How long is the flight from Milan to Chicago?

Airlines like Scandinavian Airlines, ITA Airways, and United Airlines fly from Milan to Chicago in about 12h 30m. The time it takes to get you to your destination can typically vary by up to 12h 40m. 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 $626. British Airways is currently priced 23% below the average price you’ll pay for this route.

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.

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).

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 $2,019, our data indicates the cheapest price to be $632. The most popular route (Milan Malpensa - Chicago O'Hare Intl), is priced around $500.

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: Qatar Airways (77%), Air Canada (75%), Austrian Airlines (75%).

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.

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.

Cheap Flights from Milan, Italy to Chicago, IL from $310 - MIL to CHI Tickets & Airfare Deals at Cheapflights.com

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

Airfare is typical for this route at the moment. Milan to Chicago flights typically cost between $510 and $701 in November. The cheapest round-trip price found within the last 3 days was $562 on Multiple Airlines (Nov 12-Nov 16).

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

Cheap flight deals from Milan to Chicago

Most accurate provider	eDreams 3 stars
Most trusted provider	eDreams 3 stars
Round-trip from	$562 (Mytrip)
One-way from	$295 (Kiwi.com)
Popular in	July
Cheapest in	February
Average price	$675
Good round-trip deal	$752 or less
Good one-way deal	$706 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. 17% potential increase in price ($140 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 October 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 October 29, 2025.

Wed 11/1211:10 amBGY - ORD

1 stop13h 45mMultiple Airlines

Sun 11/163:50 pmORD - BGY

1 stop12h 10mMultiple Airlines

Deal found 10/27

$562

Thu 11/133:55 pmBGY - ORD

2 stops29h 05mMultiple Airlines

Mon 11/176:50 pmORD - BGY

2 stops16h 50mMultiple Airlines

Deal found 10/28

$565

Wed 11/198:00 pmMXP - ORD

1 stop27h 45mScandinavian Airlines

Sat 11/297:20 pmORD - MXP

1 stop16h 50mScandinavian Airlines

Deal found 10/27

$589

Fri 11/76:10 amLIN - ORD

1 stop14h 00mLufthansa

Sun 11/2310:35 pmORD - LIN

1 stop12h 35mLufthansa

Deal found 10/28

$590

Fri 11/73:05 pmMXP - ORD

Nonstop10h 00mLufthansa

Sun 11/239:35 pmORD - MXP

Nonstop8h 30mLufthansa

Deal found 10/28

$590

Tue 11/113:00 pmMXP - ORD

2 stops30h 00mMultiple Airlines

Tue 11/186:50 pmORD - MXP

2 stops18h 55mMultiple Airlines

Deal found 10/28

$592

Fri 12/52:35 pmMXP - ORD

2 stops32h 45mMultiple Airlines

Mon 12/84:20 pmORD - MXP

3 stops20h 10mMultiple Airlines

Deal found 10/28

$596

Fri 11/711:15 amMXP - ORD

1 stop12h 30mScandinavian Airlines

Sun 11/237:20 pmORD - MXP

1 stop16h 50mScandinavian Airlines

Deal found 10/28

$598

Fri 11/711:15 amMXP - ORD

1 stop12h 30mScandinavian Airlines

Sat 11/227:20 pmORD - MXP

1 stop16h 50mScandinavian Airlines

Deal found 10/26

$599

Thu 11/2011:45 amLIN - ORD

1 stop13h 10mAer Lingus

Thu 11/273:50 pmORD - LIN

1 stop12h 15mAer Lingus

Deal found 10/27

$602

Wed 11/261:00 pmMXP - ORD

2 stops34h 45mScandinavian Airlines

Sat 11/297:20 pmORD - MXP

1 stop16h 50mScandinavian Airlines

Deal found 10/27

$603

Wed 12/31:00 pmMXP - ORD

2 stops34h 45mScandinavian Airlines

Wed 12/107:20 pmORD - MXP

1 stop16h 50mScandinavian Airlines

Deal found 10/28

$604

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 October 29, 2025.

