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$284+ 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 2/10. Fares are subject to change and may not be available on all flights or dates of travel.
MIL — CHI
Jan 3 — Jan 101
Sat 1/3
Sat 1/10
1 adult, Economy
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Find cheap flights from Milan to Chicago with Cheapflights

1. Tell us where you want to go

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Cheapflights Tip: The best prices from Milan to Chicago are usually found in February or March, booked 38 days in advance, depart on a Tuesday or Wednesday 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 December 4, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 12/2. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/176:20 amMXP - ORD
1 stop15h 40mTAP AIR PORTUGAL
Wed 12/317:10 pmORD - MXP
1 stop14h 45mTAP AIR PORTUGAL
Deal found 12/2$629
This Mytrip deal was found by Cheapflights users on 12/2. 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.
Sun 12/145:45 pmMXP - ORD
2 stops35h 26mMultiple Airlines
Tue 12/306:30 pmORD - MXP
2 stops19h 15mMultiple Airlines
Deal found 12/2$638
This lol.travel deal was found by Cheapflights users on 12/2. 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 12/258:00 pmMXP - ORD
1 stop27h 45mScandinavian Airlines
Mon 1/57:20 pmORD - MXP
1 stop30h 05mScandinavian Airlines
Deal found 12/2$639
This Mytrip deal was found by Cheapflights users on 12/4. 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 12/235:45 amBGY - ORD
1 stop15h 15mMultiple Airlines
Tue 12/307:40 pmORD - BGY
1 stop20h 25mMultiple Airlines
Deal found 12/4$664
This deal was found by Cheapflights users on 12/3. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/176:20 amMXP - ORD
1 stop15h 40mTAP AIR PORTUGAL
Fri 1/168:15 pmORD - MXP
1 stop13h 40mTAP AIR PORTUGAL
Deal found 12/3$681
This Cheapflightsfares deal was found by Cheapflights users on 12/2. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/177:30 amLIN - ORD
2 stops17h 50mITA Airways
Wed 12/319:20 amORD - LIN
2 stops17h 50mITA Airways
Deal found 12/2$694
This Mytrip deal was found by Cheapflights users on 12/3. 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 12/113:15 pmBGY - ORD
2 stops30h 45mMultiple Airlines
Wed 1/216:30 pmORD - BGY
2 stops16h 45mMultiple Airlines
Deal found 12/3$695
This deal was found by Cheapflights users on 12/3. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/179:45 amMXP - ORD
1 stop15h 29mUnited Airlines
Tue 1/1310:52 amORD - MXP
1 stop13h 38mUnited Airlines
Deal found 12/3$705
This Mytrip deal was found by Cheapflights users on 12/4. 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 12/235:45 pmMXP - ORD
1 stop28h 15mMultiple Airlines
Tue 12/306:30 pmORD - MXP
2 stops19h 15mMultiple Airlines
Deal found 12/4$723
This Gotogate deal was found by Cheapflights users on 12/2. 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 12/57:25 amLIN - ORD
1 stop15h 00mBritish Airways
Mon 12/88:35 pmORD - LIN
1 stop12h 45mBritish Airways
Deal found 12/2$777
This American Airlines deal was found by Cheapflights users on 12/2. 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.
Fri 12/57:25 amLIN - ORD
1 stop15h 00mAmerican Airlines
Tue 12/96:35 pmORD - LIN
1 stop12h 55mAmerican Airlines
Deal found 12/2$779
This FlightHub deal was found by Cheapflights users on 12/4. 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.
Wed 12/1711:45 amLIN - ORD
1 stop13h 10mAer Lingus
Wed 12/313:50 pmORD - LIN
1 stop12h 15mAer Lingus
Deal found 12/4$781

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 December 4, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$572
(Mytrip)

One-way from

$284
(Kiwi.com)

Popular in

July

Cheapest in

February

Average price

$732

Good round-trip deal

$690 or less

Good one-way deal

$816 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 ($134 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($21 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 December 4, 2025.
Use the filters below to find and compare flights from Milan to Chicago that are best for you.

