
2 stops15h 45m
Scandinavian Airlines
Deal found 7/29$673
This Scandinavian Airlines deal was found by Cheapflights users on 7/28. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/28:00 pm
MXP
-
ORD
1 stop27h 10m
Scandinavian Airlines
Sun 9/67:15 pm
ORD
-
MXP
1 stop16h 55m
Scandinavian Airlines
Deal found 7/28$675
This Scandinavian Airlines deal was found by Cheapflights users on 7/28. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2711:20 am
MXP
-
ORD
1 stop12h 25m
Scandinavian Airlines
Tue 11/107:15 pm
ORD
-
MXP
1 stop30h 35m
Scandinavian Airlines
Deal found 7/28$676
This ITA Airways deal was found by Cheapflights users on 7/26. 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 ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/227:05 pm
LIN
-
ORD
1 stop25h 05m
ITA Airways
Sun 9/203:00 pm
ORD
-
LIN
1 stop12h 10m
ITA Airways
Deal found 7/26$677
This Gotogate deal was found by Cheapflights users on 7/25. 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 8/269:20 am
MXP
-
ORD
1 stop13h 50m
Scandinavian Airlines
Wed 9/167:15 pm
ORD
-
MXP
1 stop16h 55m
Scandinavian Airlines
Deal found 7/25$677
This Mytrip deal was found by Cheapflights users on 7/26. 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 9/18:40 pm
BGY
-
ORD
2 stops26h 30m
Multiple Airlines
Sun 9/137:15 pm
ORD
-
BGY
2 stops17h 50m
Multiple Airlines
Deal found 7/26$677
This oojo deal was found by Cheapflights users on 7/27. 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 11/138:05 pm
MXP
-
ORD
1 stop27h 40m
Scandinavian Airlines
Mon 12/77:15 pm
ORD
-
MXP
1 stop32h 15m
Scandinavian Airlines
Deal found 7/27$678
This Mytrip deal was found by Cheapflights users on 7/25. 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 9/239:10 pm
MXP
-
ORD
2 stops25h 00m
Multiple Airlines
Wed 9/309:50 pm
ORD
-
MXP
2 stops16h 10m
Multiple Airlines
Deal found 7/25$679
This Gotogate deal was found by Cheapflights users on 7/28. 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 8/2110:55 pm
MXP
-
ORD
1 stop26h 20m
Icelandair
Sun 9/67:25 pm
ORD
-
MXP
1 stop12h 45m
Icelandair
Deal found 7/28$680
This Icelandair deal was found by Cheapflights users on 7/29. 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 8/1810:55 pm
MXP
-
ORD
1 stop26h 20m
Icelandair
Mon 9/287:25 pm
ORD
-
MXP
1 stop12h 45m
Icelandair
Deal found 7/29$681

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 July 30, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$668
(Icelandair)

One-way from

$362
(Kiwi.com)

Popular in

July

Cheapest in

February

Average price

$1,035

Good round-trip deal

$910 or less

Good one-way deal

$934 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. 16% potential increase in price ($159 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($23 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 July 30, 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 9/2

