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$315+ 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 8/29. Fares are subject to change and may not be available on all flights or dates of travel.
MIL — CHI
Jul 12 — Jul 191
Sun 7/12
Sun 7/19
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 November, booked 63 days in advance, depart on a Tuesday or Saturday and return on a Monday

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 June 12, 2026.

This FlightHub deal was found by Cheapflights users on 6/7. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/244:20 pm
MXP
-
ORD
1 stop12h 05m
Icelandair
Mon 8/317:25 pm
ORD
-
MXP
1 stop19h 30m
Icelandair
Deal found 6/7$540
This lol.travel deal was found by Cheapflights users on 6/8. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/159:00 pm
LIN
-
ORD
1 stop23h 10m
ITA Airways
Sun 6/283:00 pm
ORD
-
LIN
1 stop13h 40m
ITA Airways
Deal found 6/8$546
This lol.travel deal was found by Cheapflights users on 6/7. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/910:00 am
MXP
-
ORD
1 stop16h 15m
JetBlue
Wed 7/2210:56 am
ORD
-
MXP
1 stop14h 14m
JetBlue
Deal found 6/7$547
This oojo deal was found by Cheapflights users on 6/7. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/234:20 pm
MXP
-
ORD
1 stop32h 55m
Icelandair
Mon 8/3110:25 pm
ORD
-
MXP
1 stop16h 30m
Icelandair
Deal found 6/7$573
This Gotogate deal was found by Cheapflights users on 6/10. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/314:20 pm
MXP
-
ORD
1 stop12h 05m
Icelandair
Mon 9/710:25 pm
ORD
-
MXP
1 stop16h 30m
Icelandair
Deal found 6/10$580
This Mytrip deal was found by Cheapflights users on 6/9. 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 9/410:55 pm
MXP
-
ORD
1 stop26h 20m
Icelandair
Sat 9/197:25 pm
ORD
-
MXP
1 stop12h 45m
Icelandair
Deal found 6/9$581
This Mytrip deal was found by Cheapflights users on 6/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/319:45 pm
BGY
-
ORD
2 stops30h 40m
Multiple Airlines
Mon 9/77:25 pm
ORD
-
BGY
2 stops19h 25m
Multiple Airlines
Deal found 6/10$586
This Mytrip deal was found by Cheapflights users on 6/9. 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 9/169:00 pm
LIN
-
ORD
1 stop23h 10m
ITA Airways
Wed 9/233:00 pm
ORD
-
LIN
1 stop12h 10m
ITA Airways
Deal found 6/9$592
This ITA Airways deal was found by Cheapflights users on 6/8. 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 ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/267:00 am
LIN
-
ORD
1 stop13h 10m
ITA Airways
Wed 9/303:00 pm
ORD
-
LIN
1 stop13h 40m
ITA Airways
Deal found 6/8$593
This Cheapflightsfares deal was found by Cheapflights users on 6/8. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/710:00 am
MXP
-
ORD
1 stop16h 31m
JetBlue
Tue 7/1410:56 am
ORD
-
MXP
1 stop14h 14m
JetBlue
Deal found 6/8$593
This lol.travel deal was found by Cheapflights users on 6/11. 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 11/2711:20 am
MXP
-
ORD
1 stop12h 25m
Scandinavian Airlines
Thu 12/37:15 pm
ORD
-
MXP
1 stop17h 00m
Scandinavian Airlines
Deal found 6/11$598
This lol.travel deal was found by Cheapflights users on 6/8. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/127:00 am
LIN
-
ORD
1 stop13h 10m
ITA Airways
Sat 9/193:00 pm
ORD
-
LIN
1 stop13h 40m
ITA Airways
Deal found 6/8$602

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 June 12, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$540
(FlightHub)

One-way from

$315

Popular in

July

Cheapest in

February

Average price

$832

Good round-trip deal

$658 or less

Good one-way deal

$842 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 ($149 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($25 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 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 June 12, 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

