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

Currently priced at $522, 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. Search Cheapflights for deals from American Airlines and Scandinavian Airlines - these airlines can fly you to your destination from $523 and $528, respectively. British Airways is currently priced 20% below the average price you’ll pay for this route.

What are the cheapest airlines to fly from Milan to Chicago one-way?

$358 is the cheapest one-way deal found within the past few days, from Icelandair. You may also be able to find cheap deals on TAP AIR PORTUGAL and Air Serbia, with prices starting from $402 and $446, respectively.

What is the cheapest day to fly from Milan to Chicago?

Travelers seeking maximum savings on their Milan to Chicago flight should consider departing on Monday at noon when fares are most often at their lowest. Friday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

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 $1,565, our data indicates the cheapest price to be $594. The most popular route (Milan Malpensa - Chicago O'Hare Intl), is priced around $472.

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

Flying to your destination on a Saturday can be more expensive, but this shouldn’t discourage you from finding affordable options to get to Chicago. Check prices with Cheapflights to find a great deal for your trip.

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

Find a great deal and save up to 32% by booking at least 14 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Milan to Chicago within the next two weeks, with the cheapest ticket starting at $490.

What is the cheapest month to fly from Milan to Chicago?

November is one of the best times of the year to fly to Chicago from Milan. Prices for November average $659 per person but you can even find prices for as low as $424. The most expensive prices can be found in the month of July. Opting for a November flight can save you 27% on your journey compared to booking in July

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.

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.

$306+ Flights from Milan to Chicago

Home Search by date Vacation packages Hotels Flight deals Car rental Travel tips & news

Find cheap flights from Milan to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Milan to Chicago are usually found in November or February, booked 13 days in advance, depart on a Saturday or Monday and return on a Tuesday

Cheap flight deals from Milan to Chicago

Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 3 stars
Round-trip from	$522 (lol.travel)
One-way from	$306 (Mytrip)
Popular in	July
Cheapest in	November
Average price	$622
Good round-trip deal	$824 or less
Good one-way deal	$759 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. 18% potential increase in price ($151 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 April 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

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 April 1, 2025.

Thu 4/109:45 pmMXP - ORD

1 stop21h 00mBritish Airways

Thu 4/248:20 pmORD - MXP

1 stop20h 20mBritish Airways

Deal found 3/31

$522

Fri 5/211:10 amMXP - ORD

2 stops19h 39mAmerican Airlines

Fri 5/97:15 pmORD - MXP

1 stop20h 45mAmerican Airlines

Deal found 3/31

$523

Wed 5/217:25 amLIN - ORD

1 stop14h 15mBritish Airways

Tue 5/2710:25 pmORD - LIN

1 stop11h 50mBritish Airways

Deal found 3/31

$525

Tue 5/611:10 amLIN - ORD

1 stop12h 50mAmerican Airlines

Wed 5/144:55 pmORD - LIN

1 stop13h 40mAmerican Airlines

Deal found 3/31

$526

Mon 4/287:25 pmMXP - ORD

1 stop23h 20mMultiple Airlines

Mon 5/59:15 pmORD - MXP

1 stop16h 30mMultiple Airlines

Deal found 4/1

$527

Thu 5/88:45 pmMXP - ORD

2 stops26h 25mScandinavian Airlines

Mon 5/127:15 pmORD - MXP

2 stops17h 40mScandinavian Airlines

Deal found 3/31

$528

Thu 5/1511:10 amMXP - ORD

1 stop13h 24mIberia

Thu 5/2211:45 amORD - MXP

1 stop14h 25mIberia

Deal found 3/30

$531

Thu 5/111:05 amMXP - ORD

1 stop13h 45mFinnair

Wed 5/79:30 pmORD - MXP

1 stop13h 45mFinnair

Deal found 3/31

$546

Thu 4/107:25 amLIN - ORD

1 stop13h 30mMultiple Airlines

Thu 4/174:30 pmORD - LIN

1 stop20h 05mMultiple Airlines

Deal found 3/31

$552

Mon 9/157:00 amLIN - ORD

1 stop13h 10mITA Airways

Sun 9/283:00 pmORD - LIN

1 stop22h 10mITA Airways

Deal found 3/31

$580

Thu 4/107:50 amLIN - ORD

1 stop13h 25mIberia

Sun 4/274:30 pmORD - LIN

1 stop11h 30mIberia

Deal found 3/31

$582

Thu 4/106:40 amLIN - ORD

1 stop14h 30mKLM

Wed 4/234:50 pmORD - LIN

1 stop16h 05mKLM

Deal found 3/31

$597

Best flights from Milan to Chicago
Discover carefully curated flight deals from Milan to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 1, 2025.