Thu 11/133:55 pmBGY - ORD

2 stops29h 05mMultiple Airlines

Mon 11/176:50 pmORD - BGY

2 stops16h 50mMultiple Airlines

Deal found 10/28

$565

Fri 11/2111:15 amMXP - ORD

1 stop12h 30mScandinavian Airlines

Sat 11/297:20 pmORD - MXP

1 stop16h 50mScandinavian Airlines

Deal found 10/27

$589

Fri 11/76:55 amMXP - ORD

1 stop13h 15mLufthansa

Sun 11/239:35 pmORD - MXP

Nonstop8h 30mLufthansa

Deal found 10/26

$634

Thu 4/237:00 pmLIN - ORD

1 stop25h 10mITA Airways

Wed 4/293:00 pmORD - LIN

1 stop12h 10mITA Airways

Deal found 10/27

$637

Fri 11/711:30 amMXP - ORD

2 stops19h 13mUnited Airlines

Tue 11/259:35 pmORD - MXP

Nonstop8h 30mUnited Airlines

Deal found 10/26

$639

Thu 11/206:00 amLIN - ORD

2 stops15h 55mAir Canada

Thu 11/2712:50 pmORD - LIN

2 stops16h 05mAir Canada

Deal found 10/27

$649

Thu 2/127:15 amLIN - ORD

1 stop16h 45mBritish Airways

Sun 2/159:45 pmORD - LIN

1 stop11h 35mBritish Airways

Deal found 10/27

$661

Wed 11/1212:00 pmMXP - MDW

2 stops18h 40mDelta

Sun 11/1612:47 pmMDW - MXP

2 stops14h 48mDelta

Deal found 10/27

$665

Wed 2/1111:05 amMXP - MDW

1 stop18h 21mAir France

Wed 2/181:05 pmMDW - MXP

1 stop13h 00mAir France

Deal found 10/27

$704

Thu 2/266:30 amLIN - MDW

2 stops16h 55mKLM

Sat 3/71:00 pmMDW - LIN

2 stops14h 00mKLM

Deal found 10/27

$719

Wed 12/31:00 pmMXP - ORD

2 stops34h 45mScandinavian Airlines

Wed 12/107:20 pmORD - MXP

1 stop16h 50mScandinavian Airlines

Deal found 10/28

$604

Tue 11/112:35 pmBGY - ORD

2 stops30h 25mMultiple Airlines

Tue 11/186:50 pmORD - BGY

2 stops19h 50mMultiple Airlines

Deal found 10/28

$612

Fri 4/247:00 amLIN - ORD

1 stop13h 10mITA Airways

Wed 4/293:00 pmORD - LIN

1 stop12h 10mITA Airways

Deal found 10/27

$637

Sat 11/156:10 amLIN - ORD

1 stop16h 10mUnited Airlines

Sat 11/297:15 amORD - LIN

2 stops23h 50mUnited Airlines

Deal found 10/28

$641

Mon 2/96:55 pmLIN - ORD

1 stop29h 05mBritish Airways

Sun 2/159:45 pmORD - LIN

1 stop13h 00mBritish Airways

Deal found 10/27

$661

Fri 12/56:30 amLIN - MDW

2 stops18h 30mDelta

Mon 12/81:14 pmMDW - LIN

2 stops15h 01mDelta

Deal found 10/27

$667

Wed 11/58:00 pmMXP - ORD

1 stop27h 45mScandinavian Airlines

Sat 11/227:20 pmORD - MXP

1 stop16h 50mScandinavian Airlines

Deal found 10/26

$623

Fri 11/710:40 amMXP - ORD

1 stop12h 40mUnited Airlines

Sun 11/239:35 pmORD - MXP

Nonstop8h 30mUnited Airlines

Deal found 10/28

$641

Fri 1/166:55 amMXP - MDW

2 stops22h 14mAir France

Fri 1/3012:48 pmMDW - MXP

2 stops15h 52mAir France

Deal found 10/29

$715

Tue 11/119:30 pmLIN - ORD

2 stops27h 40mITA Airways

Wed 11/199:20 amORD - LIN

2 stops20h 20mITA Airways

Deal found 10/26

$651

Fri 12/56:30 amLIN - ORD

1 stop14h 50mMultiple Airlines

Mon 12/85:20 pmORD - LIN

1 stop10h 55mMultiple Airlines

Deal found 10/27

$661

Fri 2/136:55 pmLIN - ORD

1 stop29h 05mBritish Airways

Sat 2/215:10 pmORD - LIN

1 stop13h 15mBritish Airways

Deal found 10/27

$661

Sat 11/156:30 amLIN - MDW

2 stops18h 38mDelta

Sat 11/291:15 pmMDW - LIN

2 stops15h 00mDelta

Deal found 10/27

$667

Wed 1/1412:55 pmMXP - ORD

2 stops34h 50mScandinavian Airlines

Fri 2/277:20 pmORD - MXP

2 stops15h 15mScandinavian Airlines

Deal found 10/28

$625

Thu 11/610:40 amMXP - ORD

1 stop12h 40mUnited Airlines

Tue 11/259:35 pmORD - MXP

Nonstop8h 30mUnited Airlines

Deal found 10/26

$643

Tue 2/1011:25 amLIN - ORD

1 stop12h 35mBritish Airways

Thu 2/199:45 pmORD - LIN

1 stop11h 35mBritish Airways

Deal found 10/27

$661

Thu 11/2710:55 amLIN - MDW

2 stops19h 45mDelta

Sun 12/710:49 amMDW - LIN

2 stops14h 56mDelta

Deal found 10/27

$667

Sun 11/912:55 pmBGY - ORD

2 stops33h 15mMultiple Airlines

Tue 11/255:20 pmORD - BGY

2 stops21h 20mMultiple Airlines

Deal found 10/27

$680

Fri 1/98:00 pmMXP - ORD

1 stop27h 45mScandinavian Airlines

Fri 1/167:20 pmORD - MXP

1 stop30h 05mScandinavian Airlines

Deal found 10/29

$625

Thu 11/206:00 amLIN - ORD

1 stop12h 10mUnited Airlines

Thu 11/275:55 pmORD - LIN

1 stop11h 00mUnited Airlines

Deal found 10/27

$649

Last-minute flights from Milan to Chicago
Discover last-minute flight deals from Milan to Chicago. Data last updated October 29, 2025 and is based on user searches.