LIN - ORD

LINORD

Milan Linate

Sat 9/26

7:00 am-1:10 pm

1 stop13h 10m

Chicago O'Hare Intl

Tue 9/29

3:00 pm-11:40 am

1 stop13h 40m

$593

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Mon 9/21

11:05 am-9:12 pm

1 stop17h 07m

Chicago O'Hare Intl

Sun 10/11

5:55 pm-1:20 pm

1 stop12h 25m

$700

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Fri 11/27

12:50 pm-6:45 pm

1 stop12h 55m

Chicago O'Hare Intl

Tue 12/8

9:45 pm-7:45 pm

1 stop15h 00m

$702

MilanChicago

LIN - MDW

LINMDW

Milan Linate

Fri 10/9

6:40 am-4:50 pm

2 stops17h 10m

Chicago Midway

Mon 10/12

1:00 pm-11:20 am

2 stops15h 20m

$703

MilanChicago

LIN - ORD

LINORD

Milan Linate

Sun 10/18

6:40 am-2:15 pm

1 stop14h 35m

Chicago O'Hare Intl

Mon 10/26

1:35 pm-11:15 am

2 stops15h 40m

$708

MilanChicago

LIN - MDW

LINMDW

Milan Linate

Sun 10/18

6:40 am-6:37 pm

2 stops18h 57m

Chicago Midway

Mon 10/26

5:25 pm-1:55 pm

2 stops14h 30m

$713

MilanChicago

LIN - MDW

LINMDW

Milan Linate

Fri 11/27

6:30 am-4:25 pm

2 stops16h 55m

Chicago Midway

Thu 12/3

1:00 pm-11:15 am

2 stops15h 15m

$714

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Mon 9/21

11:35 am-6:33 pm

1 stop13h 58m

Chicago O'Hare Intl

Sun 10/11

5:45 pm-2:45 pm

2 stops14h 00m

$714

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Sat 10/31

6:55 am-6:37 pm

2 stops17h 42m

Chicago Midway

Sun 11/8

1:00 pm-11:40 am

2 stops15h 40m

$717

MilanChicago

LIN - ORD

LINORD

Milan Linate

Fri 9/25

6:40 am-4:14 pm

2 stops16h 34m

Chicago O'Hare Intl

Sat 10/3

10:35 am-10:05 am

2 stops16h 30m

$719

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/12

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 June.
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, September is the cheapest month in which you can book a flight from Milan to Chicago (average of $356). Flying from Milan to Chicago in July is currently the most expensive (average of $635). 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 June 12, 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 June 12, 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?

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.

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 57 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 June 12, 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
9,804 reviews

Overall

7.4

Food

6.6

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Crew

8.1

Reviews

1 / 20
4.0
Okay

Dynasty,May 2026

LAX - EWR

The food wasn’t nice - Hosts were not that kind.
United Airlines
7.4
Good
9,804 reviews
United Airlines
7.4
Good
9,804 reviews

Overall

7.4

Food

6.6

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Crew

8.1

Reviews

1 / 20
4.0
Okay

Dynasty,May 2026

LAX - EWR

The food wasn’t nice - Hosts were not that kind.
Lufthansa
6.8
Okay
8,052 reviews
United Airlines
7.4
Good
9,804 reviews

Overall

7.4

Food

6.6

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Crew

8.1

Reviews

1 / 20
4.0
Okay

Dynasty,May 2026

LAX - EWR

The food wasn’t nice - Hosts were not that kind.

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 British Airways and Delta fly from Milan to Chicago in about 17h 07m. The time it takes to get you to your destination can typically vary by up to 03m. The distance from Milan to Chicago is about 4508 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, Milan Linate - 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: Brussels Airlines (75%), Air Canada (71%), Austrian Airlines (71%).

  • What are the cheapest flights from Milan to Chicago?

    Looking for the cheapest flight from Milan to Chicago? While on average our users pay $803, our data indicates the cheapest price to be $585. The most popular route (Milan Malpensa - Chicago O'Hare Intl), is priced around $558.

  • 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, September is the cheapest month in which you can book a flight from Milan to Chicago (average of $356). Flying from Milan to Chicago in July is currently the most expensive (average of $635). 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
Hammond
Porter

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