Mon 4/287:25 pmMXP - ORD

1 stop23h 20mBritish Airways

Mon 5/59:15 pmORD - MXP

1 stop13h 45mBritish Airways

Deal found 3/31

$522

Fri 5/211:10 amMXP - ORD

2 stops19h 39mAmerican Airlines

Fri 5/97:15 pmORD - MXP

1 stop20h 45mAmerican Airlines

Deal found 3/31

$523

Mon 4/287:25 pmMXP - ORD

1 stop23h 20mMultiple Airlines

Mon 5/59:15 pmORD - MXP

1 stop16h 30mMultiple Airlines

Deal found 4/1

$527

Thu 5/88:45 pmMXP - ORD

2 stops26h 25mScandinavian Airlines

Mon 5/127:15 pmORD - MXP

2 stops17h 40mScandinavian Airlines

Deal found 3/31

$528

Thu 5/1511:10 amMXP - ORD

1 stop13h 24mIberia

Thu 5/2211:45 amORD - MXP

1 stop14h 25mIberia

Deal found 3/30

$531

Thu 5/111:05 amMXP - ORD

1 stop13h 45mFinnair

Wed 5/79:30 pmORD - MXP

1 stop13h 45mFinnair

Deal found 3/31

$546

Mon 9/157:00 amLIN - ORD

1 stop13h 10mITA Airways

Sun 9/283:00 pmORD - LIN

1 stop22h 10mITA Airways

Deal found 3/31

$580

Thu 4/106:40 amLIN - ORD

1 stop14h 30mKLM

Wed 4/234:50 pmORD - LIN

1 stop16h 05mKLM

Deal found 3/31

$597

Sun 5/43:10 pmMXP - ORD

1 stop13h 05mIcelandair

Wed 5/77:25 pmORD - MXP

1 stop11h 45mIcelandair

Deal found 3/31

$604

Thu 4/106:40 amLIN - ORD

1 stop14h 30mDelta

Wed 4/236:15 pmORD - LIN

2 stops12h 40mDelta

Deal found 3/31

$608

Thu 9/187:40 pmMXP - ORD

2 stops26h 15mLOT

Sun 9/215:10 pmORD - MXP

2 stops18h 40mLOT

Deal found 4/1

$611

Sun 4/136:50 amMXP - ORD

1 stop15h 10mAir France

Mon 4/285:10 pmORD - MXP

1 stop13h 45mAir France

Deal found 3/31

$612

Last-minute flights from Milan to Chicago
Discover last-minute flight deals from Milan to Chicago. Data last updated April 1, 2025 and is based on user searches.