Fly from

Milan

Fly to

Chicago

Route

Depart

Return

Price

BergamoChicago

BGY - ORD

BGYORD

Bergamo Orio Al Serio

Tue 1/13

2:35 pm-3:10 pm

2 stops31h 35m

Chicago O'Hare Intl

Wed 1/28

4:25 pm-10:10 pm

2 stops22h 45m

$572

BergamoChicago

BGY - ORD

BGYORD

Bergamo Orio Al Serio

Fri 1/16

11:25 am-7:15 pm

1 stop14h 50m

Chicago O'Hare Intl

Fri 1/23

9:00 pm-9:20 pm

1 stop17h 20m

$572

BergamoChicago

BGY - ORD

BGYORD

Bergamo Orio Al Serio

Thu 1/22

5:45 am-5:20 pm

2 stops18h 35m

Chicago O'Hare Intl

Sat 2/7

6:30 pm-6:25 pm

2 stops16h 55m

$588

BergamoChicago

BGY - ORD

BGYORD

Bergamo Orio Al Serio

Tue 2/10

5:45 am-5:20 pm

2 stops18h 35m

Chicago O'Hare Intl

Tue 4/14

7:25 pm-9:05 pm

2 stops18h 40m

$601

BergamoChicago

BGY - ORD

BGYORD

Bergamo Orio Al Serio

Thu 1/15

10:35 pm-3:25 pm

2 stops23h 50m

Chicago O'Hare Intl

Wed 1/28

6:30 pm-6:15 pm

2 stops16h 45m

$620

BergamoChicago

BGY - ORD

BGYORD

Bergamo Orio Al Serio

Thu 1/15

10:35 pm-3:25 pm

2 stops23h 50m

Chicago O'Hare Intl

Sun 1/25

6:30 pm-11:59 pm

2 stops22h 29m

$621

BergamoChicago

BGY - ORD

BGYORD

Bergamo Orio Al Serio

Sat 1/17

2:40 pm-2:45 pm

2 stops31h 05m

Chicago O'Hare Intl

Sat 1/24

6:30 pm-6:25 pm

2 stops16h 55m

$621

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Tue 2/17

8:00 pm-4:45 pm

1 stop27h 45m

Chicago O'Hare Intl

Sat 3/14

8:20 pm-7:10 pm

1 stop16h 50m

$625

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Wed 5/20

9:05 am-2:50 pm

1 stop12h 45m

Chicago O'Hare Intl

Mon 6/1

1:10 pm-10:20 am

1 stop14h 10m

$628

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Fri 1/16

9:10 am-3:20 pm

1 stop13h 10m

Chicago O'Hare Intl

Sun 1/18

10:50 am-8:20 am

2 stops14h 30m

$629

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/2

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*
eDreamsPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
OvagoPrice Accuracy2 starsTrust Score*2 stars
AranGrantPrice 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Milan-Chicago flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 November 28, 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 38 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 $461). Flying from Milan to Chicago in January is currently the most expensive (average of $868). 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 4, 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 morning.

How often are flights from Milan to Chicago delayed?

About 18% of weekly flights between Milan and Chicago have experienced delays in the past year, with the average delay time being 196 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, Qatar Airways have had the lowest number of delays on this route, with just 17% 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
Airports
MXP

For a quick departure at MXP, consider purchasing fast track security access online, available in both terminals.

Read more about MXPby Ramsey Qubein
ORD

Expect long walks to immigration at ORD's Terminal 5. Be prepared for extensive lines upon arrival.

Read more about ORDby Ramsey Qubein
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD and MXP

Ramsey Qubein

Ramsey Qubein

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 December 4, 2025.
Get a feel of what it's like to fly with United Airlines, Lufthansa, and British Airways 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
9,064 reviews

Comfort

7.3

Crew

8.1

Boarding

7.7

Entertainment

7.1

Overall

7.4

Food

6.6

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.
United Airlines
7.4
Good
9,064 reviews
United Airlines
7.4
Good
9,064 reviews

Comfort

7.3

Crew

8.1

Boarding

7.7

Entertainment

7.1

Overall

7.4

Food

6.6

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.
Lufthansa
6.8
Okay
7,612 reviews
United Airlines
7.4
Good
9,064 reviews

Comfort

7.3

Crew

8.1

Boarding

7.7

Entertainment

7.1

Overall

7.4

Food

6.6

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.
British Airways
6.7
Okay
7,559 reviews
United Airlines
7.4
Good
9,064 reviews

Comfort

7.3

Crew

8.1

Boarding

7.7

Entertainment

7.1

Overall

7.4

Food

6.6

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.

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, United Airlines, and Delta fly from Milan to Chicago in about 12h 45m. The time it takes to get you to your destination can typically vary by up to 15h. The distance from Milan to Chicago is about 4508 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Milan to Chicago round-trip?

    Currently priced at $525, British Airways will fly you from Milan to Chicago and back. In addition to British Airways, many other airlines offer competitively priced options for your trip. Check Cheapflights for deals on United Airlines for as low as $672. British Airways is currently priced 24% 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 Midway 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: Air Canada (85%), Austrian Airlines (85%), United Airlines (85%).

  • What are the cheapest flights from Milan to Chicago?

    Looking for the cheapest flight from Milan to Chicago? While on average our users pay $813, our data indicates the cheapest price to be $641. The most popular route (Milan Malpensa - Chicago O'Hare Intl), is priced around $439.

  • 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 $461). Flying from Milan to Chicago in January is currently the most expensive (average of $868). 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

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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
Verona to O'Hare Intl flights
Malpensa to Moline flights
Malpensa to St. Louis flights

Top 2 airlines flying from Milan to Chicago

Discover the top 2 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 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
British AirwaysCheapest$525Average$716FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$672Average$1,110FlexibilityNo cancel feeOn-time69%

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