Fri 11/76:10 amLIN - ORD

1 stop14h 00mLufthansa

Sun 11/2310:35 pmORD - LIN

1 stop12h 35mLufthansa

Deal found 10/28

$590

Fri 11/73:05 pmMXP - ORD

Nonstop10h 00mLufthansa

Sun 11/239:35 pmORD - MXP

Nonstop8h 30mLufthansa

Deal found 10/28

$590

Fri 11/711:15 amMXP - ORD

1 stop12h 30mScandinavian Airlines

Sun 11/237:20 pmORD - MXP

1 stop16h 50mScandinavian Airlines

Deal found 10/29

$596

Fri 11/711:15 amMXP - ORD

1 stop12h 30mScandinavian Airlines

Sun 11/237:20 pmORD - MXP

1 stop16h 50mScandinavian Airlines

Deal found 10/28

$598

Fri 11/711:15 amMXP - ORD

1 stop12h 30mScandinavian Airlines

Sat 11/227:20 pmORD - MXP

1 stop16h 50mScandinavian Airlines

Deal found 10/26

$599

Tue 11/113:00 pmMXP - ORD

2 stops30h 00mMultiple Airlines

Tue 11/186:50 pmORD - MXP

2 stops18h 55mMultiple Airlines

Deal found 10/28

$592

Wed 11/1211:10 amBGY - ORD

1 stop13h 45mMultiple Airlines

Sun 11/163:50 pmORD - BGY

1 stop12h 10mMultiple Airlines

Deal found 10/27

$562

Wed 11/1210:35 amMXP - ORD

2 stops16h 25mAir Canada

Sun 11/1612:50 pmORD - MXP

1 stop14h 05mAir Canada

Deal found 10/27

$607

Thu 11/133:55 pmBGY - ORD

2 stops29h 05mMultiple Airlines

Mon 11/176:50 pmORD - BGY

2 stops16h 50mMultiple Airlines

Deal found 10/28

$565

Wed 11/1911:15 amMXP - ORD

1 stop12h 30mScandinavian Airlines

Fri 11/287:20 pmORD - MXP

1 stop32h 05mScandinavian Airlines

Deal found 10/27

$589

Thu 11/2011:45 amLIN - ORD

1 stop13h 10mAer Lingus

Thu 11/273:50 pmORD - LIN

1 stop12h 15mAer Lingus

Deal found 10/27

$602

Wed 11/261:00 pmMXP - ORD

2 stops34h 45mScandinavian Airlines

Sat 11/297:20 pmORD - MXP

1 stop16h 50mScandinavian Airlines

Deal found 10/27

$603

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 October 29, 2025.