Mon 4/711:10 amMXP - ORD

1 stop13h 29mIberia

Mon 4/1411:36 amORD - MXP

1 stop14h 34mIberia

Deal found 4/1

$540

Thu 4/109:45 pmMXP - ORD

1 stop21h 00mBritish Airways

Thu 4/248:20 pmORD - MXP

1 stop20h 20mBritish Airways

Deal found 3/31

$522

Thu 4/109:30 amMXP - ORD

1 stop13h 25mMultiple Airlines

Thu 4/1711:36 amORD - MXP

1 stop14h 34mMultiple Airlines

Deal found 3/31

$539

Thu 4/107:25 amLIN - ORD

1 stop13h 30mMultiple Airlines

Thu 4/174:30 pmORD - LIN

1 stop20h 05mMultiple Airlines

Deal found 3/31

$552

Thu 4/107:35 pmLIN - ORD

1 stop25h 15mBritish Airways

Sun 4/276:30 pmORD - LIN

2 stops15h 45mBritish Airways

Deal found 3/31

$561

Thu 4/107:50 amLIN - ORD

1 stop13h 25mIberia

Sun 4/274:30 pmORD - LIN

1 stop11h 30mIberia

Deal found 3/31

$582

Thu 4/106:40 amLIN - ORD

1 stop14h 30mKLM

Wed 4/234:50 pmORD - LIN

1 stop16h 05mKLM

Deal found 3/31

$597

Thu 4/109:30 amMXP - ORD

1 stop33h 15mAmerican Airlines

Wed 4/238:30 pmORD - MXP

1 stop29h 40mAmerican Airlines

Deal found 4/1

$602

Thu 4/106:40 amLIN - ORD

1 stop14h 30mDelta

Wed 4/236:15 pmORD - LIN

2 stops12h 40mDelta

Deal found 3/31

$608

Thu 4/106:40 amLIN - MDW

2 stops18h 22mDelta

Wed 4/235:59 pmMDW - LIN

2 stops12h 56mDelta

Deal found 3/31

$614

Thu 4/106:50 amMXP - ORD

1 stop15h 10mDelta

Wed 4/235:05 pmORD - MXP

2 stops13h 50mDelta

Deal found 3/31

$614

Thu 4/1010:15 amBGY - ORD

1 stop34h 45mMultiple Airlines

Wed 4/233:45 pmORD - BGY

1 stop25h 20mMultiple Airlines

Deal found 3/31

$616

One-way flights from Milan to Chicago
Search for one-way flight options from Milan to Chicago. Find affordable one-way fares based on user searches. Data last updated April 1, 2025.

Thu 5/87:10 amMXP - ORD

2 stops23h 19mMultiple Airlines

Deal found 3/31

$306

Thu 5/223:30 pmBGY - ORD

2 stops31h 40mMultiple Airlines

Deal found 3/31

$318

Thu 5/224:55 pmLIN - ORD

2 stops30h 15mMultiple Airlines

Deal found 3/31

$330

Thu 5/83:10 pmMXP - ORD

1 stop34h 05mIcelandair

Deal found 3/31

$358

Sun 4/277:10 amMXP - MDW

2 stops36h 21mMultiple Airlines

Deal found 3/31

$381

Fri 6/65:55 amMXP - ORD

1 stop17h 15mTAP AIR PORTUGAL

Deal found 3/31

$402

Sat 4/269:25 amMXP - ORD

1 stop18h 35mAir Serbia

Deal found 3/31

$446

Tue 5/611:05 amMXP - ORD

2 stops37h 24mAir Europa

Deal found 3/31

$465

Wed 4/3011:20 amLIN - ORD

1 stop14h 40mAer Lingus

Deal found 3/31

$493

Wed 4/3010:15 pmMXP - ORD

1 stop22h 45mAer Lingus

Deal found 3/31

$494

Tue 5/67:30 amLIN - ORD

2 stops17h 25mITA Airways

Deal found 3/31

$506

Sun 6/228:10 pmMXP - ORD

1 stop28h 45mTurkish Airlines

Deal found 3/31

$519

Cheapflights Fare Finder

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

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Mon 4/28

7:25 pm-11:45 am

1 stop23h 20m

Chicago O'Hare Intl

Mon 5/5

9:15 pm-6:00 pm

1 stop13h 45m

$522

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Fri 5/2

11:10 am-11:49 pm

2 stops19h 39m

Chicago O'Hare Intl

Fri 5/9

7:15 pm-11:00 pm

1 stop20h 45m

$523

MilanChicago

LIN - ORD

LINORD

Milan Linate

Wed 5/21

7:25 am-2:40 pm

1 stop14h 15m

Chicago O'Hare Intl

Tue 5/27

10:25 pm-5:15 pm

1 stop11h 50m

$525

MilanChicago

LIN - ORD

LINORD

Milan Linate

Tue 5/6

11:10 am-5:00 pm

1 stop12h 50m

Chicago O'Hare Intl

Wed 5/14

4:55 pm-1:35 pm

1 stop13h 40m

$526

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Mon 4/28

7:25 pm-11:45 am

1 stop23h 20m

Chicago O'Hare Intl

Mon 5/5

9:15 pm-8:45 pm

1 stop16h 30m

$527

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Thu 5/8

8:45 pm-4:10 pm

2 stops26h 25m

Chicago O'Hare Intl

Mon 5/12

7:15 pm-7:55 pm

2 stops17h 40m

$528

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Thu 5/15

11:10 am-5:34 pm

1 stop13h 24m

Chicago O'Hare Intl

Thu 5/22

11:45 am-9:10 am

1 stop14h 25m

$531

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Thu 5/1

11:05 am-5:50 pm

1 stop13h 45m

Chicago O'Hare Intl

Sun 5/11

9:30 pm-6:15 pm

1 stop13h 45m

$546

MilanChicago

LIN - ORD

LINORD

Milan Linate

Thu 4/10

7:25 am-1:55 pm

1 stop13h 30m

Chicago O'Hare Intl

Thu 4/17

4:30 pm-7:35 pm

1 stop20h 05m

$552

MilanChicago

LIN - ORD

LINORD

Milan Linate

Mon 9/15

7:00 am-1:10 pm

1 stop13h 10m

Chicago O'Hare Intl

Sun 9/28

3:00 pm-8:10 pm

1 stop22h 10m

$580

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/31

Showing 1-10 of 60 results

...