8:00 pm-4:10 pm

1 stop27h 10m

Chicago O'Hare Intl

Sun 9/6

7:15 pm-7:10 pm

1 stop16h 55m

$675

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Mon 9/21

8:00 pm-4:10 pm

1 stop27h 10m

Chicago O'Hare Intl

Sun 10/11

7:15 pm-7:50 pm

2 stops17h 35m

$683

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Wed 10/28

11:05 am-7:20 pm

1 stop38h 15m

Chicago O'Hare Intl

Wed 11/11

11:45 am-4:50 pm

1 stop22h 05m

$711

BergamoChicago

BGY - ORD

BGYORD

Bergamo Orio Al Serio

Sat 9/5

5:10 pm-1:10 pm

2 stops27h 00m

Chicago O'Hare Intl

Sat 9/19

3:00 pm-12:55 am

2 stops26h 55m

$727

MilanChicago

LIN - ORD

LINORD

Milan Linate

Tue 10/27

12:55 pm-5:45 pm

2 stops34h 50m

Chicago O'Hare Intl

Wed 11/4

7:15 pm-12:05 pm

2 stops33h 50m

$747

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Thu 12/24

11:20 am-4:45 pm

1 stop12h 25m

Chicago O'Hare Intl

Sat 1/2

7:15 pm-8:50 am

1 stop30h 35m

$748

MilanChicago

LIN - ORD

LINORD

Milan Linate

Mon 1/11

6:25 am-11:05 am

1 stop11h 40m

Chicago O'Hare Intl

Sun 1/24

6:04 pm-4:55 pm

2 stops15h 51m

$814

MilanChicago

LIN - ORD

LINORD

Milan Linate

Fri 8/21

6:40 am-2:15 pm

1 stop14h 35m

Chicago O'Hare Intl

Sun 9/6

10:30 am-8:50 am

2 stops15h 20m

$816

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Tue 9/1

3:20 pm-6:10 pm

Nonstop9h 50m

Chicago O'Hare Intl

Sun 9/13

9:35 pm-1:20 pm

Nonstop8h 45m

$816
Quickest round-trip

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Sat 8/22

3:20 pm-6:10 pm

Nonstop9h 50m

Chicago O'Hare Intl

Mon 9/7

9:40 pm-1:20 pm

Nonstop8h 40m

$817

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

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 July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice 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.

Cheapflights Insights

Everything you need to know about your flight from Milan to Chicago

What is the cheapest month to book a flight from Milan to Chicago?

Currently, February is the cheapest month in which you can book a flight from Milan to Chicago (average of $614). Flying from Milan to Chicago in July is currently the most expensive (average of $1,015). 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 July 30, 2026.

When flying from Milan to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Milan to Chicago

Explore weekly flight availability from Milan to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated July 30, 2026.

The most flights from MIL to CHI are scheduled on a Monday (5 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (5 on average).

How much does it cost to fly round-trip from Milan to Chicago?

Airfare is below average for this route at the moment.
Milan to Chicago flights typically cost between $738 and $1,119 in August.
The cheapest round-trip price found within the last 5 days was $668 on Icelandair (Aug 23-Aug 31).

How often are flights from Milan to Chicago delayed?

About 23% of weekly flights between Milan and Chicago have experienced delays in the past year, with the average delay time being 222 minutes.

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

Historically, flights departing in the early afternoon 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 22% of flights being delayed.

How far ahead should I book a flight from Milan to Chicago?

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 35 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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 July 30, 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
10,047 reviews

Boarding

7.7

Comfort

7.3

Food

6.6

Entertainment

7.1

Overall

7.4

Crew

8.1

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
10,047 reviews
United Airlines
7.4
Good
10,047 reviews

Boarding

7.7

Comfort

7.3

Food

6.6

Entertainment

7.1

Overall

7.4

Crew

8.1

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
8,163 reviews
United Airlines
7.4
Good
10,047 reviews

Boarding

7.7

Comfort

7.3

Food

6.6

Entertainment

7.1

Overall

7.4

Crew

8.1

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 Scandinavian Airlines, Turkish Airlines, and United Airlines fly from Milan to Chicago in about 11h 40m. The time it takes to get you to your destination can typically vary by up to 26h 35m. The distance from Milan to Chicago is about 4536 mi. This flight may include one or multiple stops.

  • 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, Bergamo Orio Al Serio - Chicago O'Hare Intl and Milan Malpensa - 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: Air Canada (62%), Austrian Airlines (62%), United Airlines (62%).

  • What are the cheapest flights from Milan to Chicago?

    Looking for the cheapest flight from Milan to Chicago? While on average our users pay $1,817, our data indicates the cheapest price to be $598. The most popular route (Milan Malpensa - Chicago O'Hare Intl), is priced around $515.

  • 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, February is the cheapest month in which you can book a flight from Milan to Chicago (average of $614). Flying from Milan to Chicago in July is currently the most expensive (average of $1,015). 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
Benton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter

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