Fri 1/3010:20 pmBGY - ORD

2 stops45h 37mMultiple Airlines

Deal found 10/28

$310

Fri 1/3010:25 pmBGY - ORD

3 stops45h 32mMultiple Airlines

Deal found 10/28

$337

Thu 12/119:55 pmMXP - ORD

2 stops24h 30mMultiple Airlines

Deal found 10/27

$341

Mon 12/89:35 pmBGY - ORD

3 stops48h 22mMultiple Airlines

Deal found 10/27

$344

Mon 1/198:20 amMXP - ORD

2 stops37h 35mMultiple Airlines

Deal found 10/27

$346

Wed 12/109:55 pmMXP - ORD

3 stops48h 02mMultiple Airlines

Deal found 10/27

$348

Wed 12/106:40 pmMXP - ORD

2 stops51h 17mMultiple Airlines

Deal found 10/27

$352

Mon 1/199:30 pmBGY - ORD

2 stops24h 25mMultiple Airlines

Deal found 10/27

$352

Mon 12/89:30 pmLIN - ORD

2 stops48h 27mMultiple Airlines

Deal found 10/27

$357

Thu 12/119:50 amMXP - ORD

3 stops36h 07mMultiple Airlines

Deal found 10/27

$357

Sat 12/69:55 pmMXP - ORD

2 stops23h 50mMultiple Airlines

Deal found 10/27

$358

Wed 12/1010:05 pmBGY - ORD

3 stops47h 52mMultiple Airlines

Deal found 10/27

$358

Fly from

Fly to

Route

Depart

Return

Price

BergamoChicago

BGY - ORD

BGYORD

Bergamo Orio Al Serio

Thu 11/13

3:55 pm-2:00 pm

2 stops29h 05m

Chicago O'Hare Intl

Mon 11/17

6:50 pm-6:40 pm

2 stops16h 50m

$565

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Fri 11/21

11:15 am-4:45 pm

1 stop12h 30m

Chicago O'Hare Intl

Sat 11/29

7:20 pm-7:10 pm

1 stop16h 50m

$589

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Wed 12/3

1:00 pm-4:45 pm

2 stops34h 45m

Chicago O'Hare Intl

Wed 12/10

7:20 pm-7:10 pm

1 stop16h 50m

$604

BergamoChicago

BGY - ORD

BGYORD

Bergamo Orio Al Serio

Tue 11/11

2:35 pm-2:00 pm

2 stops30h 25m

Chicago O'Hare Intl

Tue 11/18

6:50 pm-9:40 pm

2 stops19h 50m

$612

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Wed 11/5

8:00 pm-4:45 pm

1 stop27h 45m

Chicago O'Hare Intl

Sat 11/22

7:20 pm-7:10 pm

1 stop16h 50m

$623

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Wed 1/14

12:55 pm-4:45 pm

2 stops34h 50m

Chicago O'Hare Intl

Fri 2/27

7:20 pm-5:35 pm

2 stops15h 15m

$625

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Fri 1/9

8:00 pm-4:45 pm

1 stop27h 45m

Chicago O'Hare Intl

Fri 1/16

7:20 pm-8:25 am

1 stop30h 05m

$625

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Fri 11/7

6:55 am-1:10 pm

1 stop13h 15m

Chicago O'Hare Intl

Sun 11/23

9:35 pm-1:05 pm

Nonstop8h 30m

$634

MilanChicago

LIN - ORD

LINORD

Milan Linate

Thu 4/23

7:00 pm-1:10 pm

1 stop25h 10m

Chicago O'Hare Intl

Wed 4/29

3:00 pm-10:10 am

1 stop12h 10m

$637

MilanChicago

LIN - ORD

LINORD

Milan Linate

Fri 4/24

7:00 am-1:10 pm

1 stop13h 10m

Chicago O'Hare Intl

Wed 4/29

3:00 pm-10:10 am

1 stop12h 10m

$637

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

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 October.

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy2 stars	Trust Score*3 stars
eDreams	Price Accuracy3 stars	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*1 star
Ovago	Price Accuracy2 stars	Trust Score*2 stars
AranGrant	Price Accuracy2 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 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?

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, November is the cheapest month in which you can book a flight from Milan to Chicago (average of $484). 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?

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

Reviews of airlines servicing Chicago