Compare providers for flights from Milan to Chicago

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Milan to Chicago in April.

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy1 star	Trust Score*3 stars
eDreams	Price Accuracy3 stars	Trust Score*3 stars
AranGrant	Price Accuracy3 stars	Trust Score*1 star
FlightHub	Price Accuracy3 stars	Trust Score*3 stars
Flightnetwork	Price Accuracy-	Trust Score*3 stars
Cheapflightsfares	Price Accuracy3 stars	Trust Score*2 stars
Ovago	Price Accuracy3 stars	Trust 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

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 13 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 $323). 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?

Unlike in the afternoon, when flights are generally more expensive, you can save up to 39% on flights from Milan to Chicago by exploring options for tickets in the evening.

Rainfall in Chicago 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

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 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

8.0

Very good

3,192 reviews

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

8.0

Very good

3,192 reviews

Emirates

8.0

Very good

3,192 reviews

Reviews

1 / 20

2.0

Mediocre

Anonymous,Jun 2024

DXB - IAH

Delta

8.0

Very good

7,899 reviews

Emirates

8.0

Very good

3,192 reviews

Reviews

1 / 20

2.0

Mediocre

Anonymous,Jun 2024

DXB - IAH

KLM

7.8

Good

1,321 reviews

Emirates

8.0

Very good

3,192 reviews

Reviews

1 / 20

2.0

Mediocre

Anonymous,Jun 2024

DXB - IAH

LOT

7.6

Good

1,065 reviews

Emirates

8.0

Very good

3,192 reviews

Reviews

1 / 20

2.0

Mediocre

Anonymous,Jun 2024

DXB - IAH

Finnair

7.6

Good

1,267 reviews

Emirates

8.0

Very good

3,192 reviews

Reviews

1 / 20

2.0

Mediocre

Anonymous,Jun 2024

DXB - IAH

Related info for your journey

What are the cheapest airlines flying from Milan to Chicago round-trip?
Currently priced at $522, 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. Search Cheapflights for deals from American Airlines and Scandinavian Airlines - these airlines can fly you to your destination from $523 and $528, respectively. British Airways is currently priced 20% below the average price you’ll pay for this route.
What are the cheapest airlines to fly from Milan to Chicago one-way?
$358 is the cheapest one-way deal found within the past few days, from Icelandair. You may also be able to find cheap deals on TAP AIR PORTUGAL and Air Serbia, with prices starting from $402 and $446, 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 $1,565, our data indicates the cheapest price to be $594. The most popular route (Milan Malpensa - Chicago O'Hare Intl), is priced around $472.
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 $323). 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

Merrillville

New Buffalo

Hammond

Benton Harbor

Porter

Lansing

Valparaiso

Chesterton

Browse thousands of different options on Cheapflights for your next trip

Top 2 airlines flying from Milan to Chicago

Airline	Cheapest	Average	Flexibility	On-time
TAP AIR PORTUGAL	Cheapest$537	Average$564	FlexibilityNo cancel fee	On-timeN/A
United Airlines	Cheapest$625	Average$864	FlexibilityNo cancel fee	On-time69%

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$306+ 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 5/8. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Milan to Chicago with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheapflights Tip: The best prices from Milan to Chicago are usually found in November or February, booked 13 days in advance, depart on a Saturday or Monday and return on a Tuesday

Cheap flight deals from Milan to Chicago

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Good round-trip deal

Good one-way deal

Find flight deals from Milan to Chicago

Cheapest flights from Milan to ChicagoExplore 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 April 1, 2025.

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 April 1, 2025.

Cheapflights Fare Finder

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

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 April.

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.

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 28, 2025.

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

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 April 1, 2025.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

Reviews of airlines servicing Chicago

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.

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?

What are the cheapest airlines to fly from Milan to Chicago one-way?

What are the most popular routes from Milan to Chicago?

What are the cheapest flights from Milan to Chicago?

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Alternative routes for Milan to Chicago

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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 April 1, 2025.