Get a feel of what it's like to fly with United Airlines, Aer Lingus, 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

9,001 reviews

Reviews

1 / 20

2.0

Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000

United Airlines

7.4

Good

9,001 reviews

United Airlines

7.4

Good

9,001 reviews

Reviews

1 / 20

2.0

Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000

Aer Lingus

7.2

Good

1,361 reviews

United Airlines

7.4

Good

9,001 reviews

Reviews

1 / 20

2.0

Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000

Lufthansa

6.8

Okay

7,539 reviews

United Airlines

7.4

Good

9,001 reviews

Reviews

1 / 20

2.0

Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000

British Airways

6.7

Okay

7,485 reviews

United Airlines

7.4

Good

9,001 reviews

Reviews

1 / 20

2.0

Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000

Related info for your journey

How long is the flight from Milan to Chicago?
Airlines like Scandinavian Airlines, ITA Airways, and United Airlines fly from Milan to Chicago in about 12h 30m. The time it takes to get you to your destination can typically vary by up to 12h 40m. 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 $626. British Airways is currently priced 23% 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 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: Qatar Airways (77%), Air Canada (75%), Austrian Airlines (75%).
What are the cheapest flights from Milan to Chicago?
Looking for the cheapest flight from Milan to Chicago? While on average our users pay $2,019, our data indicates the cheapest price to be $632. The most popular route (Milan Malpensa - Chicago O'Hare Intl), is priced around $500.
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 $484). 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

Merrillville

Lansing

Hammond

Porter

Benton Harbor

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
British Airways	Cheapest$525	Average$716	FlexibilityNo cancel fee	On-time70%
United Airlines	Cheapest$626	Average$952	FlexibilityNo cancel fee	On-time69%

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Cheap flights from Milan (MIL) to Chicago (CHI) - Compare and Save

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

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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 October 29, 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 October 29, 2025.

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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 October.

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.

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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 October 24, 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 October 29, 2025.

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

Reviews of airlines servicing Chicago

Get a feel of what it's like to fly with United Airlines, Aer Lingus, 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.

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?

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

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What are the cheapest flights from Milan to Chicago?

Can I find deals for flights from Milan to Chicago that include hotel bookings?

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

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Top 2 airlines flying from 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 October 29, 2025.